Fluocinolone acetonide

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Fluocinolone acetonide
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
Clinical data
Trade names Synalar, others
AHFS/Drugs.com Monograph
Monograph
Pregnancy
category
  • AU:A
Routes of
administration 		Topical, ophthalmic intravitreal injection
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, CYP3A4-mediated
Elimination half-life 1.3 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 InfoCard 100.000.607 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H30F2O6
Molar mass 452.495 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 Yes check.svgY
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Fluocinolone acetonide is a fluorinated corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. [2] 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. [3] Preparations containing it were first marketed under the brand name Synalar.

Contents

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. [4]

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. [5] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema. [6]

It was approved for medical use in 1961. [7]

Classification

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

Brand names

Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq, [8] and others. [2] [9]

References

  1. ↑ "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
  2. 1 2 "Fluocinolone (Topical) Monograph for Professionals". Drugs.com. 19 January 2024. Retrieved 7 July 2024.
  3. ↑ 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. Bibcode:1960JAChS..82.3399M. doi:10.1021/ja01498a041.
  4. ↑ 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.{{cite journal}}: CS1 maint: overridden setting (link)
  5. ↑ 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.
  6. ↑ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2 July 2020. Retrieved 28 October 2020.
  7. ↑ 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   978-3-527-60749-5.
  8. ↑ "Yutiq- fluocinolone acetonide implant". DailyMed. 16 October 2023. Retrieved 25 December 2023.
  9. ↑ "Fluocinolone ophthalmic implant Uses, Side Effects & Warnings". Drugs.com. 6 October 2023. Retrieved 7 July 2024.
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