Antiœstrogenic Potencies of Various Progesterone Derivatives with Oxidation at C₁₁

Abstract

EVIDENCE has been given that certain antiœstrogenic potencies of progesterone such as the antifibromatogenic, antihysterotrophic and antiluteinizing ones are diminished by oxidation at C₂₁, Cu₁₁ and C₁₇. Thus, deoxycorticosterone (C₂₁—OH) is less anti-fibromatogenic and less antiluteinizing than progesterone; dehydrocorticosterone, or substance A of Kendall (C₁₁=O), is less antifibromatogenie than deoxycorticosterone ; 17-hydroxy-deoxycorticosterone, or substance S of Reichstein, is neither antifibromatogenic nor antihysterotrophic^1–4. More recently, the workers of the Upjohn Co. have obtained various derivatives of progesterone by oxidation at C₁₁ such as 11-keto-progesterone, 11-α-hydroxyprogesterone and 11-β-hydroxyprogesterone; these compounds, when tested in various ways, have been found to be only about 3–10 per cent as progestational as progesterone, or even less than that^5,6. Our former knowledge of the diminution of the antifibromatogenic potency through oxidation at C₁₁ has been obtained only in comparative work with deoxycorticosterone and dehydrocorticosterone³; this is why we thought it convenient to test the three new C₁₁-derivatives of progesterone mentioned as to their antifibromatogenic and antihysterotrophic potencies.