A new class of long-acting hormonal steroid preparation: synthesis of dimeric androgens coupled at C3-C3 and C-17-C3 and of an androgen-progestogen combination
| Autor: | Hans-Dieter Taubert, Herbert Kuhl |
|---|---|
| Rok vydání: | 1976 |
| Předmět: |
Male
medicine.medical_specialty medicine.drug_class medicine.medical_treatment Clinical Biochemistry Endogeny Biology Pharmacology Biochemistry Steroid Ethynodiol Diacetate chemistry.chemical_compound Endocrinology Internal medicine medicine Animals Endocrine system Testosterone Castration Testosterone Congeners Molecular Biology Progestogen Organic Chemistry Seminal Vesicles Testosterone (patch) Androgen Heptanoates Rats chemistry Succinic acid Hormone |
| Zdroj: | Steroids. 28:89-99 |
| ISSN: | 0039-128X |
| Popis: | 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.Dimeric testosterone derivatives esterified at carbon (C)17-C3 were synthesized and their androgenic depot effect was investigated. Testosterone was combined with ethynodiol in the hope of obtaining a gonadotropin-release inhibiting substance which simultaneously would substitute for the reduced endogenous androgen output. 3beta-hydroxy-4-4androsten-17-one was prepared from 4-androsten-3,17-dione 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 after a single injection of 10 mg revealed a protracted but relatively weak androgenic effect in castrated male rats. Direct esterificaiton of testosterone hemisuccinate with 4-androsten-3 beta, 17beta-diol gave the testosterone derivative coupled between C17-C3 which revealed a more even and more protracted time-response curve that testosterone enanthate. Testosterone ethynodiol succinate coupled between C17-C3 revealed an androgenic depot effect similar to that of the dimeric C17-C3 testosterone derivative. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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