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[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	C
Legal status	Prescription Only
Routes of administration	Topical
Pharmacokinetic data
Metabolism	Hepatic, CYP3A4-mediated
Half-life	1.3 to 1.7 hours
Identifiers
CAS Registry Number	67-73-2 Y
ATC code	C05AA10 D07AC04 S01BA15 S02BA08
PubChem	CID 6215
DrugBank	DB00591 Y
ChemSpider	5980 Y
UNII	0CD5FD6S2M Y
KEGG	D01825 Y
ChEBI	CHEBI:31623 N
ChEMBL	CHEMBL989 Y
Chemical data
Formula	C24H30F2O6
Molecular 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  Y Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N  Y
N (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]

Flucinolone is a group IV (0.01-0.2%) or group V (0.025%) corticosteroid under US classification.

See also

• Topical steroid
• Fluocinonide
• Glucocorticoid

References