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{{Short description|Corticosteroid medication}} |
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{{drugbox |
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{{Use dmy dates|date=December 2023}} |
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| verifiedrevid = 407122155 |
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{{Use American English|date=July 2020}} |
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| IUPAC_name = (8''S'',9''R'',10''S'',11''S'',13''S'',14''S'',16''R'',17''R'')-9- Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16- trimethyl-6,7,8,9,10,11,12,13,14,15,16,17- dodecahydro-3''H''-cyclopentaphenanthren-3-one |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Infobox drug |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 443584169 |
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| image = Dexamethasone structure.svg |
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| image = Dexamethasone structure.svg |
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| width = 200 |
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| width = |
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| alt = Skeletal formula of dexamethasone |
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| image2 = Dexamethasone2.png |
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| image2 = Dexamethasone 3D ball.png |
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| width2 = 200 |
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| width2 = |
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| alt2 = Ball-and-stick model of the dexamethasone molecule |
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| caption = |
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<!-- Clinical data --> |
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| pronounce = |
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| tradename = Decadron, Ozurdex, Dexycu, others |
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| Drugs.com = {{drugs.com|monograph|dexamethasone}} |
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| MedlinePlus = a682792 |
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| DailyMedID = Dexamethasone |
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| pregnancy_AU = A |
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| pregnancy_AU_comment = <ref name="Drugs.com pregnancy" /> |
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| pregnancy_category = |
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| routes_of_administration = ], ], ], ], ], ], ] |
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| class = |
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| ATC_prefix = A01 |
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| ATC_suffix = AC02 |
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| ATC_supplemental = {{ATC|C05|AA09}}, {{ATC|D07|AB19}}, {{ATC|D10|AA03}}, {{ATC|H02|AB02}}, {{ATC|R01|AD03}}, {{ATC|S01|BA01}}, {{ATC|S02|BA06}}, {{ATC|S03|BA01}} |
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<!-- Legal status --> |
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| legal_AU = S4 |
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| legal_AU_comment = <ref>{{cite web |title=Dexamethasone Juno (Juno Pharmaceuticals Pty Ltd) |url=https://www.tga.gov.au/resources/prescription-medicines-registrations/dexamethasone-juno-juno-pharmaceuticals-pty-ltd |website=] |archive-url=https://web.archive.org/web/20230318025927/https://www.tga.gov.au/resources/prescription-medicines-registrations/dexamethasone-juno-juno-pharmaceuticals-pty-ltd |archive-date=18 March 2023 |url-status=live}}</ref> |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| legal_BR_comment = |
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| legal_CA = Rx-only |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = POM |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US_comment = <ref>{{cite web | title=Ozurdex- dexamethasone implant | website=DailyMed | date=30 October 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4b204f44-6e8a-4d17-803c-268f0b04679f | access-date=27 March 2022 | archive-date=27 March 2022 | archive-url=https://web.archive.org/web/20220327232705/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4b204f44-6e8a-4d17-803c-268f0b04679f | url-status=live }}</ref><ref>{{cite web | title=Dexamethasone sodium phosphate solution/ drops | website=DailyMed | date=31 July 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6bdcefbe-51e3-4ca4-afda-5aeca7b6fa73 | access-date=27 March 2022 | archive-date=27 January 2022 | archive-url=https://web.archive.org/web/20220127213839/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6bdcefbe-51e3-4ca4-afda-5aeca7b6fa73 | url-status=live }}</ref><ref>{{cite web | title=Dexycu- dexamethasone injection, suspension | website=DailyMed | date=20 December 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=583d70ed-bc42-465b-983d-c770db58406f | access-date=27 March 2022 | archive-date=27 March 2022 | archive-url=https://web.archive.org/web/20220327234559/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=583d70ed-bc42-465b-983d-c770db58406f | url-status=live }}</ref> |
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| legal_EU = Rx-only |
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| legal_EU_comment = <ref name="Ozurdex EPAR">{{cite web | title=Ozurdex EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/ozurdex | access-date=24 October 2020 | archive-date=27 October 2020 | archive-url=https://web.archive.org/web/20201027062744/https://www.ema.europa.eu/en/medicines/human/EPAR/ozurdex | url-status=live }}</ref><ref name="Neofordex EPAR">{{cite web | title=Neofordex EPAR | website=] (EMA) | date=25 July 2014 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/neofordex | archive-url=https://web.archive.org/web/20241007224603/https://www.ema.europa.eu/en/medicines/human/EPAR/neofordex | url-status=dead | archive-date=7 October 2024 | access-date=24 October 2020 }}</ref> |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = Rx-only |
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<!-- Pharmacokinetic data --> |
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| bioavailability = 80–90% |
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| protein_bound = 77% |
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| metabolism = ] |
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| metabolites = |
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| onset = |
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| elimination_half-life = biological half-life: 36 to 54 hours; plasma half-life: 4 to 5 hours<ref name="pmid31194457">{{cite journal | vauthors = Dogra P, Vijayashankar NP | title = Dexamethasone Suppression Test | journal = StatPearls | issue = 14 September 2020 | date = 14 September 2020 | pmid = 31194457}}</ref><ref name="pmid31808984">{{cite journal | vauthors = Jobe AH, Milad MA, Peppard T, Jusko WJ | title = Pharmacokinetics and Pharmacodynamics of Intramuscular and Oral Betamethasone and Dexamethasone in Reproductive Age Women in India | journal = Clinical and Translational Science | volume = 13 | issue = 2 | pages = 391–99 | date = March 2020 | pmid = 31808984 | pmc = 7070803 | doi = 10.1111/cts.12724}}</ref> |
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| duration_of_action = |
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| excretion = ] (65%) |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 50-02-2 |
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| CAS_supplemental = |
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| PubChem = 5743 |
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| IUPHAR_ligand = 2768 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB01234 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5541 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 7S5I7G3JQL |
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| UNII = 7S5I7G3JQL |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 |
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| KEGG = D00292 |
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| smiles = O=C(CO)3(O)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)CC42C3C)C)C |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = UREBDLICKHMUKA-CXSFZGCWBM |
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| ChEBI = 41879 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 384467 |
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| NIAID_ChemDB = |
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| PDB_ligand = DEX |
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| synonyms = |
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<!-- Chemical data --> |
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| IUPAC_name = (8''S'',9''R'',10''S'',11''S'',13''S'',14''S'',16''R'',17''R'')-9-Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3''H''-cyclopentaphenanthren-3-one |
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| C=22 | H=29 | F=1 | O=5 |
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| SMILES = O=C(CO)3(O)2(C(O)4(F)1(C(=CC(=O)C=C1)CC42C3C)C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 |
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| StdInChI = 1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 |
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| StdInChI_comment = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UREBDLICKHMUKA-CXSFZGCWSA-N |
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| StdInChIKey = UREBDLICKHMUKA-CXSFZGCWSA-N |
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| CAS_number = 50-02-2 |
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<!-- Physical data --> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| density = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| density_notes = |
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| ChemSpiderID = 5541 |
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| melting_point = 262 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| melting_high = |
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| ChEMBL = 384467 |
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| melting_notes = |
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| ATC_prefix = A01 |
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| boiling_point = |
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| ATC_suffix = AC02 |
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| boiling_notes = |
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| ATC_supplemental= {{ATC|C05|AA09}}, {{ATC|D07|AB19}}, {{ATC|H02|AB02}}, {{ATC|R01|AD03}}, {{ATC|S01|BA01}}, {{ATC|S02|BA06}}, {{ATC|S03|BA01}} |
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| solubility = |
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| ChEBI = 41879 |
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| PubChem = 5743 |
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| sol_units = |
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| specific_rotation = |
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| DrugBank = APRD00674 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00292 |
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| C = 22 |H = 29 |F = 1 |O = 5 |
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| molecular_weight = 392.461 g/mol |
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| bioavailability = 80-90% |
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| protein_bound = 70% |
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| metabolism = ] |
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| elimination_half-life = 36-54 hours |
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| excretion = renal |
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| pregnancy_AU = |
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| pregnancy_US = C |
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| pregnancy_category = |
