Substance
ID:1222
Names and Identifiers
IUPAC Traditional name
danazol
IUPAC name
(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol
Synonyms
Danazol
Brand Name
DanocrineChronogynAnatrolCyclomen
Properties
Physical Property
Hydrophobicity(logP)
0.51 [PERRISSOUD,D & TESTA,B (1986)]
Molecule Details
Drug Groups
approved
Description
A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]
Indication
For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.
Pharmacology
Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.
Half Life
Approximately 24 hours.
References
•
Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5.
[Pubmed]
•
Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N.
[Pubmed]
•
Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8.
[Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. Pubmed
• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. Pubmed
• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. Pubmed