Title: Oxendolone
CAS Registry Number: 33765-68-3
CAS Name: (16b,17b)-16-Ethyl-17-hydroxyestr-4-en-3-one
Additional Names: 16b-ethyl-19-nortestosterone
Manufacturers' Codes: TSAA-291
Trademarks: Prostetin (Takeda)
Molecular Formula: C20H30O2
Molecular Weight: 302.45
Percent Composition: C 79.42%, H 10.00%, O 10.58%
Literature References: Prepn: K. Hiraga et al., DE 2100319; eidem, US 3856829 (1971, 1974 both to Takeda); K. Yoshioka et al., Chem. Pharm. Bull. 23, 3203 (1975). Stereoselective synthesis and NMR study: G. Goto et al., ibid. 25, 1295 (1977). Synthesis and anti-androgenic activity: eidem, ibid. 26, 1718 (1978). Physico-chemical properties and stabilities: K. Itakura et al., Takeda Kenkyushoho 37, 297 (1978), C.A. 91, 20879 (1979). Disposition and metabolism: S. Tanayama et al., Steroids 33, 65 (1979). Series of articles on pharmacology, mechanism of action, anti-androgen effects: Acta Endocrinol. 92 (Suppl 2), 1-107 (1979).
Properties: Crystals from ether, mp 152-153°. [a]D +41° (c = 1.0 in ethanol). uv max (ethanol): 240 nm (e 15800). Stable against heat, humidity, indoor light. Converted to the 16a- and 17a-epimers in sunlight. LD50 in rats, mice (g/kg): >10 orally; 5-10 i.m. and i.p. (Hiraga, 1971).
Melting point: mp 152-153°
Optical Rotation: [a]D +41° (c = 1.0 in ethanol)
Absorption maximum: uv max (ethanol): 240 nm (e 15800)
Toxicity data: LD50 in rats, mice (g/kg): >10 orally; 5-10 i.m. and i.p. (Hiraga, 1971)
Therap-Cat: Anti-androgen; in treatment of benign prostatic hypertrophy.
Keywords: Antiandrogen; Antiprostatic Hypertrophy. |