| Revision as of 10:47, 9 April 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 482537657 of page Betamethasone_dipropionate for the Chem/Drugbox validation project (updated: 'ChEBI', 'StdInChI', 'StdInChIKey', 'ChEMBL', 'CAS_... |
Latest revision as of 12:39, 25 April 2024 edit Dkapetansky (talk | contribs)Extended confirmed users730 editsm →Pharmacokinetics |
| Line 1: |
Line 1: |
|
|
{{Short description|Glucocorticoid steroid (chemical compound)}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
{{Infobox drug |
|
{{Drugbox |
|
|
|
| Verifiedfields = changed |
|
| IUPAC_name = phenanthren-17-yl] propanoate |
|
|
|
| verifiedrevid = 486407176 |
|
| image = Betamethasone_dipropionate.png |
|
|
|
| drug_name = |
|
|
| INN = |
|
|
| type = <!-- empty --> |
|
|
| image = Betamethasone_dipropionate.svg |
|
|
| image2 = Betamethasone-dipropionate-from-xtal-Mercury-3D-balls-thin.png |
|
|
| width = |
|
|
| alt = |
|
|
| caption = |
|
|
|
|
|
<!--Clinical data--> |
|
<!-- Clinical data --> |
|
| tradename = |
|
| pronounce = |
|
|
| tradename = Diprolene, Sernivo, Diprosone, others |
|
| Drugs.com = {{drugs.com|monograph|betamethasone}} |
|
| Drugs.com = {{drugs.com|monograph|betamethasone}} |
|
|
| MedlinePlus = a682799 |
|
| pregnancy_category = |
|
|
|
| licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) --> |
|
| legal_status = |
|
|
|
| licence_EU = <!-- EMA uses INN (or special INN_EMA) --> |
|
| routes_of_administration = topical |
|
|
|
| DailyMedID = Betamethasone_dipropionate |
|
|
| licence_US = <!-- FDA may use generic or brand name (generic name preferred) --> |
|
|
| pregnancy_AU = B3 |
|
|
| pregnancy_AU_comment = |
|
|
| pregnancy_US = <!-- A / B / C / D / X / N --> |
|
|
| pregnancy_US_comment = |
|
|
| pregnancy_category= |
|
|
| dependency_liability = |
|
|
| addiction_liability = |
|
|
| routes_of_administration = ] |
|
|
| class = |
|
|
| ATCvet = |
|
|
| ATC_prefix = A07 |
|
|
| ATC_suffix = EA04 |
|
|
| ATC_supplemental = {{ATC|C05|AA05}} {{ATC|D07|AC01}} {{ATC|D07|XC01}} {{ATC|H02|AB01}} {{ATC|R01|AD06}} {{ATC|R03|BA04}} {{ATC|S01|BA06}} {{ATC|S01|CB04}} {{ATC|S02|BA07}} {{ATC|S03|BA03}} {{ATC|D07|CC01}} {{ATC|S01|CA05}} {{ATC|S03|CA06}} {{ATC|D07|BC01}} {{ATC|S01|BB04}} |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
<!-- Legal status --> |
|
| bioavailability = |
|
| legal_AU = S4 |
|
| protein_bound = |
|
| legal_AU_comment = |
|
|
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F--> |
|
| metabolism = |
|
|
|
| legal_BR_comment = |
|
| elimination_half-life = |
|
|
|
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
|
|
| legal_CA_comment = |
|
|
| legal_DE = <!-- Anlage I, II, III or Unscheduled--> |
|
|
| legal_DE_comment = |
|
|
| legal_NZ = <!-- Class A, B, C --> |
|
|
| legal_NZ_comment = |
|
|
| legal_UK = POM |
|
|
| legal_UK_comment = <ref>{{cite web | title=Diprosone Cream - Summary of Product Characteristics (SmPC) | work = Electronic Medicines Compendium (EMC) | publisher = Datapharm Ltd. | date=19 September 2019 | url=https://www.medicines.org.uk/emc/product/6405/smpc | access-date=14 April 2020}}</ref> |
|
|
| legal_US = Rx-only |
|
|
| legal_US_comment = |
|
|
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV--> |
|
|
| legal_UN_comment = |
|
|
| legal_status = <!-- For countries not listed above --> |
|
|
|
|
|
<!--Identifiers--> |
|
<!-- Pharmacokinetic data --> |
|
|
| bioavailability = |
|
| CAS_number = <!-- blanked - oldvalue: 5593-20-4 --> |
