Fluocinolone acetonide

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.

Fluocinolone acetonide

Clinical data
Trade names	Synalar, 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[1] 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 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]