2812. Danazol

Nomenclature

CAS number: 17230-88-5
(17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol; 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol; 17α-ethynyl-17β-hydroxy-4-androsteno[2,3-d]isoxazole; Win-17757; Bonzol (Tokyo Tanabe); Cyclomen (Sanofi-Synthelabo); Danatrol (Sanofi-Synthelabo); Danocrine (Sanofi-Synthelabo); Danol (Sanofi-Synthelabo); Danoval (Krka); Ladogal (Sanofi-Synthelabo); Winobanin (Sanofi-Synthelabo).
C22H27NO2; mol wt 337.46.
C 78.30%, H 8.06%, N 4.15%, O 9.48%.

Description and references

Anterior pituitary supressant. Anabolic steroid deriv of ethisterone, q.v., with mild androgenic side effects (an impeded androgen). Prepn: GB 905844 (1962 to Sterling Drug), C.A. 58, 6895c (1963); Manson et al., J. Med. Chem. 6, 1 (1963); Clinton, Manson, US 3135743 (1964 to Sterling Drug). Activity studies: Sherins et al., J. Clin. Endocrinol. Metab. 32, 522 (1971); Dmowski et al., Fertil. Steril. 22, 9 (1971). Clinical studies in endometriosis and other endocrine disorders: R. B. Greenblatt et al., ibid. 102. Series of articles on pharmacology, pharmacokinetics and clinical use: Drugs 19, 321-372 (1980). Use in idiopathic thrombocytopenic purpura: Y. S. Ahn et al., N. Engl. J. Med. 308, 1396 (1983); in hemophilia: H. R. Gralnick et al., ibid. 1393.

Chemical structure

Properties

Crystals from acetone, mp 224.4-226.8°. [α]D25 +7.5° (ethanol); [α]D25 +21.9° (chloroform). uv max (ethanol): 286 nm (ε 11300).

Therapeutic Category

Antigonadotropin.

Keywords

Antigonadotropin