3627. Epostane

Nomenclature

CAS number: 80471-63-2
(4α,5α,17β)-4,5-Epoxy-3,17-dihydroxy-4,17-dimethylandrost-2-ene-2-carbonitrile; (2α,4α,5α,17β)-4,5-epoxy-17-hydroxy-4,17-dimethyl-3-oxoandrostane-2-carbonitrile; Win-32729.
C22H31NO3; mol wt 357.49.
C 73.91%, H 8.74%, N 3.92%, O 13.43%.

Description and references

3β-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).

Chemical structure

Properties

Crystals, mp 191-194° from DMF/H2O. [α]D25 +67.4° (c = 1 in pyridine).

Therapeutic Category

Interceptive.

Therapeutic Category (Veterinary)

Interceptive, labor inducer.

Keywords

Abortifacient/Interceptive