title: Anti-androgen TSAA-291. VII. On the mechanism of anti-androgenic action of 16 beta-ethyl-17 beta-hydroxy-4-oestren-3-one (TSAA-291).
abstract: The mechanism of anti-androgenic action of a steroidal compound, TSAA-291, was summarized and discussed in reference to its drug-designing and structure-activity relationship. The target of the drug-design was to obtain a substance which is inactive in androgenic activity and is capable of antagonistically competing with androgen for the receptor. With this intention, the androgen molecule was rendered with a steric hindrance influencing upon the functional 17 beta-hydroxy group. Introduction of a bulky group at the steroidal position-13 or -16 led to anti-androgenic properties. Intense steric hindrance by introducing an enormously bulky group or complete elimination of the 17 beta-hydroxy group rather decreased the anti-androgenic activity. Of these anti-androgens thus synthesized, TSAA-291 proved to be the most active in the anti-androgen assay and also antagonistic against the uptake of [3H]testosterone by the rat ventral prostate.
mesh_terms: D000726:Androgen Antagonists / Q000008:administration & dosage / Q000494:pharmacology; D000818:Animals; D002369:Castration; D055598:Chemical Phenomena; D002621:Chemistry; D007279:Injections, Subcutaneous; D008297:Male; D009277:Nandrolone / Q000031:analogs & derivatives* / Q000494:pharmacology; D009929:Organ Size / Q000187:drug effects; D011467:Prostate / Q000187:drug effects; D051381:Rats; D012669:Seminal Vesicles / Q000187:drug effects; D013739:Testosterone / Q000378:metabolism / Q000494:pharmacology
chemical_list: D000726:Androgen Antagonists; D013739:Testosterone; D009277:Nandrolone