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.^[8]^[1]^[9]^[10]^[11] It is taken by mouth.^[1]

The use of danazol is limited by masculinizing side effects such as acne, excessive hair growth, and voice deepening.^[1]^[12] 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.^[4]^[13]^[14]^[15]

Danazol was discovered in 1963 and was introduced for medical use in 1971.^[13]^[16]^[17]^[18] 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.^[3]

^ ^a ^b ^c ^d ^e ^f "Danocrine Brand of Danazol Capsules, USP" (PDF). Sanofi-Aventis U.S. LLC. U.S. Food and Drug Administration. Archived from the original (PDF) on March 14, 2016.
^ Griffin JP, D'Arcy PF (17 November 1997). A Manual of Adverse Drug Interactions. Elsevier. pp. 194–. ISBN 978-0-08-052583-9.
^ ^a ^b Nieschlag E, Behre HM, Nieschlag S (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 426–428. ISBN 978-3-540-78355-8.
^ ^a ^b Cite error: The named reference ThomasRock2012 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
^ Cite error: The named reference Dörwald2013 was invoked but never defined (see the help page).
^ Cite error: The named reference Kurman2013 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e Brayfield A, ed. (30 October 2013). "Danazol". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 1 April 2014.
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 345–. ISBN 978-1-4757-2085-3.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 293–. ISBN 978-3-88763-075-1.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 91–. ISBN 978-94-011-4439-1.
^ Selak V, Farquhar C, Prentice A, Singla A (October 2007). Farquhar C (ed.). "Danazol for pelvic pain associated with endometriosis". The Cochrane Database of Systematic Reviews (4): CD000068. doi:10.1002/14651858.CD000068.pub2. hdl:2292/28213. PMID 17943735.
^ ^a ^b Cite error: The named reference JonesRock2015 was invoked but never defined (see the help page).
^ Cite error: The named reference Lupulescu1990 was invoked but never defined (see the help page).
^ Cite error: The named reference AltchekDeligdisch2003 was invoked but never defined (see the help page).
^ Cite error: The named reference NeumannPotts1979 was invoked but never defined (see the help page).
^ Cite error: The named reference EliasGwinup1983 was invoked but never defined (see the help page).
^ Cite error: The named reference Dmowski1971 was invoked but never defined (see the help page).

[DanocrineLabel-1] ^ ^a ^b ^c ^d ^e ^f "Danocrine Brand of Danazol Capsules, USP" (PDF). Sanofi-Aventis U.S. LLC. U.S. Food and Drug Administration. Archived from the original (PDF) on March 14, 2016.

[GriffinD'Arcy1997-2] Griffin JP, D'Arcy PF (17 November 1997). A Manual of Adverse Drug Interactions. Elsevier. pp. 194–. ISBN 978-0-08-052583-9.

[NieschlagBehre2010-3] Nieschlag E, Behre HM, Nieschlag S (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 426–428. ISBN 978-3-540-78355-8.

[ThomasRock2012-4] Cite error: The named reference ThomasRock2012 was invoked but never defined (see the help page).

[LemkeWilliams2012-5] Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).

[Dörwald2013-6] Cite error: The named reference Dörwald2013 was invoked but never defined (see the help page).

[Kurman2013-7] Cite error: The named reference Kurman2013 was invoked but never defined (see the help page).

[Martindale2013-8] Brayfield A, ed. (30 October 2013). "Danazol". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 1 April 2014.

[Elks2014-9] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 345–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-10] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 293–. ISBN 978-3-88763-075-1.

[MortonHall2012-11] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 91–. ISBN 978-94-011-4439-1.

[Farquhar2007-12] Selak V, Farquhar C, Prentice A, Singla A (October 2007). Farquhar C (ed.). "Danazol for pelvic pain associated with endometriosis". The Cochrane Database of Systematic Reviews (4): CD000068. doi:10.1002/14651858.CD000068.pub2. hdl:2292/28213. PMID 17943735.

[JonesRock2015-13] Cite error: The named reference JonesRock2015 was invoked but never defined (see the help page).

[Lupulescu1990-14] Cite error: The named reference Lupulescu1990 was invoked but never defined (see the help page).

[AltchekDeligdisch2003-15] Cite error: The named reference AltchekDeligdisch2003 was invoked but never defined (see the help page).

[NeumannPotts1979-16] Cite error: The named reference NeumannPotts1979 was invoked but never defined (see the help page).

[EliasGwinup1983-17] Cite error: The named reference EliasGwinup1983 was invoked but never defined (see the help page).

[Dmowski1971-18] Cite error: The named reference Dmowski1971 was invoked but never defined (see the help page).

[1]

[2]

[3]

[4]

[8]

[5]

[6]

[7]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]

[17]

[18]