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 antihysterotrophic1–4. 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 that5,6. 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.
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MARDONES, E., IGLESIAS, R. & LIPSCHUTZ, A. Antiœstrogenic Potencies of Various Progesterone Derivatives with Oxidation at C11 . Nature 174, 839–840 (1954). https://doi.org/10.1038/174839a0