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| legal_status = Rx-only |
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| routes_of_administration = Oral, ], ], ] and ] |
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}} |
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}} |
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<!-- Definition and uses --> |
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'''Dexamethasone''' is a potent synthetic member of the ] class of ] drugs. It acts as an ] and ]. It is 20 to 30 times more potent than the naturally occurring ] ] and 4 to 5 times more potent than ]. |
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'''Dexamethasone''' is a fluorinated ]<ref name=AHFS2015/> used to treat ], a number of ]s, severe ], ], ] (COPD), ], ], eye pain following ], ] (a complication of some forms of cancer),<ref>{{cite book| vauthors = Wilkinson IB |date = 13 July 2017 |title= Oxford Handbook of Clinical Medicine |page = 176 |publisher = OUP Oxford |isbn=978-0-19-968990-3 }}</ref> and along with ]s in ].<ref name=AHFS2015/> In ], it may be used in combination with a ] medication such as ].<ref name=AHFS2015/> In ], it may be used to improve outcomes in the baby.<ref name=AHFS2015/> It may be given ], as an ], as an ], as a topical cream or ointment for the skin or as a topical ophthalmic solution to the eye.<ref name=AHFS2015/> The effects of dexamethasone are frequently seen within a day and last for about three days.<ref name=AHFS2015>{{cite web|title=Dexamethasone|url=https://www.drugs.com/monograph/dexamethasone.html|publisher=The American Society of Health-System Pharmacists|access-date=29 July 2015|url-status=live|archive-url=https://web.archive.org/web/20170831175940/https://www.drugs.com/monograph/dexamethasone.html|archive-date=31 August 2017}}</ref> |
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<!-- Side effects and mechanism --> |
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The long-term use of dexamethasone may result in ], bone loss, ]s, easy bruising, or muscle weakness.<ref name=AHFS2015/> It is in ] C in the United States, meaning that it should only be used when the benefits are predicted to be greater than the risks.<ref name="Drugs.com pregnancy">{{cite web|title=Dexamethasone Use During Pregnancy|url=https://www.drugs.com/pregnancy/dexamethasone.html|website=Drugs.com|access-date=9 June 2016|quote=Dexamethasone is only recommended for use during pregnancy when there are no alternatives and benefit outweighs risk.|url-status=live|archive-url=https://web.archive.org/web/20160517153059/http://www.drugs.com/pregnancy/dexamethasone.html|archive-date=17 May 2016}}</ref> In Australia, the oral use is category A, meaning it has been frequently used in pregnancy and not been found to cause problems to the baby.<ref>{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm|work=Australian Government|access-date=22 April 2014|date=3 March 2014|quote=Drugs which have been taken by a large number of pregnant women and women of childbearing age without any proven increase in the frequency of malformations or other direct or indirect harmful effects on the fetus having been observed.|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm|archive-date=8 April 2014}}</ref> It should not be taken when ].<ref name=AHFS2015/> Dexamethasone has ] and ] effects.<ref name=AHFS2015/> |
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<!-- History, society and culture --> |
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Dexamethasone was first synthesized in 1957 by ] and was approved for medical use in 1958.<ref name="FDA Approval">{{cite web | title=Drugs@FDA: Dexamethasone | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=011664 | access-date=27 March 2022 | archive-date=30 November 2017 | archive-url=https://web.archive.org/web/20171130231459/https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=011664 | url-status=live }}</ref><ref name="RankovicHargreaves2012">{{cite book | vauthors = Rankovic Z, Hargreaves R, Bingham M |title=Drug discovery and medicinal chemistry for psychiatric disorders|date=2012|publisher=Royal Society of Chemistry|location=Cambridge|isbn=9781849733656|page=286|url=https://books.google.com/books?id=J4Mq3Lm1R7kC&pg=PA286|url-status=live|archive-url=https://web.archive.org/web/20160305022353/https://books.google.ca/books?id=J4Mq3Lm1R7kC&pg=PA286|archive-date=5 March 2016}}</ref><ref name=Fis2006>{{cite book |vauthors=Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=485 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 |access-date=17 June 2020 |archive-date=10 January 2023 |archive-url=https://web.archive.org/web/20230110032815/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 |url-status=live }}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> In 2022, it was the 234th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Dexamethasone Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Dexamethasone | access-date = 30 August 2024 }}</ref> It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref> In 2022, the combination of dexamethasone with ] and ] was the 274th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Dexamethasone; Neomycin; Polymyxin B Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/DexamethasoneNeomycinPolymyxinB | access-date = 30 August 2024 }}</ref> |
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==Medical uses== |
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] |
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==Therapeutic use== |
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===Anti-inflammatory=== |
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===Anti-inflammatory=== |
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] |
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Dexamethasone is used to treat many ] and ] conditions, such as ]. |
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Dexamethasone is used to treat many ] and ], such as ] and ].<ref>{{cite web | vauthors = Till J |title=Paramedic Clinical Training Aid |url= http://paramedic-info.com/PDA/index.html |access-date=30 August 2011 |url-status=dead |archive-url=https://web.archive.org/web/20120331110331/http://paramedic-info.com/PDA/index.html |archive-date=31 March 2012 }}</ref> ], a decrease in numbers of ]s due to an immune problem, responds to 40 mg daily for four days; it may be administered in 14-day cycles. It is unclear whether dexamethasone in this condition is significantly better than other ]s.<ref name="pmid19846889">{{cite journal | vauthors = Provan D, Stasi R, Newland AC, Blanchette VS, Bolton-Maggs P, Bussel JB, Chong BH, Cines DB, Gernsheimer TB, Godeau B, Grainger J, Greer I, Hunt BJ, Imbach PA, Lyons G, McMillan R, Rodeghiero F, Sanz MA, Tarantino M, Watson S, Young J, Kuter DJ | title = International consensus report on the investigation and management of primary immune thrombocytopenia | journal = Blood | volume = 115 | issue = 2 | pages = 168–86 | date = January 2010 | pmid = 19846889 | doi = 10.1182/blood-2009-06-225565 | doi-access = free }}</ref> |
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It is also given in small amounts<ref name="Schmelzeisen">{{cite journal |author=Schmelzeisen R, Frölich JC |title=Prevention of postoperative swelling and pain by dexamethasone after operative removal of impacted third molar teeth |journal=European Journal of Clinical Pharmacology |volume=44 |issue=3 |pages=275–277 |year=2004 |pmid= 8491244|doi=10.1007/BF00271371 |url=http://www.springerlink.com/content/m6158q104028nkl5/ }}</ref> (usually 5-6 tablets) before and/or after some forms of ], such as the extraction of the ], an operation which often leaves the patient with puffy, swollen cheeks. |
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It is also given in small amounts before and/or after some forms of ], such as the extraction of the ], an operation that often causes puffy, swollen cheeks.<ref name="pmid8491244">{{cite journal |vauthors=Schmelzeisen R, Frölich JC |year=1993 |title=Prevention of postoperative swelling and pain by dexamethasone after operative removal of impacted third molar teeth |journal=European Journal of Clinical Pharmacology |volume=44 |issue=3 |pages=275–77 |doi=10.1007/BF00271371 |pmid=8491244 |s2cid=12528750}}</ref> |
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Dexamethasone is commonly given as a treatment for ] in children.<ref name=":3" /> A single dose can reduce the swelling of the airway to improve breathing and reduce discomfort.<ref name=":3">{{cite web |url=https://www.mayoclinic.org/diseases-conditions/croup/diagnosis-treatment/drc-20350354 |title=Croup – Diagnosis & Treatment |website=Mayo Clinic |access-date=13 October 2017 |quote=Dexamethasone is usually recommended because of its long-lasting effects (up to 72 hours). |archive-date=10 October 2017 |archive-url=https://web.archive.org/web/20171010063045/http://www.mayoclinic.org/diseases-conditions/croup/diagnosis-treatment/drc-20350354 |url-status=live }}</ref> |
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It is injected into the heel when treating ], sometimes in conjunction with ]. |
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Dexamethasone is sometimes injected into the heel when treating ] or heel pain, sometimes in conjunction with ]. There is no evidence that this treatment helps in the long term, however, dexamethasone may provide short-term pain relief.<ref>{{cite journal | vauthors = Arnold MJ, Gruber J | title = Injected Corticosteroids for Plantar Heel Pain | language = en-US | journal = American Family Physician | volume = 97 | issue = 3 | pages = 169–170 | date = February 2018 | pmid = 29431981 | url = https://www.aafp.org/pubs/afp/issues/2018/0201/p169.html }}</ref> |
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It is useful to counteract allergic anaphylactic shock, if given in high doses. It is present in certain ] – particularly post-] drops – and as a ] (trade name ]), and certain ear drops (], when combined with an antibiotic and an antifungal). |
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It may be useful to counteract ], however this is not usually recommended by clinical guidelines.<ref>{{cite journal | vauthors = Dodd A, Hughes A, Sargant N, Whyte AF, Soar J, Turner PJ | title = Evidence update for the treatment of anaphylaxis | journal = Resuscitation | volume = 163 | pages = 86–96 | date = April 2021 | pmid = 33895231 | doi = 10.1016/j.resuscitation.2021.04.010 | pmc = 8139870 | hdl = 1983/82ab8f32-67a9-4277-8750-2246aabf5d96 | hdl-access = free }}</ref> |
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Dexamethasone is used in transvenous screw-in cardiac pacing leads to minimize the inflammatory response of the myocardium. The steroid is released into the myocardium as soon as the screw is extended and can play a significant role in minimizing the acute pacing threshold due to the reduction of inflammatory response. The typical quantity present in a lead tip is less than 1.0 mg. |
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It is present in certain ]s – particularly after ] – and as a ], and certain ear drops (can be combined with an antibiotic and an antifungal). Dexamethasone intravitreal steroid implants have been approved by the US ] (FDA) to treat ocular conditions such as ], ], and ]. However, the evidence is poor quality relating to the treatment of uveitis, with the potential side effects (] progression and raised ]) being significant, and the benefits not certainly greater than standard treatment.<ref>{{cite journal | vauthors = Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG | title = Corticosteroid implants for chronic non-infectious uveitis | journal = The Cochrane Database of Systematic Reviews | volume = 2023 | issue = 8 | pages = CD010469 | date = August 2023 | pmid = 37642198 | pmc = 10464657 | doi = 10.1002/14651858.CD010469.pub4 }}</ref> Dexamethasone has also been used with antibiotics to treat acute ].<ref>{{cite journal | vauthors = Emami S, Kitayama K, Coleman AL | title = Adjunctive steroid therapy versus antibiotics alone for acute endophthalmitis after intraocular procedure | journal = The Cochrane Database of Systematic Reviews | volume = 2022 | issue = 6 | pages = CD012131 | date = June 2022 | pmid = 35665485 | pmc = 9169535 | doi = 10.1002/14651858.CD012131.pub3 }}</ref> |
