Danazol

2875

IP/USP

Antigonadotropin

EDMF

[17230-88-5]

(17alpha)-Pregna-2,4-dien-20-yno[2,3- d ]is oxazol-17-ol

1-eth ynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a, 12a-dimethyl-1 H- cyclopenta[7,8]phenanthro[3,2- d ]isoxazol-1-ol; 17alpha-ethynyl-17beta-hydroxy-4-andro steno[2,3- d ] isoxazole

Win-17757

C 22 H 27 NO 2

337.46

C 78.30%, H 8.06%, N 4.15%, O 9.48%

Anterior pituitary supressant. Anabolic steroid deriv of ethisterone, q.v., with mild andro genic side effects (an impeded andro gen). Prepn: Brit. pat. 905,844 (1962 to Sterling Drug), C.A. 58, 6895c (1963); Manson et al., J. Med. Chem. 6, 1 (1963); Clinton, Manson, U.S. pat. 3,135,743 (1964 to Ster ling Drug). Activity studies: Sherins et al., J. Clin. Endo crinol. Metab. 32, 522 (1971); Dmowski et al., Fert. Steril. 22, 9 (1971). Clinical studies in endometriosis and other en docrine disorders: R. B. Greenblatt et al., ibid. 102. Series of articles on pharmacology, pharmacokinetics and clin ical use: Drugs 19, 321-372 (1980). Use in idiopathic throm bo cytopenic purpura: Y. S. Ahn et al., N. Engl. J. Med. 308, 1396 (1983); in hemophilia: H. R. Gralnick et al., ibid. 1393.

Crystals from acetone, mp 224.4-226.8degrees . [alpha] D 25 +7.5degrees (etha nol) ; [alpha] D 25 +21.9degrees (chloroform) . uv max (ethanol): 286 nm (epsi 11300) .

224.4-226.8

+7.5degrees; +21.9