4151. Fluocinonide

Nomenclature

CAS number: 356-12-7
(6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; 6α,9-difluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone, 21-acetate; 21-acetoxy-6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione; 16α,17α-isopropylidene-6α-fluorotriamcinolone 21-acetate; fluocinolide (obsolete); fluocinolide acetate (obsolete); fluocinolone acetonide acetate; Biscosal (Ohta); Dermaplus (Ripari-Gero); Lidex (Syntex); Metosyn (Zeneca); Synalate (rescinded) (Syntex); Straderm (ITA); Topsym (Grünenthal); Topsymin (Grünenthal); Topsyne (Cassenne); Topsyn (Syntex).
C26H32F2O7; mol wt 494.52.
C 63.15%, H 6.52%, F 7.68%, O 22.65%.

Description and references

Prepn: GB 916996 (1963 to Olin Mathieson), C.A. 59, 1716b (1963); H. J. Ringold, G. Rosenkranz, US 3124571; H. J. Ringold et al., US 3126375 (both 1964 to Syntex); J. Fried, US 3197469 (1965 to Pharm. Res. Prod.). NMR: A. D. Cross, P. W. Landis, J. Am. Chem. Soc. 86, 4005 (1964).

Chemical structure

Properties

Crystals from methanol. mp 308-311°. [α]D +83° (chloroform). uv max: 237 nm (log ε 4.18).

Therapeutic Category

Anti-inflammatory; glucocorticoid.

Keywords

Glucocorticoid