化合物简介
Nefazodone (Dutonin, Nefadar, Serzone) is an antidepressant marketed by Bristol-Myers Squibb. Its sale was discontinued in 2003 in some countries due to the rare incidence of hepatotoxicity (liver damage), which could lead to the need for a liver transplant, or even death. The incidence of severe liver damage is approximately 1 in every 250,000 to 300,000 patient-years. On June 14, 2004, Bristol-Myers Squibb discontinued the sale of Serzone in the United States and Canada. Several generic formulations of nefazodone are still available.
基本信息
中文名称
耐法唑酮
英文名称
nefazodone
中文别名
2-[3-[4-(3-氯苯基)-1-哌嗪基]丙基]-5-乙基-2,4-二氢-4-(2-苯氧基乙基)-3H-1,2,4-三唑-3-酮、奈法唑酮
英文别名
2-<3-<4-(3-chlorophenyl)-1-piperazinyl>propyl>-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazolin-3-one、Nefazodonum [Latin]、Nefazodonum、2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-5-ethyl-4-(2-phenoxyethyl)-1,2,4-triazol-3-one、2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one、Nefazodone (INN)、UNII-59H4FCV1TF、Nefazodona [Spanish]、Nefazodone Hcl、2-[3-[4-(3-chlorophenyl)-1-piperazinyl]-propyl-]5-ethyl-2,4-dihydro-4-(2-phenoxy-ethyl)-3H-1,2,4-triazol-3-one、[14C]-Nefazodone hydrochloride、Nefazodona
CAS号
83366-66-9
分子式
C25H32ClN5O2
分子量
470.007
精确质量
469.224
PSA
55.53
LOGP
3.5548
编号系统
UNII
59H4FCV1TF
物化性质
外观与性状
白色至灰白色结晶粉末
熔点
180-182°C
安全信息
安全说明
S22-S24/25
WGK Germany
3
生产方法及用途
生产方法
化合物(I)和1-溴-3-氯丙烷反应，N-烷化得到化合物(Ⅱ)，收率66%。(Ⅱ)用肼处理，得到92%收率的化合物(Ⅲ)。(Ⅲ)和(硫代丙酰氨基)甲酸乙酯在乙醇中反应，生成三唑(Ⅳ)，收率72%。(Ⅳ)在氢氧化钠作用下，用苯氧基乙基溴进行N-烷化反应，得到奈法唑酮，收率53%。
用途
抗抑郁剂。为苯基哌嗪类衍生物，对5-HT具有双重作用。
合成路线
上游原料
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