Danazol

Title: Danazol
CAS Registry Number: 17230-88-5
CAS Name: (17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol
Additional Names: 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; 17a-ethynyl-17b-hydroxy-4-androsteno[2,3-d]isoxazole
Manufacturers' Codes: Win-17757
Trademarks: Bonzol (Tokyo Tanabe); Cyclomen (Sanofi-Synthelabo); Danatrol (Sanofi-Synthelabo); Danocrine (Sanofi-Synthelabo); Danol (Sanofi-Synthelabo); Danoval (Krka); Ladogal (Sanofi-Synthelabo); Winobanin (Sanofi-Synthelabo)
Molecular Formula: C22H27NO2
Molecular Weight: 337.46
Percent Composition: C 78.30%, H 8.06%, N 4.15%, O 9.48%
Literature 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.
Properties: Crystals from acetone, mp 224.4-226.8°. [a]D25 +7.5° (ethanol); [a]D25 +21.9° (chloroform). uv max (ethanol): 286 nm (e 11300).
Melting point: mp 224.4-226.8°
Optical Rotation: [a]D25 +7.5° (ethanol); [a]D25 +21.9° (chloroform)
Absorption maximum: uv max (ethanol): 286 nm (e 11300)
Therap-Cat: Antigonadotropin.
Keywords: Antigonadotropin.
Danofloxacin Dansyl Chloride Danthron Dantrolene Daphnetin

Danazol
Danazol.svg
Systematic (IUPAC) name
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682599
Pregnancy cat. D (AU) X (US)
Legal status Prescription Only (S4) (AU) -only (US)
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Half-life 15 hours
Identifiers
CAS number 17230-88-5 YesY
ATC code G03XA01
PubChem CID 28417
DrugBank DB01406
ChemSpider 26436 YesY
UNII N29QWW3BUO YesY
KEGG D00289 YesY
ChEBI CHEBI:4315 YesY
ChEMBL CHEMBL1479 YesY
Synonyms 17β-hydroxy-2,4,17α-pregnadien-20-yno[2,3-D]isoxazole
Chemical data
Formula C22H27NO2 
Mol. mass 337.5 g/mol
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Danazol is a derivative of the synthetic steroid ethisterone, a modified progestogen, also known as 17-alpha-ethinyl testosterone. Before becoming available as a generic drug, danazol was marketed as Danocrine in the United States. It was approved by the US Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis in the early 1970s.[1] Although effective for endometriosis, its use is limited by its masculinizing side-effects.[2] Its role as a treatment for endometriosis has been largely replaced by the GnRH agonists.