danazol

Also known as Danocrine®, Cyclomen, Danazolum

Danazol, sold as Danocrine and other brand names, is an oral medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions.

Chemical data

Formula: C22H27NO2
Molecular weight: 337.5 g/mol
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
SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N
XLogP: 3.8
Polar surface area: 46.3 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

3,337 papers

Danazol.Annals of internal medicine · 1982
Danazol.The American journal of medicine · 1989
Danazol and plasma lipoprotein metabolism.International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics · 1995
Danazol: endocrine pharmacology and therapeutic applications.American journal of obstetrics and gynecology · 1981
Danazol for unexplained infertilty.The Cochrane database of systematic reviews · 2000

via PubMed

Wikidata facts

Mass: 337.204179

Show 6 more facts

chemical formula: C₂₂H₂₇NO₂
World Health Organisation international non-proprietary name: danazol
isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
canonical SMILES: CC12CCC3C(C1CCC2(C#C)O)CCC4=CC5=C(CC34C)C=NO5
defined daily dose: 0.6
Commons category: Danazol

Sources (7)

via Wikidata · CC0

~17 min read

Article

22 sections

Contents

Medical uses
Available forms
Contraindications
Side effects
Pharmacology
Pharmacodynamics
Modulation of steroid hormone receptors
Inhibition of steroidogenesis enzymes
Occupation and downregulation of carrier proteins
Antigonadotropic activity
Mechanism of action in endometriosis
Effects in men
Pharmacokinetics
Chemistry
History
Society and culture
Generic names
Brand names
Availability
Research
References
Further reading

Danazol, sold as Danocrine and other brand names, is an oral medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions.

The use of danazol is limited by masculinizing side effects such as acne, excessive hair growth, and voice deepening. Danazol has a complex mechanism of action, and is characterized as a weak androgen and anabolic steroid, a weak progestogen, a weak antigonadotropin, a weak steroidogenesis inhibitor, and a functional antiestrogen.