Nature 174, 839 - 840 (30 October 1954); doi:10.1038/174839a0

Antistrogenic Potencies of Various Progesterone Derivatives with Oxidation at C₁₁

ELVIRA MARDONES, RIGOBERTO IGLESIAS & A. LIPSCHUTZ

Institute of Experimental Medicine, National Health Service of Chile, Av. Irarrázaval 849, Santiago. June 19.

EVIDENCE has been given that certain antistrogenic 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--hydroxyprogesterone and 11--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.

1. Lipschutz, A. , Iglesias, R. , and Mardones, E. , Bull. Assoc. Franç. Cancer, 38, 394 (1950).
2. Lipschutz, A. , Mardones, E. , Iglesias, R. , Fuenzalida, F. , and Bruzzone, S. , Science, 116, 448 (1952). | PubMed | ISI | ChemPort |
3. Mardones, E. , Iglesias, R. , Fuenzalida, F. , Bruzzone, S. , and Lipschutz, A. , Nature, 170, 917 (1952); 171, 1026 (1953). | PubMed | ChemPort |
4. Mardones, E. , Bruzzone, S. , Inglesias, R. , and Lipschutz, A. , Endocrin., 49, 817 (1951). | ISI | ChemPort |
5. Byrnes, W. W. , Stafford, R. D. , and Olson, K. J. , Proc. Soc. Exp. Biol. and Med., 82, 243 (1953). | ISI | ChemPort |
6. Byrnes, W. W. (private communication).