3140. Diflorasone
Nomenclature
CAS number: 2557-49-5
(6α,11β,16β)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 6α,9α-difluoro-16β-methyl-Δ1,4-pregnadiene-11β,17α,21-triol-3,20-dione; 6α,9α-difluoro-16β-methylprednisolone. C22H28F2O5; mol wt 410.45.
C 64.38%, H 6.88%, F 9.26%, O 19.49%.
Description and references
The 16β-analog of flumethasone, q.v. Prepn of free alcohol and 21-acetate: GB 881334 (1961 to Pfizer), C.A. 56, 15586c (1962); GB 898293; F. H. Lincoln et al., US 3557158 (1962, 1971 both to Upjohn); GB 912015 (1962 to Merck & Co.). Prepn of the 17,21-diacetate: D. E. Ayer et al., DE 2308731; eidem, US 3980778 (1973, 1976 both to Upjohn). Proposed mechanism of action: S. Hammarstrom et al., Science 197, 994 (1977). Pharmacology: S. Wickrema et al., J. Invest. Dermatol. 71, 372 (1978). Clinical study: S. M. Bluefarb et al., J. Int. Med. Res. 4, 454 (1976).
Derivative
Diacetate.Nomenclature
CAS number: 33564-31-7
U-34865; Dermaflor (Brocchieri); Diacort (Pfizer); Florone (Pfizer); Maxiflor (Allergan); Psorcon (Dermik); Soriflor (Nycomed). C26H32F2O7; mol wt 494.52.
C 63.15%, H 6.52%, F 7.68%, O 22.65%.
Properties
Crystals from ethyl acetate-Skellysolve C and acetone-methanol, mp 221-223° (dec). uv max (alc): 238 nm (ε 17250). [α]D +61° (chloroform).Therapeutic Category
Anti-inflammatory (topical); glucocorticoid.
Keywords
Glucocorticoid