Oxendolone (INN, USAN, JAN) (brand name Prostetin; former developmental code name TSAA-291), also known as 16β-ethyl-19-nortestosterone or 16β-ethyl-17β-hydroxy-4-estren-3-one, is a steroidal antiandrogen and progestin of the 19-nortestosterone group that has been marketed in Japan by Takeda for the treatment of benign prostatic hyperplasia (BPH) since 1981. It binds to the androgen receptor (AR) (Ki = 320 nM) and progesterone receptor (Ki = 20 nM) and acts as a weak but clinically relevant inhibitor of 5α-reductase (IC50 = 1.4 μM). The binding affinity of oxendolone for the AR is far lower than that of cyproterone acetate. At the AR, oxendolone is not a silent antagonist but is rather predominantly antagonistic with weak agonistic activity; for this reason, it has been described as a selective androgen receptor modulator. The drug has antigonadotropic properties via its progestogenic actions. Although oxendolone is approved for the treatment of BPH in Japan, concerns have been raised about its use for this condition due to poor efficacy seen in clinical trials.

CAS：33765-68-3
中文别名：
英文别名：Oxendolona [INN-Spanish];Oxendolone [USAN:INN:JAN];Tsaa 291;oxendolone;Oxendolona;Prostetin;Oxendolonum [INN-Latin];
分子式：C20H30O2
分子量：302.451
精确质量：302.225
Psa：37.3
Logp：4.1252

UNII：MN4I850D4P

密度：1.1g/cm3
沸点：451.7ºC at 760mmHg
闪点：192.4ºC
折射率：1.553

生产方法
将雌酚酮、二氯甲烷、氢氧化钠、三乙基苄铵盐和水,室温搅拌下,滴加硫酸二甲酯,进行甲基化反应。该甲基化产物、对甲苯磺酸和异丙烯基乙酸酯,搅拌回流,得烯醇化产物。该产物、氧化镁和二氯甲烷构成的溶液中,滴加单过氧邻苯二甲酸的乙醚溶液,进行环氧化反应。在室温和搅拌下,往环氧化产物的冰乙酸溶液中,滴加冰乙醇和硫酸的混合液,反应使环氧开环。开环产物和氢氧化钾的甲醇溶液,搅拌回流。再在四氢呋喃中,加乙基溴化镁格氏试剂,进行格氏反应。该反应产物、对甲苯磺酸和冰乙酸,搅拌回流,然后用硼氢化钠在甲醇中进行还原。最后在四氢呋喃溶液中,通入液氨,在搅拌下再缓慢加入锂,还原得奥生多龙。或者将16β-乙基雄甾-4-烯-3,17-二酮溶于二氧六环,加入原甲酸乙酯和对甲苯磺酸,在室温下搅拌,得到3-乙氧基-16β-乙基雄甾-3,5-二烯-17-酮。将其溶于甲醇,加入硼氢化钠,在室温下搅拌,还原得3-乙氧基-16-β-乙基雄甾-3,5-二烯-17β-醇。最后溶于甲醇,加入浓盐酸,水解即得奥生多龙。 抗雄性激素药物,有抗雄性激素作用。在前列腺直接与雄性激素发生竞争性拮抗,抑制前列腺及精囊的重量。其抗雄激素作用特异性高,在前列腺直接与雄激素发生竞争性拮抗而几乎不显示其他激素作用。适用于治疗前列腺肥大。用于前列腺肥大的治疗。
用途
抗雄性激素药物,有抗雄性激素作用。在前列腺直接与雄性激素发生竞争性拮抗,抑制前列腺及精囊的重量。其抗雄激素作用特异性高,在前列腺直接与雄激素发生竞争性拮抗而几乎不显示其他激素作用。适用于治疗前列腺肥大。用于前列腺肥大的治疗。