2774. Cyproterone
Nomenclature
CAS number: 2098-66-0
(1β,2β)-6-Chloro-1,2-dihydro-17-hydroxy-3′H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; 6-chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione; 6-chloro-6-dehydro-17α-hydroxy-1,2α-methyleneprogesterone; 6-chloro-1,2α-methylene-4,6-pregnadien-17α-ol-3,20-dione; SH-881; SH-80881. C22H27ClO3; mol wt 374.90.
C 70.48%, H 7.26%, Cl 9.46%, O 12.80%.
Description and references
Prepn of free alcohol: Wiechert, Neumann, DE 1189991 C.A. 63, 1842e (1965); Wiechert, US 3234093 (1965, 1966 both to Schering AG). Biodynamics in man: Gerhards et al., Arzneim.-Forsch. 23, 1550 (1973). The free alcohol is an anti-androgen; the acetate is both an anti-androgen and a progestogen. Effect on hormone secretion and on spermatogenesis in man: L. Moltz et al., Contraception 21, 393 (1980). Review of pharmacology and clinical studies (acetate) on acne and hirsutism in women: J. Hammerstein et al., J. Steroid Biochem. 19, 591 (1983).
Properties
Crystals from ethyl acetate, mp 237.5-240°.Derivative
Acetate.Nomenclature
CAS number: 427-51-0
CPA; SH-714; Androcur (Schering AG); Cyprostat (Schering AG). C24H29ClO4; mol wt 416.94.
C 69.14%, H 7.01%, Cl 8.50%, O 15.35%.
Properties
Crystals from diisopropyl ether, mp 200-201°. uv max (methanol): 281 nm (ε 17280).Derivative
Mixture of acetate with ethinyl estradiol.Nomenclature
Diane 35 (Schering AG); Dianette (Schering AG).Therapeutic Category
The acetate as antiandrogen; combination with estrogen in treatment of acne.
Keywords
Antiacne; Antiandrogen