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Danazol
Chemical compound / From Wikipedia, the free encyclopedia
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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.[6][2][10][11][12] It is taken by mouth.[2]
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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 |
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Routes of administration | By mouth |
Drug class | Androgen; Anabolic steroid; Progestogen; Progestin; Antigonadotropin; Steroidogenesis inhibitor; Antiestrogen |
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Bioavailability | Saturable with dosage, higher with food intake[2] |
Protein binding | To albumin, SHBGTooltip sex hormone-binding globulin, CBGTooltip corticosteroid-binding globulin[3][4][5] |
Metabolism | Liver (CYP3A4)[6][7] |
Metabolites | • 2-OHM-Ethisterone[7] • Ethisterone[8][9] |
Elimination half-life | Acute: 3–10 hours[6][2] Chronic: 24–26 hours[6] |
Excretion | Urine, feces[6][2] |
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ECHA InfoCard | 100.037.503 ![]() |
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Formula | C22H27NO2 |
Molar mass | 337.463 g·mol−1 |
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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Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by gonadotropin-releasing hormone analogues (GnRH analogues) in the treatment of endometriosis.[4]