User:Mr. Ibrahem/Danazol

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Not to be confused with Danabol.
Mr. Ibrahem/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 and anabolic steroid
Legal status
Legal status
Pharmacokinetic data
BioavailabilitySaturable with dosage, higher with food intake[1]
Protein bindingTo albumin, SHBGTooltip sex hormone-binding globulin, CBGTooltip corticosteroid-binding globulin[2][3][4]
MetabolismLiver (CYP3A4)[8][5]
Metabolites• 2-OHM-Ethisterone[5]
• Ethisterone[6][7]
Elimination half-lifeAcute: 3–10 hours[8][1]
Chronic: 24–26 hours[8]
ExcretionUrine, feces[8][1]
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
Chemical and physical data
FormulaC22H27NO2
Molar mass337.463 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC5=C(C[C@]34C)C=NO5
  • 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 under the brand name Danocrine among others, is a medication used to treat endometriosis, fibrocystic breast disease, and hereditary angioedema.[9] Due to less side effects, gonadotropin-releasing hormone analogues (GnRH analogues) are generally recommended over danazol in endometriosis.[3] It is not effective for precocious puberty.[11] It is taken by mouth.[9]

Side effects may include weight gain, acne, unwanted hair growth, and voice deepening.[3][10] Other side effects may include blood clots, liver problems, aggression, and idiopathic intracranial hypertension.[11] Use in pregnancy may harm the baby.[11] It decreases the production of sex steroids.[11] It has weak androgen and anabolic steroid effects; but no progestogen or estrogen effects.[11]

Danazol was first made in 1963 and was introduced for medical use in 1971.[12][13] It is available as a generic medication.[14] In the United States 60 pills of 200 mg cost about 115 USD as of 2021.[14] In the United Kingdom it is only available by special order.[9]

References[edit]

  1. ^ a b c "Archive copy" (PDF). Archived (PDF) from the original on 2021-04-02. Retrieved 2020-12-26.{{cite web}}: CS1 maint: archived copy as title (link)
  2. ^ J.P. Griffin; P.F. D'Arcy (17 November 1997). A Manual of Adverse Drug Interactions. Elsevier. pp. 194–. ISBN 978-0-08-052583-9. Archived from the original on 28 August 2021. Retrieved 26 December 2020.
  3. ^ a b c d Eberhard Nieschlag; Hermann M. Behre; Susan Nieschlag (13 January 2010). Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. pp. 426–428. ISBN 978-3-540-78355-8.
  4. ^ Eric J. Thomas; John Rock (6 December 2012). Modern Approaches to Endometriosis. Springer Science & Business Media. pp. 239–256. ISBN 978-94-011-3864-2. Archived from the original on 10 January 2020. Retrieved 26 December 2020.
  5. ^ a b Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1361–. ISBN 978-1-60913-345-0. Archived from the original on 10 January 2020. Retrieved 26 December 2020.
  6. ^ Florencio Zaragoza Dörwald (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 485–. ISBN 978-3-527-64565-7. Archived from the original on 9 January 2020. Retrieved 26 December 2020.
  7. ^ Robert J. Kurman (17 April 2013). Blaustein's Pathology of the Female Genital Tract. Springer Science & Business Media. pp. 390–. ISBN 978-1-4757-3889-6. Archived from the original on 10 January 2020. Retrieved 26 December 2020.
  8. ^ a b c d Brayfield, A, ed. (30 October 2013). "Danazol". Martindale: The Complete Drug Reference. Pharmaceutical Press. Archived from the original on 28 August 2021. Retrieved 1 April 2014.
  9. ^ a b c d BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 784. ISBN 978-0857114105.
  10. ^ a b Selak V, Farquhar C, Prentice A, Singla A (2007). Farquhar C (ed.). "Danazol for pelvic pain associated with endometriosis". Cochrane Database of Systematic Reviews (4): CD000068. doi:10.1002/14651858.CD000068.pub2. PMID 17943735.
  11. ^ a b c d e "Danazol Monograph for Professionals". Drugs.com. Archived from the original on 12 May 2021. Retrieved 28 December 2021.
  12. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 345–. ISBN 978-1-4757-2085-3.
  13. ^ Howard W. Jones; John A. Rock (10 July 2015). Te Linde's Operative Gynecology. Wolters Kluwer Health. pp. 1327–1330. ISBN 978-1-4963-1521-2. Archived from the original on 10 January 2020. Retrieved 26 December 2020.
  14. ^ a b "Danazol Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 6 May 2016. Retrieved 28 December 2021.
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