Metabolites of dihydrotachysterol in target tissues.
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Eight androstane derivatives with modified ring A or B (4,5-secoandrostanes and ring B cyclopropanoandrostanes) were assayed in vivo on mice for their antiandrogenic activity and the effect was compared with that of cyproterone acetate. The inhibition of dihydrotestosterone binding to rat prostate cytosol and to human plasmatic sex hormone binding protein was correlated with the in vivo effect. The antiandrogenic activity of 6 alpha,7 alpha-cyclopropano-5 alpha-androstane-3 beta,17 beta-diol was nearly as high as that of cyproterone acetate. The opening of ring A of androgens, such as testosterone or 17 alpha-methyltestosterone, moderately reduced the binding and changed the biological activity to weakly antiandrogenic.
Doisynolic acids are alkaline degradation products of steroidal estrogens. While these doisynolic acids are potent estrogens, some being more estrogenic than estradiol itself, they bind to cytoplasmic estrogen receptors only feebly compared with estradiol.
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The reaction with maleic anhydride yielding Diels-Alder adducts is used to distinguish vitamin D isomers. Treatment at 100 degrees C for 3 hr eliminates the fast-reacting (tachysterol and trans-vitamin D) and slow-reacting (cis-vitamin D and previtamin D) isomers. However, isotachysterol is not eliminated. The procedure has been incorporated as a confirmation test for isotachysterol in the official final action method for the determination of vitamin D in concentrates, 43.B14-43.B24.
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