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Dexamethasone is often administered before antibiotics in cases of bacterial meningitis. It then acts to reduce the inflammatory response of the body to the bacteria killed by the antibiotics (bacterial death releases pro-inflammatory mediators that can cause a response which is harmful to the patient), thus improving prognosis and outcome.<ref>{{cite journal |author=van de Beek D, de Gans J, McIntyre P, Prasad K |editor1-last=Van De Beek |editor1-first=Diederik |title=Corticosteroids for acute bacterial meningitis |journal=Cochrane Database Syst Rev |volume= |issue=1 |pages=CD004405 |year=2007 |pmid=17253505 |doi=10.1002/14651858.CD004405.pub2 |url=http://mrw.interscience.wiley.com/cochrane/clsysrev/articles/CD004405/frame.html}}</ref> |
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Dexamethasone is used in transvenous screw-in ] to minimize the inflammatory response of the ]. The steroid is released into the myocardium as soon as the screw is extended and can play a significant role in minimizing the acute pacing threshold due to the reduction of inflammatory response. The typical quantity present in a lead tip is less than 1.0 mg.{{medcn|date=June 2020}} |
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===Oncologic uses=== |
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] patients undergoing ] are given Dexamethasone to counteract certain ] of their antitumor treatment. Dexamethasone can augment the ] effect of ] like ]. |
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Dexamethasone may be administered before antibiotics in cases of ]. ] — to which the causative agent of bacterial meningitis, ], belongs — have highly immunogenic ] as a component of their cell membrane and trigger a strong inflammatory response. Pre-administration of dexamethasone before the administration of antibiotics acts to reduce that response, thus reducing hearing loss and neurological damage.<ref>{{cite journal |vauthors=Brouwer MC, McIntyre P, Prasad K, van de Beek D |date=September 2015|title=Corticosteroids for acute bacterial meningitis |journal=Cochrane Database of Systematic Reviews |volume=2015 |issue=9 |pages=CD004405 |doi=10.1002/14651858.CD004405.pub5 |pmc=6491272 |pmid=26362566 |doi-access=free }}</ref> |
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In ]s (primary or metastatic), dexamethasone is used to counteract the development of ], which could eventually compress other brain structures. Dexamethasone is also given in ] where a tumor is compressing the spinal cord. |
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Dexamethasone is also used as a direct chemotherapeutic agent in certain ], especially in the treatment of ], in which dexamethasone is given alone or in combination with other chemotherapeutic drugs, including most commonly with ] (thal-dex), ], ] (Velcade; Vel-dex),<ref>{{Cite journal|url=http://www.haematologica.org/cgi/reprint/91/11/1498|title=Bortezomib plus dexamethasone as induction treatment prior to autologous stem cell transplantation in patients with newly diagnosed multiple myeloma: results of an IFM phase II study}}</ref> or a combination of ] (doxorubicin) and ] (VAD). |
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===Endocrine=== |
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===Cancer=== |
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People with ] undergoing ] are often given dexamethasone to counteract certain ] of their antitumor treatments. Dexamethasone can increase the ] effect of ], such as ].<ref name="PMID10824073">{{cite journal | vauthors = Roila F, Ballatori E, Ruggeri B, DeAngelis V | title = Dexamethasone alone or in combination with ondansetron for the prevention of delayed nausea and vomiting induced by chemotherapy | journal = The New England Journal of Medicine | volume = 342 | issue = 21 | pages = 1554–59 | date = May 2000 | pmid = 10824073 | doi = 10.1056/NEJM200005253422102 | doi-access = free }}</ref> The exact mechanism of this interaction is not well-defined, but it has been theorized that this effect may be due to, among many other causes, inhibition of ] synthesis, ] effects, ] effects, decreased release of ], or a combination of the aforementioned.<ref name="PMID12437261">{{cite journal | vauthors = Holte K, Kehlet H | title = Perioperative single-dose glucocorticoid administration: pathophysiologic effects and clinical implications | journal = Journal of the American College of Surgeons | volume = 195 | issue = 5 | pages = 694–712 | date = November 2002 | pmid = 12437261 | doi = 10.1016/s1072-7515(02)01491-6 }}</ref> |
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Dexamethasone is the treatment for the very rare disorder of ].<ref>{{cite journal |doi=10.1059/0003-4819-119-11-199312010-00009 |author=Chrousos GP, Detera-Wadleigh SD, Karl M |title=Syndromes of glucocorticoid resistance |journal=Ann Intern Med |volume=119 |issue=11 |pages=1113–24 |year=1993 |month=December |pmid=8239231 |url=http://www.annals.org/content/119/11/1113.full}}</ref><ref>{{cite journal |author=Charmandari E, Kino T, Ichijo T, Chrousos GP |title=Generalized glucocorticoid resistance: clinical aspects, molecular mechanisms, and implications of a rare genetic disorder |journal=J Clin Endocrinol Metab |volume=93 |issue=5 |pages=1563–72 |year=2008 |month=May |pmid=18319312 |pmc=2386273 |doi=10.1210/jc.2008-0040 |url=http://jcem.endojournals.org/cgi/content/full/93/5/1563}}</ref> |
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In ]s (primary or metastatic), dexamethasone is used to counteract the development of ], which could eventually compress other brain structures.<ref>{{cite journal | vauthors = Kostaras X, Cusano F, Kline GA, Roa W, Easaw J | title = Use of dexamethasone in patients with high-grade glioma: a clinical practice guideline | journal = Current Oncology | volume = 21 | issue = 3 | pages = e493–e503 | date = June 2014 | pmid = 24940109 | pmc = 4059813 | doi = 10.3747/co.21.1769 }}</ref> It is also given in ], where a tumor is compressing the spinal cord.{{medcn|date=June 2020}} Evidence on the safety and efficacy of using dexamethasone to treat malignant brain tumors is not clear.<ref name="pmid31346902">{{cite journal | vauthors = Jessurun CA, Hulsbergen AF, Cho LD, Aglio LS, Nandoe Tewarie RD, Broekman ML | title = Evidence-based dexamethasone dosing in malignant brain tumors: what do we really know? | journal = Journal of Neuro-Oncology | volume = 144 | issue = 2 | pages = 249–264 | date = September 2019 | pmid = 31346902 | pmc = 6700052 | doi = 10.1007/s11060-019-03238-4 | title-link = doi | doi-access = free }}</ref> |
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In ] and ], dexamethasone is prescribed when the person doesn't respond well to ] or ]. |
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Dexamethasone is also used as a direct chemotherapeutic agent in certain ], especially in the treatment of ], in which dexamethasone is given alone or in combination with other chemotherapeutic drugs, including most commonly with ] (Thal-dex), ], ] (Velcade, Vel-dex),<ref name="pmid17043025">{{cite journal | vauthors = Harousseau JL, Attal M, Leleu X, Troncy J, Pegourie B, Stoppa AM, Hulin C, Benboubker L, Fuzibet JG, Renaud M, Moreau P, Avet-Loiseau H | title = Bortezomib plus dexamethasone as induction treatment prior to autologous stem cell transplantation in patients with newly diagnosed multiple myeloma: results of an IFM phase II study | journal = Haematologica | volume = 91 | issue = 11 | pages = 1498–505 | date = November 2006 | pmid = 17043025 }} {{free access}}</ref> or a combination of ] (Adriamycin) and ] or ]/]/dexamethasone.{{medcn|date=June 2020}} |
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===Obstetrics=== |
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Dexamethasone may be given to women at risk of delivering prematurely in order to promote ] of the fetus' lungs. This has been associated with ], although not with increased rates of neonatal death.<ref>{{cite journal |author=Bloom SL, Sheffield JS, McIntire DD, Leveno KJ |title=Antenatal dexamethasone and decreased birth weight |journal=Obstet Gynecol |volume=97 |issue=4 |pages=485–90 |year=2001 |pmid=11275014 |url=http://www.greenjournal.org/cgi/content/full/97/4/485 |doi=10.1016/S0029-7844(00)01206-0 |format= – <sup></sup>}} {{Dead link|date=April 2009}}</ref> |
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===High altitude illnesses=== |
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===COVID-19=== |
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{{Anchor|COVID-19}} |
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Dexamethasone is used in the treatment of ] as well as pulmonary edema. It is commonly carried on mountain climbing expeditions to help climbers deal with altitude sickness. British mountain climber Peter Kinloch was provided with a shot of dexamethasone shortly before his death, after summiting Mount Everest.<ref name=MedicalProblems>{{cite journal |author=Cymerman, A; Rock, PB |title=Medical Problems in High Mountain Environments. A Handbook for Medical Officers |publisher=US Army Research Inst. of Environmental Medicine Thermal and Mountain Medicine Division Technical Report |volume=USARIEM-TN94-2 |url=http://archive.rubicon-foundation.org/7976 |accessdate=2010-09-06}}</ref><ref>{{cite journal| title=First-Line Therapy for Hypertension| journal=Annals of Internal Medicine |url=http://www.annals.org/cgi/reprint/146/8/615.pdf | |
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{{See also|COVID-19 drug repurposing research#Dexamethasone}} |
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date=April 17, 2007 |volume=146|page=615|issue=8}}</ref> |
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Dexamethasone is recommended by the ] in the UK and the ] (NIH) in the US for people with ] who need either ] or ] (without ventilation).<ref name=":0">{{Cite web|title=Dexamethasone and COVID-19|url=https://www.sps.nhs.uk/articles/dexamethasone-and-covid-19/|access-date=22 July 2020|website=SPS – Specialist Pharmacy Service|archive-date=22 July 2020|archive-url=https://web.archive.org/web/20200722082343/https://www.sps.nhs.uk/articles/dexamethasone-and-covid-19/|url-status=dead}}</ref><ref name=":1">{{Cite web|title=Corticosteroids|url=https://www.covid19treatmentguidelines.nih.gov/immune-based-therapy/immunomodulators/corticosteroids/|access-date=12 July 2020|website=COVID-19 Treatment Guidelines|publisher=National Institutes of Health|archive-date=19 July 2020|archive-url=https://web.archive.org/web/20200719163110/https://www.covid19treatmentguidelines.nih.gov/immune-based-therapy/immunomodulators/corticosteroids/|url-status=live}}</ref> |
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==Off-label use== |
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===Congenital adrenal hyperplasia=== |
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Dexamethasone has been used as an ] pre-natal treatment for the symptoms of ] (CAH) in female fetuses. CAH causes a variety of physical abnormalities, notably ] in girls. Early pre-natal CAH treatment has been shown to reduce some CAH symptoms, but it does not treat the underlying ]. |
