Danazol

Danazol
Clinical data
Trade names	Danatrol, Danocrine, Danol, Danoval, others
Other names	WIN-17757; 2,3-Isoxazolethisterone; 2,3-Isoxazol-17α-ethynyltestosterone; 17α-Ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole
AHFS/Drugs.com	Monograph
MedlinePlus	a682599
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Androgen; Anabolic steroid; Progestogen; Progestin; Antigonadotropin; Steroidogenesis inhibitor; Antiestrogen
ATC code	G03XA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	Saturable with dosage, higher with food intake
Protein binding	To albumin, SHBGTooltip sex hormone-binding globulin, CBGTooltip corticosteroid-binding globulin
Metabolism	Liver (CYP3A4)
Metabolites	• 2-OHM-Ethisterone; • Ethisterone
Elimination half-life	Acute: 3–10 hours; Chronic: 24–26 hours
Excretion	Urine, feces
Identifiers
	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;
CAS Number	17230-88-5 ;
PubChem CID	28417;
IUPHAR/BPS	6942;
DrugBank	DB01406 ;
ChemSpider	26436 ;
UNII	N29QWW3BUO;
KEGG	D00289 ;
ChEBI	CHEBI:4315 ;
ChEMBL	ChEMBL1479 ;
CompTox Dashboard (EPA)	DTXSID2022880 ;
ECHA InfoCard	100.037.503
Chemical and physical data
Formula	C22H27NO2
Molar mass	337.463 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C;
	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 ; Key:POZRVZJJTULAOH-LHZXLZLDSA-N ;
	(verify)

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Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by gonadotropin-releasing hormone analogues (GnRH analogues) in the treatment of endometriosis.