|
|
| ATC_prefix = |
|
| protein_bound = |
|
| ATC_suffix = |
|
| metabolism = |
|
|
| metabolites = |
|
| ATC_supplemental = |
|
|
|
| onset = |
|
| ChEBI = 31276 |
|
|
|
| elimination_half-life = |
|
| StdInChI = 1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 |
|
|
|
| duration_of_action = |
|
| StdInChIKey = CIWBQSYVNNPZIQ-XYWKZLDCSA-N |
|
|
|
| excretion = |
|
|
|
|
|
<!-- Identifiers --> |
|
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
|
| CAS_number = 5593-20-4 |
|
|
| CAS_supplemental = |
|
| PubChem = 21800 |
|
| PubChem = 21800 |
|
| DrugBank = |
|
| IUPHAR_ligand = |
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
|
| DrugBank = DBSALT000851 |
|
|
| DrugBank2_Ref = {{drugbankcite|correct|drugbank}} |
|
|
| DrugBank2 = DB00443 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 20490 |
|
| ChemSpiderID = 20490 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| ChEMBL = <!-- blanked - oldvalue: 1200384 --> |
|
|
|
| UNII = 826Y60901U |
|
| C=28 | H=37 | F=1 | O=7 |
|
|
|
| KEGG_Ref = |
|
| molecular_weight = 504.59 g/mol |
|
|
|
| KEGG = D01637 |
|
| smiles = O=C(OCC(=O)3(OC(=O)CC)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)CC42C3C)C)C)CC |
|
|
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| InChI = 1/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 |
|
|
|
| ChEBI = 31276 |
|
| InChIKey = CIWBQSYVNNPZIQ-XYWKZLDCBG |
|
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 1200384 |
|
|
| NIAID_ChemDB = |
|
|
| PDB_ligand = |
|
| synonyms = Betamethasone-17,21-dipropionate |
|
| synonyms = Betamethasone-17,21-dipropionate |
|
|
|
|
|
<!-- Chemical and physical data --> |
|
|
| IUPAC_name = phenanthren-17-yl] propanoate |
|
|
| C=28 | H=37 | F=1 | O=7 |
|
|
| SMILES = O=C(OCC(=O)3(OC(=O)CC)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)CC42C3C)C)C)CC |
|
|
| Jmol = |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChI = 1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1 |
|
|
| StdInChI_comment = |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
| StdInChIKey = CIWBQSYVNNPZIQ-XYWKZLDCSA-N |
|
|
| density = |
|
|
| density_notes = |
|
|
| melting_point = |
|
|
| melting_high = |
|
|
| melting_notes = |
|
|
| boiling_point = |
|
|
| boiling_notes = |
|
|
| solubility = |
|
|
| sol_units = |
|
|
| specific_rotation = |
|
}} |
|
}} |
|
|
|
|
|
'''Betamethasone dipropionate''' is a ] ] with ] and ] properties. It is applied as a ] cream, ointment, lotion or gel ('''Diprolene''') to treat ] and other skin conditions such as ]. Minor side effects include dry skin and mild, temporary stinging when applied.<ref name="brand">{{cite web | url = https://www.drugs.com/sfx/betamethasone-dipropionate-side-effects.html | title = Betamethasone Dipropionate Side Effects | work = ] }}</ref> Betamethasone dipropionate is a "super high potency" corticosteroid used to treat inflammatory skin conditions such as ], ] and ]. It is a synthetic analog of the adrenal corticosteroids. Although its exact mechanism of action is not known, it is effective when applied topically to cortico-responsive inflammatory dermatoses.<ref name="drugs.com"/> It is available as a ].<ref>{{cite web | title=Betamethasone Monograph for Professionals | website=Drugs.com | date=26 December 2019 | url=https://www.drugs.com/monograph/betamethasone.html | access-date=15 August 2020}}</ref> |
|
|
|
|
|
==Adverse effects== |
|
|
