First total synthesis of 3a-hydroxy-1,1-dimethyl-5-((N-methylsulfamoyl) methyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-1-ium 2,2,2-trifluoroacetate by mimicking the oxidative degradation pathway of sumatriptan

被引：3

作者：

Sasmal, Pradip K. ^{[1
]}

Ramachandran, Ganesh ^{[1
]}

Zhang, Ying ^{[2
]}

Liu, Zhong ^{[2
]}

机构：

[1] Dr Reddys Labs Ltd, Proprietary Prod, Hyderabad 500090, India

[2] Pharmaron Xian Co Ltd, 1 12th Fengcheng Rd, Xian 710018, Shanxi, Peoples R China

来源：

RESULTS IN CHEMISTRY | 2021年 / 3卷

关键词：

Sumatriptan; Zembrace; Degradation; Oxidative cyclization; MIGRAINE ATTACKS;

D O I：

10.1016/j.rechem.2021.100173

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The expiry date of any medicine is decided based on the time span during which the drug product maintains its quality and is safe as well as effective. The levels of various impurities present in any drug product are considered safe based on various toxicological studies in preclinical species and safety parameters monitoring during clinical studies. The shelf life of US FDA approved sumatriptan auto-injector product ZEMBRACE SymTouch was extended till 36 months after toxicological qualification of the degradation compound 3a-hydroxy-1,1-dimethyl-5-((N-methylsulfamoyl)methyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-1-ium 2,2,2-trifluoroacetate. The first total synthesis of this degradation product by mimicking the oxidative degradation pathway of sumatriptan is described herein. (c) 2021 Elsevier Science. All rights reserved.

引用

页数：4