Biological Activities of 16 , 17 Dihydroxyprogesterone Derivatives

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Abstract
A series of compounds derived from 16[alpha], 17[alpha]-dihydroxyprogesterone (DHP) was assayed for parenteral and oral progestational activity by the McPhail rabbit method. The 16[alpha], 17[alpha]-acetophenone (P-DHP) and 16[alpha], 17[alpha]-acetone (A-DHP) derivatives were equipotent parenterally and approximately twice as potent as progesterone. P-DHP was 1-2 times as potent orally as norethisterone but A-DHP was only weakly active by the oral route. Parenteral activity was not significantly altered by 6[alpha]- or 6[beta]-methylation of P-DHP or A-DHP. Oral potency of P-DHP was not altered by 6[beta]-methylation but was reduced by 6[alpha]-methylation. The 6-methyl derivatives of A-DHP were more active orally than A-DHP. 6[alpha]-Fluoro P-DHP and 6[alpha]-fluoro-A-DHP were equal to or slightly more active parenterally and less active orally than the parent steroids. 6[beta]-fluorination abolished progestational activity of both compounds by either route of administration. Duration of the progestational effect of P-DHP and A-DHP following a single intramuscular injection was of 25 and 20 days respectively. P-DHP was not androgenic, anti-androgenic, estrogenic, anti-DCA or glucocorticoid-like in its activities.