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The ] (IDSA) guideline panel suggests the use of glucocorticoids for people with severe COVID-19, defined as people with ] ≤94% on room air, and those who require supplemental oxygen, mechanical ventilation, or ] (ECMO).<ref name="IDSA">{{cite web|title=COVID-19 Guideline, Part 1: Treatment and Management|url=https://www.idsociety.org/practice-guideline/covid-19-guideline-treatment-and-management/|access-date=22 July 2020|website=Infectious Diseases Society of America|quote=Recommendation 4. Among hospitalized people with severe* COVID-19, the IDSA guideline panel suggests glucocorticoids rather than no glucocorticoids. (Conditional recommendation, Moderate certainty of evidence)<br />Remark: Dexamethasone 6 mg IV or PO for 10 days (or until discharge if earlier) or equivalent glucocorticoid dose may be substituted if dexamethasone is unavailable. Equivalent total daily doses of alternative glucocorticoids to dexamethasone 6 mg daily are methylprednisolone 32 mg and prednisone 40 mg.<br />Recommendation 5. Among hospitalized people with COVID-19 without hypoxemia requiring supplemental oxygen, the IDSA guideline panel suggests against the use of glucocorticoids. (Conditional recommendation, Low certainty of evidence)|archive-date=6 October 2020|archive-url=https://web.archive.org/web/20201006214733/https://www.idsociety.org/practice-guideline/covid-19-guideline-treatment-and-management//|url-status=live}}</ref> The IDSA recommends against the use of glucocorticoids for those with COVID-19 without hypoxemia requiring supplemental oxygen.<ref name="IDSA" /> |
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A 2007 Swedish clinical trial found that treatment may cause cognitive and behavioural defects, but the small number of test subjects means the study cannot be considered definitive. Administration of pre-natal dexamethasone has been the subject of controversy over issues of ] and because treatment must predate a clinical diagnosis of CAH in the female fetus. |
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The treatment has also raised concerns in the LGBT community following an essay posted to the forum of the Hastings Center, a think tank devoted to bioethics, which quoted published research that suggested that pre-natal treatment of female fetuses could prevent those fetuses from becoming lesbians after birth, may make them more likely to engage in "traditionally" female-identified behaviour and careers, and more interested in bearing and raising children. Referring to a prospective father who attempted to mitigate the effects of the fraternal birth order effect on increasing the chances of homosexuality in male children by using a surrogate mother, the essay suggests that pre-natal "dex" treatments constitute the first known attempt to use an in utero method to attempt to reduce the incidence of homosexuality in humans<ref>{{Cite news |
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| last = Elton |
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| first = Catherine |
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| title = A Prenatal Treatment Raises Questions of Medical Ethics |
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| newspaper = '']'' |
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| date = 2010-06-18 |
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| url = http://www.time.com/time/health/article/0,8599,1996453,00.html?xid=rss-mostpopular |
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| accessdate = 2010-07-05}}</ref> |
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The ] (WHO) recommends systemic corticosteroids rather than no systemic corticosteroids for the treatment of people with COVID-19 (strong recommendation, based on moderate certainty evidence).<ref name="WHO guidance" /> The WHO suggests not to use corticosteroids in the treatment of people with non-severe COVID-19 (conditional recommendation, based on low certainty evidence).<ref name="WHO guidance" /> |
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A medical consensus in 2010 by the Endocrine Society and affiliated organizations indicated that prenatal dexamethasone for CAH should be regarded as experimental and should only be used in Institutional Review Board-approved controlled clinical trials at centers large enough to collect meaningful data.<ref>{{ cite video|url=http://www.nxtbook.com/tristar/endo/day4_2010/index.php?startid=8}}</ref> |
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The ] ] issued a press release announcing preliminary results that the drug could reduce deaths by about a third in participants on ]s and by about a fifth in participants on oxygen; it did not benefit people who did not require respiratory support.<ref name="oxford news">{{cite news|date=16 June 2020|title=Dexamethasone reduces death in hospitalized people with severe respiratory complications of COVID-19|website=University of Oxford|url=http://www.ox.ac.uk/news/2020-06-16-dexamethasone-reduces-death-hospitalised-patients-severe-respiratory-complications|access-date=16 June 2020|archive-date=16 June 2020|archive-url=https://web.archive.org/web/20200616145052/http://www.ox.ac.uk/news/2020-06-16-dexamethasone-reduces-death-hospitalised-patients-severe-respiratory-complications/|url-status=live}}</ref> A ] of seven clinical trials of critically ill COVID-19 participants, each treated with one of three different ]s found a statistically significant reduction in death.<ref name="Sterne 2020"/> The largest reduction was obtained with dexamethasone (36% compared to placebo).<ref name="Sterne 2020">{{cite journal | vauthors = Sterne JA, Murthy S, Diaz JV, Slutsky AS, Villar J, Angus DC, Annane D, Azevedo LC, Berwanger O, Cavalcanti AB, Dequin PF, Du B, Emberson J, Fisher D, Giraudeau B, Gordon AC, Granholm A, Green C, Haynes R, Heming N, Higgins JP, Horby P, Jüni P, Landray MJ, Le Gouge A, Leclerc M, Lim WS, Machado FR, McArthur C, Meziani F, Møller MH, Perner A, Petersen MW, Savovic J, Tomazini V, Veiga VC, Webb S, Marshall JC | collaboration = The WHO Rapid Evidence Appraisal for COVID-19 Therapies (REACT) Working Group | title = Association Between Administration of Systemic Corticosteroids and Mortality Among Critically Ill Patients With COVID-19: A Meta-analysis | journal = JAMA | date = September 2020 | volume = 324 | issue = 13 | pages = 1330–1341 | doi = 10.1001/jama.2020.17023 | pmid = 32876694 | pmc = 7489434 | s2cid = 221467783 | doi-access = free }}</ref><ref>{{cite journal | title = Corticosteroids in COVID-19 ARDS: Evidence and Hope During the Pandemic | vauthors = Prescott HC, Rice TW | journal = JAMA | date = September 2020 | volume = 324 | issue = 13 | pages = 1292–1295 | doi = 10.1001/jama.2020.16747 | pmid = 32876693 | s2cid = 221468015 | url = https://jamanetwork.com/journals/jama/fullarticle/2770275 | doi-access = free | access-date = 2 September 2020 | archive-date = 3 December 2020 | archive-url = https://web.archive.org/web/20201203011845/https://jamanetwork.com/journals/jama/fullarticle/2770275 | url-status = live }}</ref> |
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===Abuses=== |
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Dexamethasone has also been used in the hope of enhancing sports performance.<ref>{{Cite web|url=http://www.fis-ski.com/data/document/info-kowalczyk.pdf |date=June 13, 2005|title= FIS Doping Control statement on Kowalcyzk (Digitized version)|accessdate=July 30, 2006}}</ref> |
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In September 2020, the ] (EMA) endorsed the use of dexamethasone in adults and adolescents, from twelve years of age and weighing at least {{convert|40|kg|lb}}, who require supplemental oxygen therapy.<ref name="EMA PR">{{cite press release | title=EMA endorses use of dexamethasone in COVID-19 patients on oxygen or mechanical ventilation | website=] (EMA) | date=18 September 2020 | url=https://www.ema.europa.eu/en/news/ema-endorses-use-dexamethasone-covid-19-patients-oxygen-mechanical-ventilation | access-date=21 September 2020 | archive-date=14 February 2021 | archive-url=https://web.archive.org/web/20210214060918/https://www.ema.europa.eu/en/news/ema-endorses-use-dexamethasone-covid-19-patients-oxygen-mechanical-ventilation | url-status=live }} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> Dexamethasone can be taken by mouth or given as an injection or infusion (drip) into a vein.<ref name="EMA PR" /> |
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Long term use of dexamethasone under the brand name Oradexon is widespread among ]s in Bangladesh in spite of the dangers, because it helps them develop fat easily, an attractive feature in this poor country.<ref>{{Cite news|url=http://www.guardian.co.uk/society/2010/apr/05/sex-workers-bangladesh-steroid|title= A new danger for sex workers in Bangladesh|publisher= The Guardian|date= 5 April 2010}}</ref><ref>{{Cite news|url=http://news.bbc.co.uk/2/hi/world/south_asia/10173115.stm|title= Bangladesh's dark brothel steroid secret|publisher=BBC News|date=30 May 2010}}</ref> |
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In November 2020, the ]'s Clinical Pharmacology Task Group recommended dexamethasone for hospitalized patients requiring mechanical ventilation.<ref>{{Cite web |last=Public Health Agency of Canada |date=23 November 2020 |title=Ad-hoc COVID-19 Clinical Pharmacology Task Group: Statement on dexamethasone |url=https://www.canada.ca/en/public-health/corporate/mandate/about-agency/external-advisory-bodies/list/covid-19-clinical-pharmacology-task-group/statement-dexamethasone.html#a5 |url-status=dead |archive-url=https://archive.today/20201227053419/https://www.canada.ca/en/public-health/corporate/mandate/about-agency/external-advisory-bodies/list/covid-19-clinical-pharmacology-task-group/statement-dexamethasone.html%23a5 |archive-date=27 December 2020 |access-date=1 April 2022 |website=Government of Canada }}</ref> Although dexamethasone, and other glucocorticoids, reduce mortality in COVID-19 they have also been associated with an increased risk of secondary infections,<ref>{{cite journal | vauthors = Conway Morris A, Kohler K, De Corte T, Ercole A, De Grooth HJ, Elbers PW, Povoa P, Morais R, Koulenti D, Jog S, Nielsen N, Jubb A, Cecconi M, De Waele J | title = Co-infection and ICU-acquired infection in COIVD-19 ICU patients: a secondary analysis of the UNITE-COVID data set | journal = Critical Care | volume = 26 | issue = 1 | pages = 236 | date = August 2022 | pmid = 35922860 | pmc = 9347163 | doi = 10.1186/s13054-022-04108-8 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Meynaar IA, van Rijn S, Ottens TH, van Burgel ND, van Nieuwkoop C | title = Increased risk of central line-associated bloodstream infection in COVID-19 patients associated with dexamethasone but not with interleukin antagonists | journal = Intensive Care Medicine | volume = 48 | issue = 7 | pages = 954–957 | date = July 2022 | pmid = 35670819 | pmc = 9171741 | doi = 10.1007/s00134-022-06750-w }}</ref><ref>{{cite journal | vauthors = Scaravilli V, Guzzardella A, Madotto F, Beltrama V, Muscatello A, Bellani G, Monti G, Greco M, Pesenti A, Bandera A, Grasselli G | title = Impact of dexamethasone on the incidence of ventilator-associated pneumonia in mechanically ventilated COVID-19 patients: a propensity-matched cohort study | journal = Critical Care | volume = 26 | issue = 1 | pages = 176 | date = June 2022 | pmid = 35698155 | pmc = 9191402 | doi = 10.1186/s13054-022-04049-2 | doi-access = free }}</ref> secondary infections being a significant issue in critically ill COVID-19 patients.<ref>{{cite journal | vauthors = Maes M, Higginson E, Pereira-Dias J, Curran MD, Parmar S, Khokhar F, Cuchet-Lourenço D, Lux J, Sharma-Hajela S, Ravenhill B, Hamed I, Heales L, Mahroof R, Soderholm A, Forrest S, Sridhar S, Brown NM, Baker S, Navapurkar V, Dougan G, Bartholdson Scott J, Conway Morris A | title = Ventilator-associated pneumonia in critically ill patients with COVID-19 | journal = Critical Care | volume = 25 | issue = 1 | pages = 25 | date = January 2021 | pmid = 33430915 | pmc = 7797892 | doi = 10.1186/s13054-021-03460-5 | doi-access = free }}</ref> |
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==Diagnostic use== |
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Dexamethasone is also used in a diagnostic context, namely in its property to suppress the natural ]. |
