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'''Fluocinolone acetonide''' is a [[corticosteroid]] primarily used in [[dermatology]] to reduce skin inflammation and relieve itching.{{Citation needed|date=November 2019|reason=Please clarify which it is corticoid: gluco- or mineralo-}} It is a synthetic [[hydrocortisone]] 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 | doi = 10.1021/ja01498a041 }}</ref> Preparations containing it were first marketed under the name Synalar. A typical dosage strength used in dermatology is 0.01–0.025%. One such cream is sold under the brand name '''Flucort-N''' and includes the antibiotic [[neomycin]].
'''Fluocinolone acetonide''' is a [[corticosteroid]] primarily used in [[dermatology]] to reduce skin inflammation and relieve itching.{{Citation needed|date=November 2019|reason=Please clarify which it is corticoid: gluco- or mineralo-}} It is a synthetic [[hydrocortisone]] 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 name Synalar. A typical dosage strength used in dermatology is 0.01–0.025%. One such cream is sold under the brand name '''Flucort-N''' and includes the antibiotic [[neomycin]].


Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated [[chondrogenesis]] 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 was also found to strongly potentiate TGF-β-associated [[chondrogenesis]] 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 intravitreal implants have been used to treat non-infectious [[uveitis]]. A systematic review could not determine whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.<ref name="Brady">{{cite journal | vauthors = Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J | display-authors = 6 | title = Corticosteroid implants for chronic non-infectious uveitis | journal = The Cochrane Database of Systematic Reviews | volume = 2 | issue = 2 | pages = CD010469 | date = February 2016 | pmid = 26866343 | pmc = 5038923 | doi = 10.1002/14651858.CD010469.pub2 }}</ref> A fluocinolone acetonide intravitreal implant with the brand name '''Iluvien''' is sold by biopharmaceutical company [[Alimera Sciences]] to treat [[diabetic macular edema]] (DME).<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>
Fluocinolone acetonide intravitreal implants have been used to treat non-infectious [[uveitis]]. A systematic review could not determine whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.<ref name="Brady">{{cite journal | vauthors = Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J | display-authors = 6 | title = Corticosteroid implants for chronic non-infectious uveitis | journal = The Cochrane Database of Systematic Reviews | volume = 2016 | issue = 2 | pages = CD010469 | date = February 2016 | pmid = 26866343 | pmc = 5038923 | doi = 10.1002/14651858.CD010469.pub2 }}</ref> A fluocinolone acetonide intravitreal implant with the brand name '''Iluvien''' is sold by biopharmaceutical company [[Alimera Sciences]] to treat [[diabetic macular edema]] (DME).<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>


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Revision as of 17:23, 8 July 2023

Fluocinolone acetonide
Clinical data
Trade namesSynalar, Iluvien, others
AHFS/Drugs.comMonograph
Monograph
Pregnancy
category
  • AU: A
Routes of
administration		Topical, ophthalmic intravitreal injection
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver, CYP3A4-mediated
Elimination half-life1.3 to 1.7 hours
Identifiers
  • (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.607 Edit this at Wikidata
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.495 g·mol−1
3D model (JSmol)
  • O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
  • InChI=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 checkY
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching.[citation needed] It is a synthetic hydrocortisone 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.[2] Preparations containing it were first marketed under the name Synalar. A typical dosage strength used in dermatology is 0.01–0.025%. One such cream is sold under the brand name Flucort-N and includes the antibiotic neomycin.

Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated chondrogenesis 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.[3]

Fluocinolone acetonide intravitreal implants have been used to treat non-infectious uveitis. A systematic review could not determine whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.[4] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME).[5]

It was approved for medical use in 1961.[6]

Classification

Fluocinolone is a group V (0.025%) or group VI (0.01%) corticosteroid under US classification.

See also

References

  1. ^ "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
  2. ^ Mills JS, Bowers A, Djerassi C, Ringold HJ (1960). "Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide". Journal of the American Chemical Society. 80 (13): 3399–3404. doi:10.1021/ja01498a041.
  3. ^ Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, et al. (September 2015). "Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration". Journal of Bone and Mineral Research. 30 (9): 1585–1596. doi:10.1002/jbmr.2502. PMC 5569386. PMID 25753754.
  4. ^ Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, et al. (February 2016). "Corticosteroid implants for chronic non-infectious uveitis". The Cochrane Database of Systematic Reviews. 2016 (2): CD010469. doi:10.1002/14651858.CD010469.pub2. PMC 5038923. PMID 26866343.
  5. ^ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.
  6. ^ Fischer J, Ganellin CR, eds. (2006). "Tables of Structural and Functional Analogues: Systemic Hormonal Preparations". Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495.
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