4197. Flurandrenolide

Nomenclature

CAS number: 1524-88-5
(6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; 6α-fluoro-11β,16α,17,21-tetrahydroxypregn-4-ene-3,20-dione cyclic 16,17-acetal with acetone; 6α-fluoro-16α,17α-isopropylidenedioxy-4-pregnene-11β,21-diol-3,20-dione; 6α-fluoro-11β,16α,17,21-tetrahydroxyprogesterone cyclic 16,17-acetal with acetone; fludroxycortide; fluorandrenolone; flurandrenolone; flurandrenolone acetonide; Cordran (Watson); Drenison (Lilly); Drocort (Lilly); Sermaka (Lilly).
C24H33FO6; mol wt 436.51.
C 66.04%, H 7.62%, F 4.35%, O 21.99%.

Description and references

Prepn: H. J. Ringold et al., DE 1131213; eidem, US 3126375 (1962, 1964 both to Syntex). HPLC determn in pharmaceutical cream: R. Pearlman et al., Int. J. Pharm. 18, 53 (1984); in urine: E. Neufeld et al., J. Chromatogr. B 718, 273 (1998). Clinical trial in psoriasis: G. G. Krueger et al., J. Am. Acad. Dermatol. 38, 186 (1998).

Chemical structure

Properties

Crystals from acetone + hexane, mp 247-255°. [α]D +140-150° (CHCl3). uv max: 236 nm (log ε 4.17).

Therapeutic Category

Glucocorticoid; antipsoriatic.

Keywords

Glucocorticoid; Antipsoriatic