Danazol

Not to be confused with Danabol.
Danazol
Clinical data
Trade namesDanatrol, Danocrine, Danol, Danoval, others
Other namesWIN-17757; 2,3-Isoxazolethisterone; 2,3-Isoxazol-17α-ethynyltestosterone; 17α-Ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole
AHFS/Drugs.comMonograph
MedlinePlusa682599
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid; Progestogen; Progestin; Antigonadotropin; Steroidogenesis inhibitor; Antiestrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilitySaturable with dosage, higher with food intake[2]
Protein bindingTo albumin, SHBGTooltip sex hormone-binding globulin, CBGTooltip corticosteroid-binding globulin[3][4][5]
MetabolismLiver (CYP3A4)[9][6]
Metabolites• 2-OHM-Ethisterone[6]
• Ethisterone[7][8]
Elimination half-lifeAcute: 3–10 hours[9][2]
Chronic: 24–26 hours[9]
ExcretionUrine, feces[9][2]
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.037.503 Edit this at Wikidata
Chemical and physical data
FormulaC22H27NO2
Molar mass337.463 g·mol−1
3D model (JSmol)
  • C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C
  • 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 checkY
  • Key:POZRVZJJTULAOH-LHZXLZLDSA-N checkY
  (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.[9][2][10][11][12] It is taken by mouth.[2]

The use of danazol is limited by masculinizing side effects such as acne, excessive hair growth, and voice deepening.[2][13] 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.[5][14][15][16]

Danazol was discovered in 1963 and was introduced for medical use in 1971.[14][17][18][19] Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by gonadotropin-releasing hormone analogues (GnRH analogues) in the treatment of endometriosis.[4]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c d e f "Danocrine Brand of Danazol Capsules, USP" (PDF). Sanofi-Aventis U.S. LLC. U.S. Food and Drug Administration.
  3. ^ Griffin JP, D'Arcy PF (17 November 1997). A Manual of Adverse Drug Interactions. Elsevier. pp. 194–. ISBN 978-0-08-052583-9.
  4. ^ 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.
  5. ^ a b Cite error: The named reference ThomasRock2012 was invoked but never defined (see the help page).
  6. ^ a b Cite error: The named reference LemkeWilliams2012 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Dörwald2013 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Kurman2013 was invoked but never defined (see the help page).
  9. ^ a b c d e Brayfield A, ed. (30 October 2013). "Danazol". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 1 April 2014.
  10. ^ 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.
  11. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 293–. ISBN 978-3-88763-075-1.
  12. ^ 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.
  13. ^ 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.
  14. ^ a b Cite error: The named reference JonesRock2015 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Lupulescu1990 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference AltchekDeligdisch2003 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference NeumannPotts1979 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference EliasGwinup1983 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Dmowski1971 was invoked but never defined (see the help page).