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Patients presenting with clinical signs of glucocorticoid excess (]) are generally diagnosed by a 24-hour urine collection for cortisol or by a ]. During the latter, the response of the body to a high dose of glucocorticoids is monitored. Various forms are performed. In the most common form, a patient takes a nighttime dose of either 1 or 4 mg of dexamethasone, and the serum cortisol levels are measured in the morning. If the levels are relatively high (over 5 µg/dL or 150 nmol/L), then the test is positive and the patient has an autonomous source of either ] or ], indicating Cushing's syndrome where the tumor does not have a feedback mechanism. If ACTH levels are lowered by at least 50%, this would indicate ], since the ] has a feedback mechanism that has been reset to a higher level of cortisol. Longer versions rely on urine collections on oral dexamethasone over various days. |
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The mechanism of action of dexamethasone involves suppression of late-stage ] programs in severe COVID-19 patients.<ref>{{cite journal | vauthors = Sinha S, Rosin NL, Arora R, Labit E, Jaffer A, Cao L, Farias R, Nguyen AP, de Almeida LG, Dufour A, Bromley A, McDonald B, Gillrie MR, Fritzler MJ, Yipp BG, Biernaskie J | title = Dexamethasone modulates immature neutrophils and interferon programming in severe COVID-19 | journal = Nature Medicine | volume = 28 | issue = 1 | pages = 201–211 | date = January 2022 | pmid = 34782790 | pmc = 8799469 | doi = 10.1038/s41591-021-01576-3 | s2cid = 244132637 }}</ref> |
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==Veterinary use== |
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Combined with ] and ], dexamethasone is available under the name ''Aurizon '', ] 115550-35-1, and used to treat difficult ear infections, especially in dogs. It can also be combined with ] to treat horses with swelling of ] limbs and general ].<ref name="wedgewood">{{cite web |url=http://www.wedgewoodpharmacy.com/monographs/trichlormethiazide.asp |title=Trichlormethiazide and Dexamethasone for veterinary use | author= | publisher=Wedgewood Pharmacy |accessdate=2008-01-23 |format= |work=}}</ref> |
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=== Surgery === |
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Dexamethasone is used fairly regularly, often as a single intravenous dose, during surgery to prevent postoperative nausea and vomiting, manage pain, potentially reduce the amount of pain medication required, and help reduce post-surgery hospitalisation time.<ref name=":2" /> The adverse effects of taking steroids after surgery on wound healing, blood sugar levels, and in diabetics are not completely understood; however, dexamethasone likely does not increase the risk of postoperative infections.<ref name=":2" /><ref name=":2">{{cite journal | vauthors = Polderman JA, Farhang-Razi V, Van Dieren S, Kranke P, DeVries JH, Hollmann MW, Preckel B, Hermanides J | title = Adverse side effects of dexamethasone in surgical patients | journal = The Cochrane Database of Systematic Reviews | volume = 11 | issue = 11 | pages = CD011940 | date = November 2018 | pmid = 30480776 | pmc = 6426282 | doi = 10.1002/14651858.CD011940.pub3 }}</ref> |
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===Endocrine=== |
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Dexamethasone is the treatment for the very rare disorder of ].<ref name="pmid8239231">{{cite journal | vauthors = Chrousos GP, Detera-Wadleigh SD, Karl M | title = Syndromes of glucocorticoid resistance | journal = Annals of Internal Medicine | volume = 119 | issue = 11 | pages = 1113–24 | date = December 1993 | pmid = 8239231 | doi = 10.7326/0003-4819-119-11-199312010-00009 | url = http://annals.org/pdfaccess.ashx?url=/data/journals/aim/19786/0000605-199312010-00009.pdf | access-date = 4 July 2020 | url-status = dead | s2cid = 26040431 | archive-url = https://web.archive.org/web/20170814034732/http://annals.org/pdfaccess.ashx?url=%2Fdata%2Fjournals%2Faim%2F19786%2F0000605-199312010-00009.pdf | archive-date = 14 August 2017 }}</ref><ref name="pmid18319312">{{cite journal | vauthors = Charmandari E, Kino T, Ichijo T, Chrousos GP | title = Generalized glucocorticoid resistance: clinical aspects, molecular mechanisms, and implications of a rare genetic disorder | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 93 | issue = 5 | pages = 1563–72 | date = May 2008 | pmid = 18319312 | pmc = 2386273 | doi = 10.1210/jc.2008-0040 }}</ref> |
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In ] and ], dexamethasone is prescribed when the patient does not respond well to ] or ].{{medcn|date=June 2020}} |
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It can be used in ] in older adolescents and adults to suppress ] (ACTH) production. It is typically given at night.<ref>Dan L. Longo, Anthony Fauci, Dennis Kasper, Stephen Hauser, J. Jerry Jameson and Joseph Loscalzo, , 18th edition, p. 3055</ref> |
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===Pregnancy=== |
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Dexamethasone may be given to women at risk of delivering prematurely to promote ] of the fetus's lungs. This administration, given from one day to one week before delivery, has been associated with ], although not with increased rates of neonatal death.<ref name="pmid11275014">{{cite journal | vauthors = Bloom SL, Sheffield JS, McIntire DD, Leveno KJ | title = Antenatal dexamethasone and decreased birth weight | journal = Obstetrics and Gynecology | volume = 97 | issue = 4 | pages = 485–90 | date = April 2001 | pmid = 11275014 | doi = 10.1016/S0029-7844(00)01206-0 | s2cid = 33601749 }}</ref> |
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Dexamethasone has also been used during pregnancy as an ] prenatal treatment for the symptoms of ] (CAH) in female babies. CAH causes a variety of physical abnormalities, notably ]. Early prenatal CAH treatment has been shown to reduce some CAH symptoms, but it does not treat the underlying ]. This use is controversial: it is inadequately studied, only around one in ten of the fetuses of women treated are at risk of the condition, and serious adverse events have been documented.<ref>{{Cite web|url=http://content.time.com/time/health/article/0,8599,1996453,00.html|archive-url=https://web.archive.org/web/20160831150342/http://content.time.com/time/health/article/0,8599,1996453,00.html|url-status=dead|title=A Prenatal Treatment Raises Questions of Medical Ethics| vauthors = Elton C |date=18 June 2010|archive-date=31 August 2016|via=content.time.com}}</ref> Experimental use of dexamethasone in pregnancy for fetal CAH treatment was discontinued in Sweden when one in five cases had adverse events.<ref>{{cite journal | vauthors = Hirvikoski T, Nordenström A, Wedell A, Ritzén M, Lajic S | title = Prenatal dexamethasone treatment of children at risk for congenital adrenal hyperplasia: the Swedish experience and standpoint | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 97 | issue = 6 | pages = 1881–83 | date = June 2012 | pmid = 22466333 | doi = 10.1210/jc.2012-1222 | doi-access = free }}</ref> |
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A small clinical trial found long-term effects on verbal working memory among the small group of children treated prenatally, but the small number of test subjects means the study cannot be considered definitive.<ref name="Hirvikoski_2007">{{cite journal | vauthors = Hirvikoski T, Nordenström A, Lindholm T, Lindblad F, Ritzén EM, Wedell A, Lajic S | title = Cognitive functions in children at risk for congenital adrenal hyperplasia treated prenatally with dexamethasone | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 92 | issue = 2 | pages = 542–48 | date = February 2007 | pmid = 17148562 | doi = 10.1210/jc.2006-1340 | doi-access = free }}</ref><ref name="pmid21164263">{{cite journal | vauthors = Lajic S, Nordenström A, Hirvikoski T | journal = Endocrine Development| title = Long-term outcome of prenatal dexamethasone treatment of 21-hydroxylase deficiency | volume = 20 | pages = 96–105 | year = 2011 | pmid = 21164263 | doi = 10.1159/000321228 | isbn = 978-3-8055-9643-5 }}</ref> |
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===High-altitude illnesses=== |
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Dexamethasone is used in the treatment of ] (HACE), as well as ] (HAPE).<ref name="pmid29959871">{{cite journal |vauthors=Simancas-Racines D, Arevalo-Rodriguez I, Osorio D, Franco JV, Xu Y, Hidalgo R |title=Interventions for treating acute high altitude illness |journal=Cochrane Database Syst Rev |volume=6 |issue= 12|pages=CD009567 |date=June 2018 |pmid=29959871 |pmc=6513207 |doi=10.1002/14651858.CD009567.pub2 |url= }}</ref> It is commonly carried on mountain-climbing expeditions to help climbers deal with complications of ].<ref name=MedicalProblems>{{cite book | vauthors = Cymerman A, Rock PB | title = Medical Problems in High Mountain Environments. A Handbook for Medical Officers | publisher = US Army Research Inst. of Environmental Medicine Thermal and Mountain Medicine Division Technical Report | volume = USARIEM-TN94-2 | url = http://operationalmedicine.org/TextbookFiles/highmountain.pdf#page=19&zoom=auto,-76,314 | archive-url = https://web.archive.org/web/20170617133159/http://operationalmedicine.org/TextbookFiles/highmountain.pdf#page=19&zoom=auto,-76,314 | url-status = dead | archive-date = 17 June 2017 | access-date = 17 June 2020 | year = 1994 }}</ref><ref name="pmid17438328">{{cite journal | vauthors = Eledrisi MS | title = First-line therapy for hypertension | journal = Annals of Internal Medicine | volume = 146 | issue = 8 | pages = 615 | date = April 2007 | pmid = 17438328 | doi = 10.7326/0003-4819-146-8-200704170-00021 }}</ref> |
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===Nausea and vomiting=== |
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Intravenous dexamethasone is effective for the prevention of nausea and vomiting in people who had surgery and whose post-operative pain was treated with long-acting spinal or epidural spinal opioids.<ref>{{cite journal | vauthors = Grape S, Usmanova I, Kirkham KR, Albrecht E | title = Intravenous dexamethasone for prophylaxis of postoperative nausea and vomiting after administration of long-acting neuraxial opioids: a systematic review and meta-analysis | journal = Anaesthesia | volume = 73 | issue = 4 | pages = 480–89 | date = April 2018 | pmid = 29226971 | doi = 10.1111/anae.14166 | doi-access = free }}</ref> |
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The combination of dexamethasone and a ] such as ] is more effective than a 5-HT<sub>3</sub> receptor antagonist alone in preventing postoperative nausea and vomiting.<ref name="pmid16670361">{{cite journal | vauthors = Kovac AL | title = Meta-analysis of the use of rescue antiemetics following PONV prophylactic failure with 5-HT3 antagonist/dexamethasone versus single-agent therapies | journal = The Annals of Pharmacotherapy | volume = 40 | issue = 5 | pages = 873–87 | date = May 2006 | pmid = 16670361 | doi = 10.1345/aph.1G338 | s2cid = 32843029 }}</ref> |
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===Sore throat=== |
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A single dose of dexamethasone or another steroid speeds the improvement of a ].<ref>{{cite journal | vauthors = Sadeghirad B, Siemieniuk RA, Brignardello-Petersen R, Papola D, Lytvyn L, Vandvik PO, Merglen A, Guyatt GH, Agoritsas T | title = Corticosteroids for treatment of sore throat: systematic review and meta-analysis of randomised trials | journal = BMJ | volume = 358 | pages = j3887 | date = September 2017 | pmid = 28931508 | pmc = 5605780 | doi = 10.1136/bmj.j3887 }}</ref> |
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==Contraindications== |
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==Contraindications== |
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]s of dexamethasone include,<ref name=MSR>{{cite web|title=Decadron, Dexamethasone Intensol (dexamethasone) dosing, indications, interactions, adverse effects, and more|work=Medscape Reference|publisher=WebMD|access-date=11 December 2013|url=http://reference.medscape.com/drug/decadron-dexamethasone-intensol-dexamethasone-342741#showall|url-status=live|archive-url=https://web.archive.org/web/20131212220123/http://reference.medscape.com/drug/decadron-dexamethasone-intensol-dexamethasone-342741#showall|archive-date=12 December 2013}}</ref><ref name = TGAO/> but are not limited to: |