Although the absorption of betamethasone dipropionate is small, when used for prolonged periods of time (periods exceeding two weeks), or across a large surface area (total use greater than 50 grams per week), it can have adverse effects. One such effect is the ability of the corticosteroid to suppress the ].<ref name="drugs.com"/><ref name = "RxList">{{cite web | title = Diprolene Ointment | url = http://www.rxlist.com/diprolene-ointment-drug/indications-dosage.htm#D | work = RxList | date = 29 June 2021 }}</ref> This can lead to a depression in the release of adrenal hormones such as ] and ], or ACTH. Symptoms of HPA axis suppression are often subtle and variable, but can often be detected using simple blood or urine tests such at ACTH stimulation test or urinary free cortisol.<ref name = "RxList" /> Those at increased risk for HPA axis suppression are those who are more likely to absorb more of the steroid through the skin. These groups include: |
|
|
*Those who have used topical corticosteroids over a prolonged period of time |
|
|
*Those who have used corticosteroids to cover a large surface area |
|
|
*Those with broken skin barrier or extensive abrasions |
|
|
*Those who have recently undergone stress (such as illness, trauma, surgery) |
|
|
*Children under the age of 12 |
|
|
|
|
|
HPA axis suppression is preventable by supplementation with glucocorticosteroids. If HPA axis suppression occurs, it is often reversed shortly after discontinuation of treatment.<ref>{{cite web | vauthors = Ault A | date = 25 March 2005 | title = Adrenal Suppression From Topical Corticosteroids Surprisingly High| url = http://www.medpagetoday.com/Dermatology/Steroids/777 | archive-url = https://web.archive.org/web/20160301074517/http://www.medpagetoday.com/Dermatology/Steroids/777 | archive-date = 1 March 2016 | work = MedPage Today }}</ref> |
|
|
|
|
|
==Pharmacology== |
|
|
|
|
|
===Mechanism of action=== |
|
|
{{further|Glucocorticoid#Mechanism of action}} |
|
|
|
|
|
===Pharmacokinetics=== |
|
|
Absorption of topical corticosteroids depends on several factors such as the vehicle, or delivery system used by the drug, the integrity of the epidermal barrier, and whether or not an occlusive bandage is used in combination with the drug.<ref name="drugs.com">{{cite web | title = Diprolene | url = https://www.drugs.com/pro/diprolene.html#dosage | work = Drugs.com | date = 1 June 2021 }}</ref> |
|
|
|
|
|
The absorption of topical betamethasone dipropionate is theoretically minuscule; however, if absorbed it follows the same pharmacokinetic profile as is typical of systemic corticosteroids. It is metabolized primarily by the liver by hydrolysis to its metabolites B17P (primary) and ] and the 6β-hydroxy derivatives of those metabolites, and it is excreted primarily by the kidneys.<ref name="drugs.com"/><ref name=Enstilar>{{cite web | title = Enstilar (calcipotriene and betamethasone dipropionate) Foam, 0.005%/0.064% for topical use. Full Prescribing Information | url = http://enstilar.com/pdf/enstilar-pi.pdf | location = Parsippany, NJ | publisher = LEO Pharma Inc | date = 2015 | access-date = 2015-11-21 | archive-date = 2018-09-20 | archive-url = https://web.archive.org/web/20180920190124/http://enstilar.com/pdf/enstilar-pi.pdf | url-status = dead }}</ref> |
|
|
|
|
|
==Chemistry== |
|
|
Betamethasone dipropionate is a white to almost white crystalline powder.{{medcn|date=April 2020}} |
|
|
|
|
|
==Regulation== |
|
|
