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Wikipedia

Fluocinolone acetonide

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
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
  • 67-73-2 Y
PubChem CID
  • 6215
IUPHAR/BPS
  • 7077
DrugBank
  • DB00591 Y
ChemSpider
  • 5980 Y
UNII
  • 0CD5FD6S2M
KEGG
  • D01825 Y
ChEBI
  • CHEBI:31623 N
ChEMBL
  • ChEMBL989 Y
CompTox Dashboard (EPA)
  • DTXSID0040674
ECHA InfoCard100.000.607
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.495 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Y
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Y
 NY (what is this?)  (verify)

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 with any confidence 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 edit

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

Society and culture edit

Brand names edit

Yutiq.[7]

References edit

  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. ^ Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG (August 2023). "Corticosteroid implants for chronic non-infectious uveitis". The Cochrane Database of Systematic Reviews. 2023 (8): CD010469. doi:10.1002/14651858.CD010469.pub4. PMC 10464657. PMID 37642198.
  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.
  7. ^ "Yutiq- fluocinolone acetonide implant". DailyMed. 16 October 2023. Retrieved 25 December 2023.

fluocinolone, acetonide, corticosteroid, primarily, used, dermatology, reduce, skin, inflammation, relieve, itching, citation, needed, synthetic, hydrocortisone, derivative, fluorine, substitution, position, steroid, nucleus, greatly, enhances, activity, first. 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 acetonideClinical dataTrade namesSynalar Iluvien othersAHFS Drugs comMonograph MonographPregnancycategoryAU ARoutes ofadministrationTopical ophthalmic intravitreal injectionATC codeC05AA10 WHO D07AC04 WHO S01BA15 WHO S02BA08 WHO Legal statusLegal statusAU S4 Prescription only CA only 1 UK POM Prescription only US only In general Prescription only Pharmacokinetic dataMetabolismLiver CYP3A4 mediatedElimination half life1 3 to 1 7 hoursIdentifiersIUPAC name 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 oneCAS Number67 73 2 YPubChem CID6215IUPHAR BPS7077DrugBankDB00591 YChemSpider5980 YUNII0CD5FD6S2MKEGGD01825 YChEBICHEBI 31623 NChEMBLChEMBL989 YCompTox Dashboard EPA DTXSID0040674ECHA InfoCard100 000 607Chemical and physical dataFormulaC 24H 30F 2O 6Molar mass452 495 g mol 13D model JSmol Interactive imageSMILES 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 5FInChI 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 YKey FEBLZLNTKCEFIT VSXGLTOVSA N Y N Y what is this verify Fluocinolone acetonide was also found to strongly potentiate TGF b 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 with any confidence 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 Contents 1 Classification 2 Society and culture 2 1 Brand names 3 ReferencesClassification editFluocinolone is a group V 0 025 or group VI 0 01 corticosteroid under US classification Society and culture editBrand names edit Yutiq 7 References edit Regulatory Decision Summary for Iluvien Drug and Health Product Portal Health Canada 23 October 2014 Mills JS Bowers A Djerassi C Ringold HJ 1960 Steroids CXXXVII Synthesis of a New Class of Potent Cortical Hormones 6a 9a Difluoro 16a Hydroxyprednisolone and its Acetonide Journal of the American Chemical Society 80 13 3399 3404 doi 10 1021 ja01498a041 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 b3 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 Reddy A Liu SH Brady CJ Sieving PC Palestine AG August 2023 Corticosteroid implants for chronic non infectious uveitis The Cochrane Database of Systematic Reviews 2023 8 CD010469 doi 10 1002 14651858 CD010469 pub4 PMC 10464657 PMID 37642198 Real world study shows long term safety efficacy of Iluvien in DME Healio 2020 07 02 Retrieved 2020 10 28 Fischer J Ganellin CR eds 2006 Tables of Structural and Functional Analogues Systemic Hormonal Preparations Analogue based Drug Discovery John Wiley amp Sons p 485 ISBN 9783527607495 Yutiq fluocinolone acetonide implant DailyMed 16 October 2023 Retrieved 25 December 2023 Portal nbsp Medicine nbsp This drug article relating to the cardiovascular system is a stub You can help Wikipedia by expanding it vte nbsp This dermatologic drug article is a stub You can help Wikipedia by expanding it vte nbsp This ophthalmology article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Fluocinolone acetonide amp oldid 1191725477, wikipedia, wiki, book, books, library,

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