Fluocinolone acetonide

Fluocinolone acetonide

Clinical data
Trade names	Synalar, Iluvien, others
AHFS/Drugs.com	Monograph Monograph
Pregnancy category	AU: A
Routes of administration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Liver, CYP3A4-mediated
Elimination half-life	1.3 to 1.7 hours
Identifiers
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
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 InfoCard	100.000.607
Chemical and physical data
Formula	C24H30F2O6
Molar mass	452.495 g·mol−1
3D model (JSmol)	Interactive image
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 Y Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Y
NY (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. 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.

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. A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME).

It was approved for medical use in 1961.

Classification

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

See also

• Topical steroid
• Fluocinonide
• Ciprocinonide
• Glucocorticoid

External links

• "Fluocinolone acetonide". Drug Information Portal. U.S. National Library of Medicine.