Title: Epostane
CAS Registry Number: 80471-63-2
CAS Name: (4a,5a,17b)-4,5-Epoxy-3,17-dihydroxy-4,17-dimethylandrost-2-ene-2-carbonitrile
Additional Names: (2a,4a,5a,17b)-4,5-epoxy-17-hydroxy-4,17-dimethyl-3-oxoandrostane-2-carbonitrile
Manufacturers' Codes: Win-32729
Molecular Formula: C22H31NO3
Molecular Weight: 357.49
Percent Composition: C 73.91%, H 8.74%, N 3.92%, O 13.43%
Literature References: 3b-Hydroxysteroid dehydrogenase inhibitor; derivative of trilostane, q.v. Prepn as ketone tautomer: R. G. Christiansen, DE 2855091; idem, US 4160027 (both 1979 to Sterling). Pharmacology and interceptive activity: J. E. Creange et al., Contraception 24, 289 (1981); R. G. Christiansen et al., J. Med. Chem. 27, 928 (1984). Clinical pharmacology: Z. M. Van der Spuy et al., Clin. Endocrinol. 19, 521 (1983); N. S. Pattison et al., Fertil. Steril. 42, 875 (1984). Clinical evaluation as abortifacient: L. Birgerson et al., Contraception 35, 111 (1987); M. J. Crooij et al., N. Engl. J. Med. 319, 813 (1988). Comparative clinical study with mifepristone, q.v., as abortifacient: L. Birgerson, V. Odlind, Fertil. Steril. 48, 565 (1987). Induction of labor in swine: P. A. Martin et al., J. Anim. Sci. 64, 497 (1987); in sheep: M. Silver, Vet. Rec. 120, 299 (1987). Regulation of ovulation in sheep: R. Webb, J. Reprod. Fertil. 79, 231 (1987). Abortifacient efficacy in dogs: D. M. Keister et al., Theriogenology 30, 497 (1988).
Properties: Crystals, mp 191-194° from DMF/H2O. [a]D25 +67.4° (c = 1 in pyridine).
Melting point: mp 191-194°
Optical Rotation: [a]D25 +67.4° (c = 1 in pyridine)
Therap-Cat: Interceptive.
Therap-Cat-Vet: Interceptive, labor inducer.
Keywords: Abortifacient/Interceptive. |