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Some of these ] are relative: |
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* Uncontrolled infections |
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* Existing gastrointestinal ] |
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* Known hypersensitivity to dexamethasone |
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* Cushing's syndrome |
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* ] |
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* Severe forms of heart insufficiency |
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* Severe ] |
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* Systemic ] |
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* Concurrent treatment with ] (including ]) |
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* Uncontrolled ] |
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* Systemic ] |
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* Severe systemic viral, bacterial, and fungal infections |
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* Preexisting wide angle ] |
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* ] |
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==Side effects== |
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==Adverse effects== |
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The exact incidence of the adverse effects of dexamethasone is not available, hence estimates have been made as to the incidence of the adverse effects below based on the adverse effects of related corticosteroids and on available documentation on dexamethasone.<ref name=TGAO>{{cite web|title=Product Information Dexamethsone (dexamethasone)|work=TGA eBusiness Services|publisher=Aspen Pharmacare Australia Pty Ltd|date=10 August 2010|access-date=11 December 2013|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-06682-3|format=PDF|archive-date=28 January 2017|archive-url=https://web.archive.org/web/20170128131300/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-06682-3|url-status=live}} (Accept terms and conditions to open PDF, which doesn't work in archived version)</ref><ref name=TGAI>{{cite web|title=Product Information Dexmethsone Injection|work=TGA eBusiness ServicesAspen Pharmacare Australia Pty Ltd|publisher=Aspen Pharmacare Australia Pty Ltd|date=2 March 2011|access-date=11 December 2013|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2011-PI-02528-3|format=PDF|archive-date=29 January 2017|archive-url=https://web.archive.org/web/20170129093042/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2011-PI-02528-3|url-status=live}} (Accept terms and conditions to open PDF, which doesn't work in archived version)</ref><ref name=DM>{{cite web|title=Dexamethasone tablet |work=DailyMed|publisher=ECR Pharmaceuticals|date=December 2010|access-date=11 December 2013|url=http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=428cc7bb-e0f9-466c-b38f-11ac22cda752|url-status=live|archive-url=https://web.archive.org/web/20131213040029/http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=428cc7bb-e0f9-466c-b38f-11ac22cda752|archive-date=13 December 2013}}</ref><ref name=EMCT>{{cite web|title=Dexamethasone Tablet BP 2.0 mg – Summary of Product Characteristics (SPC)|work=electronic Medicines Compendium|publisher=Merck Sharp & Dohme Limited|date=26 January 2018|access-date=17 June 2020|url=https://www.medicines.org.uk/emc/product/5411/smpc|archive-date=17 June 2020|archive-url=https://web.archive.org/web/20200617215029/https://www.medicines.org.uk/emc/product/5411/smpc|url-status=live}}</ref><ref name=EMCI>{{cite web|title=Dexamethasone 4.0 mg/ml injection – Summary of Product Characteristics (SPC)|work=electronic Medicines Compendium|publisher=Merck Sharp & Dohme Limited|date=4 December 2013|access-date=11 December 2013|url=http://www.medicines.org.uk/emc/medicine/8369/SPC/Dexamethasone+4.0mg+ml+injection/|url-status=dead|archive-url=https://web.archive.org/web/20150508054341/http://www.medicines.org.uk/emc/medicine/8369/SPC/Dexamethasone+4.0mg+ml+injection/|archive-date=8 May 2015}}</ref> |
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If dexamethasone is given orally or by injection (]) over a period of more than a few days, side-effects common to systemic ] may occur. These may include: |
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* Stomach upset, increased sensitivity to stomach acid to the point of ulceration of esophagus, stomach, and duodenum |
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* Increased appetite leading to significant weight gain |
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* A latent ] often becomes manifest. Glucose intolerance is worsened in patients with preexisting diabetes. |
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* Immunsuppressant action, particularly if given together with other immunosuppressants such as ]. Bacterial, viral, and fungal disease may progress more easily and can become life-threatening. Fever as a warning symptom is often suppressed. |
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* Psychiatric disturbances, including personality changes, irritability, euphoria, mania |
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* Osteoporosis under long term treatment, pathologic fractures (e.g., hip) |
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* Muscle atrophy, negative protein balance (]) |
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* Elevated liver enzymes, fatty liver degeneration (usually reversible) |
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* ] (syndrome resembling hyperactive adrenal cortex with increase in ], hypertension, bone demineralization, etc.) |
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* Depression of the adrenal gland is usually seen, if more than 1.5 mg daily are given for more than three weeks to a month. |
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* Hypertension, fluid and sodium retention, edema, worsening of heart insufficiency (due to mineral corticoid activity) |
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* Dependence with withdrawal syndrome is frequently seen. |
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* Increased intraocular pressure, certain types of glaucoma, cataract (serious clouding of eye lenses) |
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* Dermatologic: Acne, allergic dermatitis, dry scaly skin, ] and ], ], impaired wound-healing, increased sweating, rash, ], suppression of reactions to skin tests, thin fragile skin, thinning scalp hair, ]. |
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* Allergic reactions (though infrequently): ], ], ]. |
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===Common=== |
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Other side effects have been noted, and should cause concern if they are more than mild. |
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{{Div col}} |
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* ] |
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* ] |
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* ] |
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* ] (in long-term treatment, occurs in about 10% of patients) |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (in long-term treatment, occurs in about 11% of patients) |
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* ] |
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* ] |
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* Impaired ] and ] |
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* ] |
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* Increased risk of viral, bacterial, fungal, and parasitic infections |
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* ] |
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* ] |
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* ] |
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* steroid induced ] and ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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{{Div col end}} |
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===Unknown frequency=== |
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The short time treatment for allergic reaction, shock, and diagnostic purposes usually does not cause serious side effects. |
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{{Div col}} |
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* ] |
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* ] |
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* ] (including ]) |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] or ]l thinning |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (in children) |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (with long-term treatment) |
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* ] |
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* ] |
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* ] |
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* ] (inflammation of the pancreas) |
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* ] |
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* ] |
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* ] (causing nitrogen depletion) |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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{{Div col end}} |
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===Withdrawal=== |
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Novelist ] believed his first book, '']'' was a side effect of ] Dexamethasone giving him both "formidable energy" while quelling his creative doubts.<ref>] 4 April 2009 ''Michael Cox: Publisher's editor who scored a...'' </ref> |
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Sudden withdrawal after long-term treatment with corticosteroids can lead to<ref name = TGAO/> |
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{{Div col|colwidth=18em}} |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] (painful, itchy skin condition) |
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* ] |
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* ] |
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{{Div col end}} |
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==Interactions== |
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==Interactions== |
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Known drug interactions include:<ref name = TGAO/> |
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* NSAIDs and alcohol: increased risk of gastrointestinal ulceration |
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* Inducers of hepatic microsomal enzymes such as ], ], and ] can reduce the ] of dexamethasone.{{medcn|date=June 2020}} |
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* Mineralocorticoids: increased risk of hypertension, edema and heart problems |
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* Cotreatment with oral contraceptives can increase its ].{{medcn|date=June 2020}} |
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* Oral antidiabetic drugs and insulin: antidiabetic therapy may have to be adjusted |
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==Pharmacology== |
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Other interactions (with certain antibiotics, estrogens, ephedrine, digoxin) are known. |
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{{see also|Glucocorticoid#Pharmacology}} |
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===Pharmacodynamics=== |
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==Dosage== |
