50679-08-8 特非那定

特非那定

英文名称:1-(4-tert-butylphenyl)-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butan-1-ol
CAS:

50679-08-8

分子式:C32H41NO2
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特非那定简介

Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. It was brought to market by Hoechst Marion Roussel (now Sanofi-Aventis) and was marketed under various brand names, including Seldane in the United States, Triludan in the United Kingdom, and Teldane in Australia. It was superseded by fexofenadine in the 1990s due to the risk of a particular type of disruption of the electrical rhythms of the heart (specifically cardiac arrhythmia caused by QT interval prolongation) and has been withdrawn from markets worldwide.:53; Terfenadine is a prodrug, generally completely metabolized to the active form fexofenadine in the liver by the enzyme cytochrome P450 3A4. Due to its near complete metabolism by the liver immediately after leaving the gut, terfenadine normally is not measurable in the plasma. Terfenadine itself, however, is cardiotoxic at higher doses, while its major active metabolite is not. Terfenadine, in addition to its antihistamine effects, also acts as a potassium channel blocker (Kv11.1 encoded by the gene hERG). Since its active metabolite is not a potassium channel blocker, no cardiotoxicity is associated with fexofenadine. Toxicity is possible after years of continued use with no previous problems as a result of an interaction with other medications such as erythromycin, or foods such as grapefruit. The addition of, or a dosage increase in, these CYP3A4 inhibitors makes it harder for the body to metabolize and remove terfenadine. In larger plasma concentrations, it may lead to toxic effects on the heart's rhythm (e.g. ventricular tachycardia and torsades de pointes).

特非那定基本信息

中文名称 特非那定 英文名称 1-(4-tert-butylphenyl)-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butan-1-ol
中文别名

α-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; alpha-[4-叔丁基苯基]-4-(羟基二苯基甲基)-1-哌啶丁醇; Α-[4-叔丁基苯基]-4-(羟基二苯基甲基)-1-哌啶丁醇; Α-[4-(1,1-二甲基乙基)苯基]-4-(羟基二苯甲基)-1-哌啶丁醇; 叔哌丁醇;

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英文别名

Triludan; Teldane; Teldanex; [3H]-Terfenadine; Allerplus; Seldane; Terdin; Terfenadina; Aldaban; Terfenadine; [14C]-Terfenadine; Ternadin;

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CAS号 50679-08-8 分子式 C32H41NO2
分子量 471.67300 精确质量 471.31400
PSA 43.70000 LOGP 6.38370

特非那定编号系统

UNII 7BA5G9Y06Q

特非那定物化性质

外观与性状:
固体结晶粉末
密度:
1.088 g/cm3
沸点:
626.8ºC at 760 mmHg
熔点:
145-152 °C
闪点:
306.9ºC
水溶解性:
0.001 g/100 mL (30 ºC)
储存条件:
2-8ºC

安全信息

RTECS号:
TM4969000
安全说明:
S24/25
WGK Germany:
2
海关编码:
2933399090
危险性描述:
H413

生产方法及用途

生产方法

α,α-二苯基-4-哌啶基甲醇(107g,0.4m
o1)(其制备参见McCarty F J,et a1.J Org Chem,1961,26:40
84)、1-[4-(1,1-二甲基乙基)苯基]-4-氯-1-丁酮(105g,0.44m
o1)(其制备参见Van de Westerign C,et a1.Ind chim beige,1960,25:1073;CA 55:6428b.19
61)、碳酸氢钾(70g,0.7m
o1)和0.1g碘化钾在600ml甲苯中,搅拌回流60h。反应液乘热过滤,滤液冷却后和过量的氯化氢乙醚溶液作用。过滤收集产生的沉淀,用甲醇-异丙醇(5:
12)重结晶,得78.4g化合物(I),收率24%。化合物(I)(60g,0.12m
o1)溶于1.
2 L甲醇,加入氢氧化钾的甲醇溶液至反应液呈碱性。然后冷至01;,在搅拌下分批加入硼氢化钾(5g,0.132m
o1)。移去冷却,搅拌1h。在蒸汽浴上减压浓缩,得到固体剩余物。该固体用水洗后,以丙酮重结晶2次,得34.4g特非那定,收率61.5%。

用途

新型抗组胺药,有特异的外周H1受体拮抗作用,且没有抗5-羟色胺、抗胆碱能和抗肾上腺素能的作用。适用于季节性过敏性鼻炎(花粉症)、常年性过敏鼻炎、急慢性荨麻疹等的治疗。

SDS 1.0 中文 展开
SDS 1.0 英文 展开
1H NMR : Predict展开

核磁图谱 1H NMR : Predict

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国家名称 海关编码 海关数据更新时间 操作
中国 2933399090 2019-03 申报要素
美国 2933399100 2019-03 概述
印度 29333920 2019-03 概述
欧盟 29333999 2019-03 概述
英国 2933399990 2019-03 概述
日本 293339220 2019-03 概述
韩国 2933399000 2019-03 概述
加拿大 2933390020 2019-03 概述
特非那定
CAS号:50679-08-8 分子式:C32H41NO2 分子量:471.67300

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