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Revision as of 12:33, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456536921 of page Fluocinolone_acetonide for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 15:00, 5 September 2024 edit Citation bot (talk | contribs)Bots5,389,845 edits Removed parameters. | Use this bot. Report bugs. | Suggested by GoingBatty | Category:CS1 maint: PMC embargo expired | #UCB_Category 2/3 
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{{Short description|Corticosteroid anti-inflammatory drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Use dmy dates|date=July 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 396489512 | verifiedrevid = 461101531
⚫ | IUPAC_name = (1''S'',2''S'',4''R'',8''S'',9''S'',11''S'',12''R'',13''S'',19''S'')-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacycloicosa-14,17-dien-16-one
| image = Fluocinolone acetonide.svg | image = Fluocinolone acetonide.svg
| alt =
| image2 = Fluocinolone acetonide (Ball-n-Stick).png
| alt2 =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Synalar, others
| Drugs.com = {{drugs.com|international|fluocinolone-acetonide}} | Drugs.com = {{drugs.com|monograph|fluocinolone-topical}}<br />{{drugs.com|monograph|fluocinolone-acetonide-eent}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = A
⚫ | pregnancy_category =
| pregnancy_US = <!-- A / B / C / D / X -->
⚫ | routes_of_administration = Topical, ophthalmic intravitreal injection
⚫ | pregnancy_category = C
⚫ | ATC_prefix = C05
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
⚫ | ATC_suffix = AA10
| legal_UK = <!-- GSL / P / POM / CD -->
⚫ | ATC_supplemental = {{ATC|D07|AC04}} {{ATC|S01|BA15}} {{ATC|S02|BA08}}
⚫ | legal_US = <!-- OTC / Rx-only -->

⚫ | legal_status =
| legal_AU = S4
⚫ | routes_of_administration = Topical
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | url=https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00500 | title=Regulatory Decision Summary for Iluvien | work = Drug and Health Product Portal | publisher = Health Canada | date=23 October 2014 }}</ref>
| legal_UK = POM
⚫ | legal_US = Rx-only
⚫ | legal_status = Rx-only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = ], ]-mediated | metabolism = ], ]-mediated
| elimination_half-life = 1.3 to 1.7 hours | elimination_half-life = 1.3 to 1.7 hours
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 67-73-2 | CAS_number = 67-73-2
⚫ | ATC_prefix = C05
⚫ | ATC_suffix = AA10
⚫ | ATC_supplemental = {{ATC|D07|AC04}} {{ATC|S01|BA15}} {{ATC|S02|BA08}}
| PubChem = 6215 | PubChem = 6215
| IUPHAR_ligand = 7077
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00591 | DrugBank = DB00591
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0CD5FD6S2M | UNII = 0CD5FD6S2M
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01825 | KEGG = D01825
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 31623
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 989 | ChEMBL = 989


<!--Chemical data--> <!--Chemical data-->
⚫ | IUPAC_name = (1''S'',2''S'',4''R'',8''S'',9''S'',11''S'',12''R'',13''S'',19''S'')-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacycloicosa-14,17-dien-16-one
| C=24 | H=30 | F=2 | O=6 | C=24 | H=30 | F=2 | O=6
| molecular_weight = 452.488 g/mol
| smiles = O=C\1\C=C5/(/C=C/1)(C)2(F)(3(C2O)(4(OC(O4C3)(C)C)C(=O)CO)C)C5F | smiles = O=C\1\C=C5/(/C=C/1)(C)2(F)(3(C2O)(4(OC(O4C3)(C)C)C(=O)CO)C)C5F
| InChI = 1/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
| InChIKey = FEBLZLNTKCEFIT-VSXGLTOVBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1 | StdInChI = 1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
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| StdInChIKey = FEBLZLNTKCEFIT-VSXGLTOVSA-N | StdInChIKey = FEBLZLNTKCEFIT-VSXGLTOVSA-N
}} }}

'''Fluocinolone acetonide''' is a fluorinated ] primarily used in ] to reduce skin inflammation and relieve itching.<ref name="AHFS" /> It is a synthetic ] derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its activity. It was first synthesized in 1959 in the Research Department of Syntex Laboratories S.A. Mexico City.<ref>{{cite journal | vauthors = Mills JS, Bowers A, Djerassi C, Ringold HJ | title = Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide | journal = Journal of the American Chemical Society | volume = 80 | pages = 3399–3404 | date = 1960 | issue = 13 | doi = 10.1021/ja01498a041 }}</ref> Preparations containing it were first marketed under the brand name '''Synalar'''.

Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated ] of bone marrow mesenchymal stem/progenitor cells, by increasing the levels of collagen type II by more than 100 fold compared to the widely used dexamethasone.<ref name="pmid25753754">{{cite journal | vauthors = Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T | display-authors = 6 | title = Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration | journal = Journal of Bone and Mineral Research | volume = 30 | issue = 9 | pages = 1585–1596 | date = September 2015 | pmid = 25753754 | pmc = 5569386 | doi = 10.1002/jbmr.2502 }}</ref>

Fluocinolone acetonide ] have been used to treat non-infectious ]. A systematic review could not determine with any confidence whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.<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> A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company ] to treat ].<ref>{{cite web|url=https://www.healio.com/news/ophthalmology/20200702/realworld-study-shows-longterm-safety-efficacy-of-iluvien-in-dme |title=Real-world study shows long-term safety, efficacy of Iluvien in DME |website=Healio |date=2020-07-02 |access-date=2020-10-28}}</ref>

<!-- Society and culture -->
It was approved for medical use in 1961.<ref name=Fis2006>{{cite book | chapter = Tables of Structural and Functional Analogues: Systemic Hormonal Preparations | veditors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=485 | chapter-url = https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 |language=en}}</ref>

==Classification==
{{unreferenced section|date=July 2024}}
Fluocinolone is a group V (0.025%) or group VI (0.01%) ].

==Brand names ==
Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq,<ref>{{cite web | title=Yutiq- fluocinolone acetonide implant | website=DailyMed | date=16 October 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f270cad8-ed82-4969-b785-831a1910bfa6 | access-date=25 December 2023}}</ref> and others.<ref name="AHFS">{{cite web | title=Fluocinolone (Topical) Monograph for Professionals | website=Drugs.com | date=19 January 2024 | url=https://www.drugs.com/monograph/fluocinolone-topical.html | access-date=7 July 2024}}</ref><ref>{{cite web | title=Fluocinolone ophthalmic implant Uses, Side Effects & Warnings | website=Drugs.com | date=6 October 2023 | url=https://www.drugs.com/mtm/fluocinolone-ophthalmic-implant.html | access-date=7 July 2024}}</ref>

== References ==
{{reflist}}

{{Glucocorticoids}}
{{Vasoprotectives}}
{{Otologicals}}
{{Glucocorticoidics}}
{{Portal bar | Medicine}}
{{Authority control}}

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