Fluocinolone acetonide

Fluocinolone acetonide

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[10.8.0.0^2,9.0^4,8.0^13,18]icosa-14,17-dien-16-one
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	C
Routes of administration	Topical
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
ATC code	C05AA10 (WHO) D07AC04 S01BA15 S02BA08
PubChem	CID 6215
IUPHAR/BPS	7077
DrugBank	DB00591
ChemSpider	5980
UNII	0CD5FD6S2M
KEGG	D01825
ChEBI	CHEBI:31623
ChEMBL	CHEMBL989
Chemical data
Formula	C24H30F2O6
Molar mass	452.488 g/mol
SMILES 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 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 Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N
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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

• Topical steroid
• Fluocinonide
• Glucocorticoid

References

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.