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As a glucocorticoid, dexamethasone is an ] of the ] (GR).<ref name="pmid17045197">{{cite journal | vauthors = Cole TJ | title = Glucocorticoid action and the development of selective glucocorticoid receptor ligands | journal = Biotechnol Annu Rev | series = Biotechnology Annual Review | volume = 12 | issue = | pages = 269–300 | date = 2006 | pmid = 17045197 | doi = 10.1016/S1387-2656(06)12008-6 | isbn = 9780444527240 | url = }}</ref> It is highly ] for the GR over the ] (MR),<ref name="pmid27967238">{{cite journal | vauthors = Meijer OC, de Kloet ER | title = A Refill for the Brain Mineralocorticoid Receptor: The Benefit of Cortisol Add-On to Dexamethasone Therapy | journal = Endocrinology | volume = 158 | issue = 3 | pages = 448–454 | date = March 2017 | pmid = 27967238 | doi = 10.1210/en.2016-1495 | s2cid = 7311584 | url = | doi-access = free }}</ref> and in relation to this, has minimal ] activity.<ref name="pmid25905379">{{cite book | vauthors = De Groot LJ, Chrousos G, Dungan K, Feingold KR, Grossman A, Hershman JM, Koch C, Korbonits M, McLachlan R, New M, Purnell J, Rebar R, Singer F, Vinik A, Nicolaides NC, Pavlaki AN, Maria Alexandra MA, Chrousos GP | title = Glucocorticoid Therapy and Adrenal Suppression | chapter = Endotext | year = 2000 | publisher = MDText.com | pmid = 25905379 | chapter-url = https://www.ncbi.nlm.nih.gov/books/NBK279156/ | access-date = 17 June 2020 | archive-date = 1 July 2020 | archive-url = https://web.archive.org/web/20200701151045/https://www.ncbi.nlm.nih.gov/books/NBK279156/ | url-status = live }}</ref><ref name="pmid16178782" /><ref name="pmid23947590">{{cite journal | vauthors = Liu D, Ahmet A, Ward L, Krishnamoorthy P, Mandelcorn ED, Leigh R, Brown JP, Cohen A, Kim H | title = A practical guide to the monitoring and management of the complications of systemic corticosteroid therapy | journal = Allergy, Asthma, and Clinical Immunology | volume = 9 | issue = 1 | pages = 30 | date = August 2013 | pmid = 23947590 | pmc = 3765115 | doi = 10.1186/1710-1492-9-30 | doi-access = free }}</ref> This is in contrast to ] corticosteroids like ], which bind to and activate both the GR and the MR.<ref name="pmid27967238" /> Dexamethasone is 25 times more ] than ] (cortisol) as a glucocorticoid.<ref name="pmid17045197" /> Its ] (K<sub>i</sub>) for the GR was about 1.2{{nbsp}}nM in one study.<ref name="pmid17045197" /> |
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* Shock: 4 to 8 mg intravenously initially, repeat if necessary to a total dose of 24 mg. |
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* Autoimmune diseases and inflammations: longterm therapy with 0.5 to 1.5 mg oral per day. Avoid more than 1.5 mg daily, because serious side effects are more frequently encountered with higher doses. |
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* Adjuvant to or part of chemotherapy: individual schedule |
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* Diagnostic purposes: special schedule |
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The activation of the GR by dexamethasone results in ] suppression of the ] (HPA axis) and of production of endogenous corticosteroids by the ]s, thereby reducing circulating endogenous concentrations of corticosteroids like cortisol and ].<ref name="pmid27967238" /> |
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==Synthesis== |
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To synthesise dexamethasone, 16β-methylprednisolone acetate is dehydrated to the 9,11 dehydro derivative. This is then reacted with a source of hypobromite such as basic N-bromosuccinimide to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring opening reaction with ] in ] gives dexamethasone.<ref>{{Cite journal|doi=10.1021/ja01545a063|year=1958|last1=Arth|first1=Glen E.|last2=Fried|first2=John|last3=Johnston|first3=David B. R.|last4=Hoff|first4=Dale R.|last5=Sarett|first5=Lewis H.|last6=Silber|first6=Robert H.|last7=Stoerk|first7=Herbert C.|last8=Winter|first8=Charles A.|journal=Journal of the American Chemical Society|volume=80|pages=3161|issue=12}}</ref> |
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<ref>{{Cite journal|doi=10.1021/ja01549a095|year=1958|last1=Taub|first1=D.|last2=Hoffsommer|first2=R. D.|last3=Slates|first3=H. L.|last4=Wendler|first4=N. L.|journal=Journal of the American Chemical Society|volume=80|pages=4435|issue=16}}</ref> |
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Dexamethasone poorly penetrates the ] into the ] due to binding to ].<ref name="pmid27967238" /><ref name="pmid9787252">{{cite journal | vauthors = De Kloet ER | title = Why Dexamethasone Poorly Penetrates in Brain | journal = Stress | volume = 2 | issue = 1 | pages = 13–20 | date = October 1997 | pmid = 9787252 | doi = 10.3109/10253899709014734 | url = }}</ref> However, higher doses of dexamethasone override the export capacity of P-glycoprotein and enter the brain to produce central activation of GRs.<ref name="pmid27967238" /> In conjunction with the suppression of endogenous corticosteroids by dexamethasone, this results in skewed ratios of activation of peripheral versus central GRs as well as skewed ratios of activation of GRs versus MRs when compared to non-] corticosteroids.<ref name="pmid27967238" /><ref name="pmid9787252" /> These differences can have significant clinical relevance.<ref name="pmid27967238" /><ref name="pmid9787252" /> |
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] |
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==References== |
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==Chemistry== |
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Dexamethasone is a ] ] ] and ] of ] (hydrocortisone) and is also known as 1-dehydro-9α-fluoro-16α-methylhydrocortisone or as 9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA366|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=366–|url-status=live|archive-url=https://web.archive.org/web/20170215024945/https://books.google.com/books?id=0vXTBwAAQBAJ|archive-date=15 February 2017}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA310|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=310–|url-status=live|archive-url=https://web.archive.org/web/20170824142254/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA310|archive-date=24 August 2017}}</ref> The ] and ] of dexamethasone has been determined by ].<ref>{{ cite journal | vauthors = Raynor JW, Minor W, Chruszcz M | year = 2007 | title = Dexamethasone at 119 K | journal = Acta Crystallographica Section E | volume = 63 | issue = 6 | pages = o2791–93 | doi = 10.1107/S1600536807020806 | bibcode = 2007AcCrE..63o2791R }}</ref> It is a ] of ], the two compounds differing only in the spatial configuration of the ] at position 16 (see ]).<ref>{{cite journal | vauthors = Antignac JP, Le Bizec B, Monteau F, Andre F | title = Differentiation of betamethasone and dexamethasone using liquid chromatography/positive electrospray tandem mass spectrometry and multivariate statistical analysis | journal = Journal of Mass Spectrometry | volume = 37 | issue = 1 | pages = 69–75 | date = January 2002 | pmid = 11813313 | doi = 10.1002/jms.260 | bibcode = 2002JMSp...37...69A }}</ref> |
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{{Reflist|2}} |
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==External links== |
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===Synthesis=== |
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To synthesize dexamethasone, 16β-methylprednisolone acetate is ] to the 9,11-dehydro ].<ref>{{Cite journal | vauthors = Arth GE, Fried J, ((Johnston DBR)), Hoff DR, Sarett HL, Silber RH, Stoerk HC, Winter CA | journal = Journal of the American Chemical Society | year = 1958 | volume = 80 | pages = 3161–63 | issue = 12 | title = 16-Methylated steroids. II. 16α-Methyl analogs of cortisone, a new group of anti-inflammatory steroids. 9α-Halo derivatives | doi = 10.1021/ja01545a063 | bibcode = 1958JAChS..80.3161A }}</ref><ref>{{Cite journal |vauthors=Taub D, Hoffsommer RD, Slates HL, lWendler NL | title = 16β-Methyl cortical steroids | journal = Journal of the American Chemical Society |year=1958 | volume = 80 | pages = 4435 | issue=16|doi=10.1021/ja01549a095| bibcode = 1958JAChS..80.4435T }}</ref> This is then reacted with a source of ], such as basic ], to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with ] in ] gives dexamethasone.{{citation needed|date=June 2020}} |
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* {{Cite web|url=http://www.myeloma.org/main.jsp?source=link&source_link_id=2117&type=article&tab_id=13&menu_id=94&id=1749|title= Understanding Dexamethasone and Other Steroids}} |
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* {{cite web|url=http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Dexamethasone |publisher=U.S. National Library of Medicine: Drug Information Portal |title= Dexamethasone}} |
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{{Corticosteroids}} |
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{{Stomatological preparations}} |
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=== Spectroscopy === |
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{{Vasoprotectives}} |
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In chemistry, ] is used to analyze products of reactions. To understand if dexamethasone is synthesized from a reaction, spectroscopy must be taken and compared to the literature spectrum. There are multiple spectroscopy analyses that can be taken including ], ], ], ], and ]<gallery mode="nolines" widths="400" heights="350" caption="NMR spectrum for dexamethasone"> |
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File:1H NMR for Dexamethasone.png|'''1H NMR for Dexamethasone <ref name=":4">Speakman, N. M. A., Heard, A. W., & Nitschke, J. R. (2024). A CuI6L4 Cage Dynamically Reconfigures to Form Suitanes and Selectively Bind Fluorinated Steroids. Journal of the American Chemical Society, 146(15), 10234–10239. https://doi.org/10.1021/jacs.4c00257</ref>''' |
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File:13C NMR for Dexamethasone.png|'''13C NMR for Dexamethasone <ref name=":4" />''' |
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</gallery>The NMR spectrum shown above can be used to compare to product synthesized through reactions to figure out if Dexamethasone was synthesized. 1H NMR, among other things, shows that there are 29 hydrogens and 13C NMR shows that there are 22 carbons. |
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<gallery widths="400" heights="350"> |
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File:Infrared spectroscopy of Dexamethasone.png|'''Infrared spectroscopy of Dexamethasone <ref>Shing, C. (2023). ''Novel cocrystals of dexamethasone''. Hong Kong:</ref>''' |
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File:UV-vis spectroscopy of Dexamethasone.png|'''UV-vis spectroscopy of Dexamethasone <ref>Takegami, S., Kitamura, K., Funakoshi, T., & Kitade, T. (2008). Partitioning of anti-inflammatory steroid drugs into phosphatidylcholine and phosphatidylcholine-cholesterol small unilamellar vesicles as studied by second-derivative spectrophotometry. ''Chemical and Pharmaceutical Bulletin, 56''(5), 663–667. {{doi|10.1248/cpb.56.663}}</ref>''' |
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</gallery> |
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Using IR spectroscopy, the peaks show the functional groups found in the molecule. You can see peaks at 3472, 1662, and 1618 representing alcohol, aldehyde, and alkene functional groups. UV-vis spectroscopy is another way to analyze a product to figure out what it is. |
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Finally, mass spectroscopy showed peaks at: 393.1, 355.2 147.1 m/z. The peak at 393.1 m/z is the peak for dexamethasone as its molecular weight is 392.46 m/z. <ref>Mulabagal, V., Wilson, C., & Hayworth, J. S. (2017). An ultrahigh-performance chromatography/tandem mass spectrometry quantitative method for trace analysis of potential endocrine disrupting steroid hormones in estuarine sediments. ''Rapid Communications in Mass Spectrometry, 31''(5), 419–429. {{doi|10.1002/rcm.7807}}</ref> |
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==History== |
