4152. Fluocortin Butyl
Nomenclature
CAS number: 41767-29-7
(6α,11β,16α)-6-Fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-oic
acid butyl ester; butyl 6α-fluoro-11β-hydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-oate; SH K 203; Varlane (Schering AG); Vaspit (Schering AG). C26H35FO5; mol wt 446.55.
C 69.93%, H 7.90%, F 4.25%, O 17.91%.
Description and references
The butyl ester deriv of fluocortolone-21-acid, a metabolite of fluocortolone, q.v., in humans. Prepn: H. Laurent et al., DE 2150268, DE 2150270; eidem, US 3824260 (1973, 1973, 1974, all to Schering AG); H. Laurent et al., Angew. Chem. 87, 70 (1975). Description of this new corticoid structure type, the pregnan-21-oic esters, their activity and methods for synthesis: H. Laurent et al., J. Steroid Biochem. 6, 185 (1975). Toxicity data: P. Günzel et al., Arzneim.-Forsch. 27, 2217 (1977). Series of articles on synthesis, pharmacology and clinical trials: ibid. 2185-2246.
Properties
Crystals from acetone/hexane, mp 195.1°. [α]D25 +136° (c = 0.5 in chloroform). uv max (methanol): 242 nm (ε 16800). Soluble in chloroform, ethanol; poorly sol in ethyl ether. Insol in water. LD50 in mice, rats (g/kg): >4 orally and s.c. (Günzel).Therapeutic Category
Anti-inflammatory.
Keywords
Glucocorticoid