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SOME CHEMICAL AND BIOLOGICAL PROPERTIES OF 19-NOR-17?-ETHYNYLTESTOSTERONE

1958; Wiley; Volume: 71; Issue: 5 New Steriod C Linguagem: Inglês

10.1111/j.1749-6632.1958.tb46781.x

1749-6632

Daniel A. McGinty, Carl Djerassi,

Estrogen and related hormone effects

A brief chronological discussion of the chemistry of 19-nor steroids was presented and details concerning the syntheses of the progestationally active 19-nor-17alpha-ethinyltestosterone (Norlutin) and 19-nor-17alpha-methyltestosterone were given. The oral progestational activity of Norlutin and of the methyl ethyl and vinyl analogs in rabbits is approximately 5 times that of 17alpha-ethinyltestosterone. Norlutin is equally potent intramuscularly but is not active on direct application to the rabbit uterus. The reason for this lack of progestational activity by intrauterine administration is not known but it may be due to interference by contaminating estrogen. The oral estrogenic activity of Norlutin is relatively low. Norlutin is negligibly androgenic differing in this respect from the other 17-substituted derivatives studied. Norlutin is antigonadotropic. This property is shared by the 19-nor-17alpha-methyl ethyl and vinyl analogs and also by 17alpha-methyltestosterone but is obscured to varying degrees by the direct androgenic action of these compounds on the target organs. The possibility that suppression of pituitary secretion of gonadotropin by Norlutin may be due to contaminating 17alpha-ethinylestradiol 3-methyl ether or to the formation of 17alpha-ethinylestradiol from Norlutin in the intestinal tract is discussed. Norlutin and (to a lesser degree) 19-nor-17alpha-methyltestosterone exhibit an anabolic or anticatabolic action by counteracting loss in liver weight (and nitrogen) due to fasting. This effect while shown by 17alpha-ethinylestradiol 3-methyl ether is not due entirely to contamination of Norlutin by this estrogen. 17alpha-methyltestosterone is inactive in this test. Norlutin also accelerates slightly the restoration of liver mass following partial hepatectomy.