Cyproterone
Title: Cyproterone
CAS Registry Number: 2098-66-0
CAS Name: (1b,2b)-6-Chloro-1,2-dihydro-17-hydroxy-3¢H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
Additional Names: 6-chloro-17-hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione; 6-chloro-6-dehydro-17a-hydroxy-1,2a-methyleneprogesterone; 6-chloro-1,2a-methylene-4,6-pregnadien-17a-ol-3,20-dione
Manufacturers' Codes: SH-881; SH-80881
Molecular Formula: C22H27ClO3
Molecular Weight: 374.90
Percent Composition: C 70.48%, H 7.26%, Cl 9.46%, O 12.80%
Literature 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°.
Melting point: mp 237.5-240°
 
Derivative Type: Acetate
CAS Registry Number: 427-51-0
Additional Names: CPA
Manufacturers' Codes: SH-714
Trademarks: Androcur (Schering AG); Cyprostat (Schering AG)
Molecular Formula: C24H29ClO4
Molecular Weight: 416.94
Percent Composition: 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 (e 17280).
Melting point: mp 200-201°
Absorption maximum: uv max (methanol): 281 nm (e 17280)
 
Derivative Type: Mixture of acetate with ethinyl estradiol
Trademarks: Diane 35 (Schering AG); Dianette (Schering AG)
 
Therap-Cat: The acetate as antiandrogen; combination with estrogen in treatment of acne.
Keywords: Antiacne; Antiandrogen.

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