Isolation, synthesis, and biological activity of five metabolites of danazol
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Five danazol metabolites were isolated from urine and synthesized, but none showed significant pituitary inhibiting activity compared to danazol.
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Abstract
Metabolites of danazol (17 alpha-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol), an orally effective pituitary gonadotropin inhibitory agent devoid of estrogenic and progestational activites, were isolated from urine of a female subject who had taken danzol orally at a dose of 800 mg/day for 7 days, The metabolites isolated were 17-hydroxy-17alpha-pregn-4-en-20-yn-3-one (11), 17-hydroxy-2alpha-(hydroxymethyl)-17alpha-pregn-4-3n-20-yn-3-one (5), 17-hydroxy-2-(hydroxymethyl)-17alpha-pregna-1,4-dien-20-yn-3-one(7), 6beta,17-dihydroxy-2alpha-(hydroxymethyl)-17alphapregn-4-en-20-yn-3-one(8), and 6beta, 17-dihydroxy-2(hydroxymethyl)-17alphapregna-1,4-dien-20yn-3-one(10). None of these metabolites exhibited pituitary inhibiting activity comparable to danazol.
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Cited by (12)
- Danazol 2022
- A Benefit-Risk Assessment of Medical Treatment for Uterine Leiomyomas 2002
- Prolonged inhibition of normal ovarian cycles in the rat and cynomolgus monkeys following a single s.c. injection of danazol 1997
- A liquid chromatographic method for the determination of danazol in human serum 1990
- Analysis of danazol in serum using high-performance liquid chromatography 1987
- Determination of danazol in pharmaceutical preparations by liquid chromatography 1986
- The effect of danazol on gonadotropin secretion during the follicular phase of the menstrual cycle 1983
- Hormonal and Surgical Management of Pelvic Endometriosis 1982
- Danazol Binding to Rat Androgen, Glucocorticoid, Progesterone, and Estrogen Receptors: Correlation With Biologic Activity 1979
- A radioimmumoassay for danazol (17α-Pregna-2,4-Dien-20-Yno[2,3-d]Isoxazol-17-OL) 1978
- Radioimmunoassay for Danazol in Human and Monkey Plasma 1978
- ChemInform Abstract: ISOLATION, SYNTHESIS, AND BIOLOGICAL ACTIVITY OF FIVE METABOLITES OF DANAZOL 1977
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