Betamethasone dipropionate was patented by ] in 1987, as an augmented cream/lotion, Diprolene in the U.S., and Disprosone in Europe.<ref>, "Profile for Tradename: Diprolene AF", ''DrugPatentWatch.com</ref> These patents expired in 2003 and 2007 respectively leading to generic production of betamethasone dipropionate. During this time other topical corticosteroids such as ] and ] also became available as generic creams. Merck filed for "pediatric exclusivity" in 2001 launching a clinical trial to prove betamethasone dipropionate's safety and efficacy for use in pediatrics.<ref>{{cite web | title = Diprolene Pediatric Exclusivity | url = http://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-555S008_Diprosone_admindocs.pdf | work = Centerfor Drug Evaluation and Research | publisher = U.S. Food and Drug Administration | date = }}</ref> |
|
|
|
|
|
] has also been used in the formulation of ] such as ], ] and ]. |
|
|
|
|
|
* Prestium Pharma: Luxiq (betamethasone valerate) Foam, 0.12% <ref>{{cite web | title = Luxíq | work = Connetics Corporation | url = http://www.luxiq.com | archive-url = https://web.archive.org/web/20070303114823/http://www.luxiq.com/ | archive-date = 3 March 2007 }}</ref> is a mid-strength corticosteroid foam used primarily to treat psoriasis or other inflammatory conditions of the scalp. |
|
|
* Merck: Lotrisone (containing betamethasone dipropionate, ])<ref name="Lotrisone label">{{cite web | title=Lotrisone- clotrimazole and betamethasone dipropionate cream | work = DailyMed | publisher = U.S. National Library of Medicine | date=14 June 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=40ec029d-8af0-4f8f-bea1-1d38779ec232 | access-date=13 April 2020}}</ref> contains both a corticosteroid (betamethasone) and anti-fungal agent (clotrimazole) and is used to treat fungal infections that are also inflamed |
|
|
* Leo Pharma: Taclonex (containing betamethasone dipropionate, ])<ref>{{cite web | title = TACLONEX Highlights of Prescribing Information | work = LEO Laboratories Ltd. | url = http://www.taclonex.com/ }}</ref> is a combination of corticosteroid (betamethasone) and a vitamin D analogue (calcipotriene) and is used to treat frequent and persistent dermatatoses by reducing inflammation and promoting healing of the skin barrier. |
|
|
|
|
|
== Names == |
|
|
Brand names include Alphatrex, Beta-Val, Diprolene, Diprolene AF, Diprosalic (with ])<ref>{{cite book | vauthors = Weller RB, Hunter HJ, Mann MW | chapter = Formulary 1: Topical Treatments |title=Clinical Dermatology |date=27 January 2015 |publisher=John Wiley & Sons |isbn=978-0-470-65952-6 |page=402 | chapter-url = https://books.google.com/books?id=W69YBQAAQBAJ&dq=diprosalic+ointment&pg=PA402 |access-date=2 December 2022 |language=en}}</ref> Diprosone, Dovobet (LEO Pharma A/S),<ref>{{cite web | url=https://www.medicines.org.uk/emc/product/1609/smpc#gref | title=Dovobet Ointment - Summary of Product Characteristics (SMPC) | work = Electronic Medicines Compendium (EMC) | publisher = Datapharm Ltd. }}</ref> Eleuphrat and Luxiq.{{citation needed|date=April 2020}} |
|
|
|
|
|
] |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
== External links == |
|
|
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/betamethasone%20dipropionate | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Betamethasone dipropionate }} |
|
|
|
|
|
{{Glucocorticoids}} |
|
|
{{Glucocorticoidics}} |
|
|
{{Portal bar | Medicine}} |
|
|
|
|
|
{{DEFAULTSORT:Betamethasone Dipropionate}} |
|
|
] |
|
|
] |
|
|
] |