CHEBI:4315 - danazol

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ChEBI Name danazol
ChEBI ID CHEBI:4315
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:505364, CHEBI:554019
Supplier Information ChemicalBook:CB9463336, eMolecules:30512482, eMolecules:2726153, ZINC000003881958
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Danazol, sold as Danocrine and other brand names, is a medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions. It is taken by mouth. 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. Danazol was discovered in 1963 and was introduced for medical use in 1971. Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by gonadotropin-releasing hormone analogues (GnRH analogues) in the treatment of endometriosis.
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Formula C22H27NO2
Net Charge 0
Average Mass 337.45532
Monoisotopic Mass 337.20418
InChI InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
InChIKey POZRVZJJTULAOH-LHZXLZLDSA-N
SMILES [H][C@@]12CCC3=Cc4oncc4C[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@@]1(O)C#C
Roles Classification
Biological Role(s): estrogen antagonist
A compound which inhibits or antagonises the biosynthesis or actions of estrogens.
Application(s): anti-estrogen
A drug which acts to reduce estrogenic activity in the body, either by reducing the amount of estrogen or by reducing the activity of whatever estrogen is present.
estrogen antagonist
A compound which inhibits or antagonises the biosynthesis or actions of estrogens.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing danazol (CHEBI:4315) has parent hydride pregnane (CHEBI:8386)
danazol (CHEBI:4315) has role anti-estrogen (CHEBI:50751)
danazol (CHEBI:4315) has role estrogen antagonist (CHEBI:50837)
danazol (CHEBI:4315) has role geroprotector (CHEBI:176497)
danazol (CHEBI:4315) is a 17β-hydroxy steroid (CHEBI:35343)
danazol (CHEBI:4315) is a terminal acetylenic compound (CHEBI:73477)
IUPAC Name
[1,2]oxazolo[4',5':2,3]-17α-pregn-4-en-20-yn-17-ol
INNs Sources
danazol KEGG DRUG
danazolum ChemIDplus
Brand Names Sources
Cyclomen DrugBank
Danocrine DrugBank
Manual Xrefs Databases
26436 ChemSpider
779 DrugCentral
D00289 KEGG DRUG
Danazol Wikipedia
DB01406 DrugBank
GB905844 Patent
US3135743 Patent
View more database links
Registry Numbers Types Sources
17230-88-5 CAS Registry Number ChemIDplus
4851114 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17929794 PubMed citation ChEMBL
18834112 PubMed citation ChEMBL
24134630 PubMed citation Europe PMC
27626530 PubMed citation Europe PMC
34462405 PubMed citation Europe PMC
Last Modified
26 October 2021