A new class of long-acting hormonal steroid preparation: synthesis of dimeric androgenes coupled at C3-C3 and C17-C3 and of an androgen-progestogen combination.
3beta-Hydroxy-4-androsten-17-one was prepared from 4-androsten-3,17-dione according to the method of Klimstra and Colton (1) and dimerized by means of esterification with succinic acid. The reduction with lithium-tri-t-butoxyaluminium hydride gave a testosterone derivative coupled between C3-C3 which showed after a single injection of 10 mg a protracted but relatively weak androgenic effect in castrated male rats. The direct esterification of testosterone hemisuccinate with 4-androsten-3beta, 17beta-diol gave the testosterone derivative coupled between C17-C3 which showed a more even and more protracted time response curve than testosterone enanthate. The testosterone-ethynodiol succinate also coupled between C17-C3, showed an androgenic depot-effect similar to that of the dimeric C17-C3 testosterone derivative.
D000818:Animals; D002369:Castration; D005040:Ethynodiol Diacetate; D006537:Heptanoates; D008297:Male; D051381:Rats; D012669:Seminal Vesicles / Q000187:drug effects; D013739:Testosterone; D045165:Testosterone Congeners / Q000138:chemical synthesis* / Q000494:pharmacology
D006537:Heptanoates; D045165:Testosterone Congeners; D013739:Testosterone; D005040:Ethynodiol Diacetate