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Dexamethasone was first ] by ] in 1957.<ref name="targetcivils">{{Cite web|url=https://targetcivils.in/1089/|title=Dexamethasone|date=17 June 2020|access-date=18 June 2020|archive-date=1 October 2020|archive-url=https://web.archive.org/web/20201001110933/https://targetcivils.in/1089/|url-status=dead}}</ref><ref name="RankovicHargreaves2012"/> It was introduced for medical use in 1958.<ref name="pmid16178782">{{cite journal | vauthors = Khan MO, Park KK, Lee HJ | title = Antedrugs: an approach to safer drugs | journal = Current Medicinal Chemistry | volume = 12 | issue = 19 | pages = 2227–39 | year = 2005 | pmid = 16178782 | doi = 10.2174/0929867054864840 }}</ref> |
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On 16 June 2020, the ] announced preliminary results stating that dexamethasone improves survival rates of hospitalized patients with ] receiving oxygen or on a ]. Benefits were only observed in patients requiring respiratory support; those who did not require breathing support saw a worse survival rate than the control group, although the difference may have been due to chance.<ref name="gnpi">{{cite web|date=16 June 2020|title=Dexamethasone in COVID-19|url=https://www.gpni.co.uk/wp-content/uploads/2020/06/DEXAMETHASONE-IN-COVID-19.pdf|access-date=18 June 2020|website=www.gpni.co.uk|archive-date=17 June 2020|archive-url=https://web.archive.org/web/20200617192738/https://www.gpni.co.uk/wp-content/uploads/2020/06/DEXAMETHASONE-IN-COVID-19.pdf|url-status=live}}</ref> |
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A preprint containing the full dataset was published on 22 June 2020, and demand for dexamethasone surged after the publication of the preprint.<ref>{{cite journal|vauthors=Mahase E|date=June 2020|title=Covid-19: Demand for dexamethasone surges as RECOVERY trial publishes preprint|journal=BMJ|volume=369|pages=m2512|doi=10.1136/bmj.m2512|pmid=32576548|doi-access=free}}</ref> The preliminary report was published in '']'' on 18 July 2020.<ref name="NEJM-17July20">{{cite journal | vauthors=Horby P, Lim WS, Emberson JR, Mafham M, Bell JL, Linsell L, Staplin N, Brightling C, Ustianowski A, Elmahi E, Prudon B, Green C, Felton T, Chadwick D, Rege K, Fegan C, Chappell LC, Faust SN, Jaki T, Jeffery K, Montgomery A, Rowan K, Juszczak E, Baillie JK, Haynes R, Landray MJ | date=July 2020 | title=Dexamethasone in Hospitalized Patients with Covid-19 – Preliminary Report | journal=New England Journal of Medicine | volume=384 | issue=8 | pages=693–704 | doi=10.1056/NEJMoa2021436 | pmid=32678530 | pmc=7383595 | doi-access=free | title-link=doi }}</ref> The final report was published in February 2021.<ref>{{cite journal | vauthors = Horby P, Lim WS, Emberson JR, Mafham M, Bell JL, Linsell L, Staplin N, Brightling C, Ustianowski A, Elmahi E, Prudon B, Green C, Felton T, Chadwick D, Rege K, Fegan C, Chappell LC, Faust SN, Jaki T, Jeffery K, Montgomery A, Rowan K, Juszczak E, Baillie JK, Haynes R, Landray MJ | title = Dexamethasone in Hospitalized Patients with Covid-19 | journal = N Engl J Med | volume = 384 | issue = 8 | pages = 693–704 | date = February 2021 | pmid = 32678530 | pmc = 7383595 | doi = 10.1056/NEJMoa2021436 | doi-access = free | title-link = doi }}</ref> |
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The ] (WHO) states that dexamethasone should be reserved for seriously ill and critical patients receiving COVID-19 treatment in a hospital setting,<ref name="Reuters 17Jun20">{{cite news|date=17 June 2020|title=Important to use dexamethasone only for serious COVID cases – WHO|url=https://www.reuters.com/article/us-health-coronavirus-who-dexamethasone/important-to-use-dexamethasone-only-for-serious-covid-cases-who-idUSKBN23O2MT|access-date=18 June 2020|archive-date=17 June 2020|archive-url=https://web.archive.org/web/20200617200600/https://www.reuters.com/article/us-health-coronavirus-who-dexamethasone/important-to-use-dexamethasone-only-for-serious-covid-cases-who-idUSKBN23O2MT|url-status=live}}</ref> and the WHO Director-General stated that "WHO emphasizes that dexamethasone should only be used for patients with severe or critical disease, under close clinical supervision. There is no evidence this drug works for patients with mild disease or as a preventative measure, and it could cause harm."<ref name="WHO DG 22 June 2020">{{cite web|title=WHO Director-General's opening remarks at the media briefing on COVID-19|date=22 June 2020|url=https://www.who.int/dg/speeches/detail/who-director-general-s-opening-remarks-at-the-media-briefing-on-covid-19---22-june-2020|access-date=26 June 2020|website=World Health Organization|archive-date=12 September 2020|archive-url=https://web.archive.org/web/20200912202605/https://www.who.int/dg/speeches/detail/who-director-general-s-opening-remarks-at-the-media-briefing-on-covid-19---22-june-2020|url-status=live}}</ref> In July 2020, the WHO stated they were in the process of updating treatment guidelines to include dexamethasone or other steroids.<ref>{{Cite web|title=Q&A: Dexamethasone and COVID-19|url=https://www.who.int/news-room/q-a-detail/q-a-dexamethasone-and-covid-19|access-date=12 July 2020|website=] (WHO)|archive-date=11 October 2020|archive-url=https://web.archive.org/web/20201011115730/https://www.who.int/news-room/q-a-detail/q-a-dexamethasone-and-covid-19/|url-status=live}}</ref> In September 2020, the WHO released updated guidance on using corticosteroids for COVID-19.<ref name="WHO guidance">{{cite report | vauthors=((World Health Organization)) | year=2020 | title=Corticosteroids for COVID-19: living guidance, 2 September 2020 | publisher=World Health Organization | hdl=10665/334125 | id=WHO/2019-nCoV/Corticosteroids/2020.1 | url=https://www.who.int/publications/i/item/WHO-2019-nCoV-Corticosteroids-2020.1 | access-date=2 September 2020 | archive-date=11 October 2020 | archive-url=https://web.archive.org/web/20201011091829/https://www.who.int/publications/i/item/WHO-2019-nCoV-Corticosteroids-2020.1 | url-status=live }}</ref><ref>{{cite press release | title=WHO updates clinical care guidance with corticosteroid recommendations | website=] (WHO) | date=2 September 2020 | url=https://www.who.int/news-room/feature-stories/detail/who-updates-clinical-care-guidance-with-corticosteroid-recommendations | access-date=27 March 2022 | archive-date=6 May 2021 | archive-url=https://web.archive.org/web/20210506094931/https://www.who.int/news-room/feature-stories/detail/who-updates-clinical-care-guidance-with-corticosteroid-recommendations | url-status=live }}</ref> |
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In July 2020, the ] (EMA) started reviewing results from the RECOVERY study arm that involved the use of dexamethasone in the treatment of patients with COVID-19 admitted to the hospital to provide an opinion on the results and in particular the potential use of dexamethasone for the treatment of adults with COVID-19.<ref name="EMA review">{{cite press release | title=EMA starts review of dexamethasone for treating adults with COVID-19 requiring respiratory support | website=] (EMA) | date=24 July 2020 | url=https://www.ema.europa.eu/en/news/ema-starts-review-dexamethasone-treating-adults-covid-19-requiring-respiratory-support | access-date=27 July 2020 | archive-date=30 January 2021 | archive-url=https://web.archive.org/web/20210130205543/https://www.ema.europa.eu/en/news/ema-starts-review-dexamethasone-treating-adults-covid-19-requiring-respiratory-support | url-status=live }} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref><ref>{{cite news | title=EMA to review results from study testing common steroid drug against COVID-19 | website=Reuters | date=24 July 2020 | url=https://www.reuters.com/article/us-health-coronavirus-ema-dexamethasone-idUSKCN24P1KH | access-date=27 July 2020 | archive-date=27 July 2020 | archive-url=https://web.archive.org/web/20200727203429/https://www.reuters.com/article/us-health-coronavirus-ema-dexamethasone-idUSKCN24P1KH | url-status=live }}</ref> In September 2020, the EMA received an application for marketing authorization of dexamethasone for COVID-19.<ref>{{cite web | title=EMA receives application for marketing authorisation of Dexamethasone Taw COVID-19 | website=] (EMA) | date=2 September 2020 | url=https://www.ema.europa.eu/en/news/ema-receives-application-marketing-authorisation-dexamethasone-taw-covid-19 | access-date=2 September 2020 | archive-date=3 September 2020 | archive-url=https://web.archive.org/web/20200903082812/https://www.ema.europa.eu/en/news/ema-receives-application-marketing-authorisation-dexamethasone-taw-covid-19 | url-status=live }}</ref> |
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==Society and culture== |
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===Price=== |
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Dexamethasone is inexpensive.<ref name=WHODex>{{cite web|title=Dexamethasone for Accelerating Lung Maturation in Preterm Babies |url=https://www.who.int/selection_medicines/committees/expert/19/applications/Dexamethasone_29_C_NI.pdf|access-date=29 July 2015|url-status=live|archive-url=https://web.archive.org/web/20151222111212/http://www.who.int/selection_medicines/committees/expert/19/applications/Dexamethasone_29_C_NI.pdf|archive-date=22 December 2015}}</ref> In the United States a month of medication is typically priced less than {{US$|25}}.<ref name=AHFS2015/> In India, a course of treatment for preterm labor is about {{US$|0.50}}.<ref name=WHODex/> The drug is available in most areas of the world.<ref name=WHODex/> |
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===Nonmedical use=== |
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Dexamethasone is given in ], causing weight gain aimed at making them appear older and healthier to customers and police.<ref name="BBC_News_2010-05-30">{{cite web | vauthors = Dummett M |date=30 May 2010 |title=Bangladesh's dark brothel steroid secret |publisher=] |url=https://www.bbc.co.uk/news/10173115 |url-status=live |archive-url=https://web.archive.org/web/20120222194217/http://www.bbc.co.uk/news/10173115 |archive-date=22 February 2012 }}</ref> |
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Dexamethasone and most ]s are banned by sporting bodies including the ].<ref>{{cite web | url = https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition/glucocorticoids | title = Prohibited In-Competition: Glucocorticoids | publisher = World Anti-Doping Agency | access-date = 16 July 2018 | archive-date = 16 July 2018 | archive-url = https://web.archive.org/web/20180716170139/https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition/glucocorticoids | url-status = dead }}</ref> |
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==Veterinary use== |
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Combined with ] ] 115550-35-1and ], dexamethasone is available under the name Aurizon, ] 50-02-2, and used to treat difficult ear infections, especially in dogs. It can also be combined with ] to treat horses with swelling of ] limbs and general ].<ref name="wedgewood">{{cite web |url=http://www.wedgewoodpharmacy.com/monographs/trichlormethiazide.asp |title=Trichlormethiazide and Dexamethasone for veterinary use |publisher=Wedgewood Pharmacy |access-date=23 January 2008 |url-status=live |archive-url=https://web.archive.org/web/20071212125537/http://www.wedgewoodpharmacy.com/monographs/trichlormethiazide.asp |archive-date=12 December 2007 }}</ref> |
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== References == |
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{{Reflist}} |
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== External links == |
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{{Commons category|Dexamethasone}} |
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* {{cite web | title=Dexamethasone Ophthalmic | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a682869.html }} |
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* {{cite web | title=Dexamethasone Injection | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a616022.html }} |
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