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化合物简介

Bumetanide (trade names Bumex or Burinex) is a loop diuretic of the sulfamyl category to treat heart failure. It is often used in people in whom high doses of furosemide are ineffective. It is marketed by Hoffmann-La Roche. The main difference between the two substances is in bioavailability and pharmacodynamic potency. Furosemide is incompletely absorbed in the intestine (60%), and there are substantial inter- and intraindividual differences in bioavailability (range 10-90%). Bumetanide is almost completely absorbed (80%), and the absorption is not altered when it is taken with food. It is said to be a more predictable diuretic, meaning that the predictable absorption is reflected in a more predictable effect.

基本信息

CAS:28395-03-1
中文别名:强力速效利尿剂;5-正丁氨基-4-苯氧基-3-氨基磺酰基苯甲酸;3-(氨基磺酰基)-5-(丁基氨基)-4-苯氧基苯甲酸;3-正丁胺基-4苯氧基-5-氨基磺酰苯甲酸;
英文别名:Bumetanide;Fordiuran;3-(Aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid;3-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid;3-(aminosulfonyl)-5-(butylamino)-4-phenoxybenzoic acid;Bumetanida;Bumex;Bumetanidum;2-phenoxy-3-butylamino-5-carboxybenzenesulfonamide;3-(butylamino-)-4-phenoxy-5-sulfamoylbenzoic acid;[3H]-Bumetanide;Fontego;Burinex;3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid;Lunetoron;Segurex;
分子式:C17H20N2O5S
分子量:364.416
精确质量:364.109
Psa:127.1
Logp:4.8906

编号系统

MDL号:MFCD00078949

物化性质

外观与性状:结晶固体
密度:1.347g/cm3
沸点:571.2ºC at 760mmHg
熔点:230-2310C
闪点:299.3ºC
折射率:1.612
稳定性:Stable at normal temperatures and pressures.
储存条件:库房通风低温干燥
蒸汽压:6.89E-14mmHg at 25°C

安全信息

RTECS号:DG4910000
WGK Germany:3
海关编码:2935009090

生产方法及用途

生产方法
1、 以对-氯苯甲酸与氯磺酸反应合成邻-氯-间-羧基苯磺酰氯。用混酸硝化生成2-氯-3-硝基-5-羧基苯磺酰氯。用氢氧化铵对磺酰氯基进行胺化得2-氯-3硝基-5-羟基-苯碘酰胺。用亚硫酸氢钠还原硝基生成乙-氯-3-氨基-5-羧基苯磺酰胺。再与丁醇反应生成乙-氯-3-丁胺基-5-甲酸丁酯苯磺酰胺。用氢氧化钠水解生成乙-氯-3-丁胺基-5-羟基-苯磺酰胺。最后与苯酚反应生成丁苯氧酸。 利尿剂,对高血压,肾功能衰竭,急性药物毒物中毒等症有预防和治疗作用。
用途
利尿剂,对高血压,肾功能衰竭,急性药物毒物中毒等症有预防和治疗作用。

合成路线

上游原料

下游产品

图谱

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