Isolation, synthesis, and biological activity of five metabolites of danazol
| Autor: | Robert G. Christiansen, Gordon O. Potts, H. P. Schane, H. C. Neumann, D. Rosi |
|---|---|
| Rok vydání: | 1977 |
| Předmět: |
Male
Urine Pharmacology Genitalia Male chemistry.chemical_compound Estrus Fusarium Pregnancy Pregnadienes Drug Discovery medicine Endocrine system Animals Humans Hydroxymethyl Gonadotropins pituitary Arthrobacter Danazol Pituitary gonadotropin Ovary Biological activity Haplorhini Organ Size Macaca mulatta Rats chemistry Fermentation Gonadotropins Pituitary Molecular Medicine Female Rhizopus Hormone medicine.drug |
| Zdroj: | Journal of medicinal chemistry. 20(3) |
| ISSN: | 0022-2623 |
| Popis: | 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.Urinary metabolites of danazol (17alpha-pregna-2,4-dien-20-yno (2,3-delta)isoxazol-17-01), and inhibitor of pituitary gonadotropins, were isolated from a woman who had been taking the drug orally at a dose of 800 mg/day for 7 days. The isolated metabolites were 17-hydroxy-17alpha-pregn-4-en-20-yn-3-one, 17-hydroxy-2alpha-(hydroxymethyl)-17alpha-pregn-4-en-20-yn-3-one, 47-hydroxy-2-(hydroxymethyl)-17alpha-pregna-1,4-dien-20-yn-3-one, 6beta,17-dihydroxy-2alpha-(hydroxymethyl)-17alpha-pregn-4-en-20-yn-3-one and 6beta,17-dihydroxy-2-(hydroxymethyl)-17alpha-pregna-1,4-dien-20-yn-3-one. The pituitary inhibiting activity of these metabolites was less than that of danazol. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|