Fluocinolone acetonide

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Fluocinolone acetonide
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
Systematic (IUPAC) 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-one
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • C
Routes of
administration
Topical
Legal status
Legal status
  • Prescription Only
Pharmacokinetic data
Metabolism Hepatic, CYP3A4-mediated
Biological half-life 1.3 to 1.7 hours
Identifiers
CAS Number 67-73-2 YesY
ATC code C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
PubChem CID 6215
IUPHAR/BPS 7077
DrugBank DB00591 YesY
ChemSpider 5980 YesY
UNII 0CD5FD6S2M YesY
KEGG D01825 YesY
ChEBI CHEBI:31623 N
ChEMBL CHEMBL989 YesY
Chemical data
Formula C24H30F2O6
Molar mass 452.488 g/mol
 NYesY (what is this?)  (verify)

Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. 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.[1] 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.[2]

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.[3]

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

See also[edit]

References[edit]

  1. ^ J S Mills, A. Bowers, Carl Djerassi and H.J. Ringold, 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, 3399-3404 (1960)
  2. ^ Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T. Fluocinolone Acetonide is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration. J Bone Miner Res. 2015. http://onlinelibrary.wiley.com/doi/10.1002/jbmr.2502/abstract
  3. ^ Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J (2016). "Corticosteroid implants for chronic non-infectious uveitis". Cochrane Database Syst Rev 2: CD010469. doi:10.1002/14651858.CD010469.pub2. PMID 26866343.