Determination of enantiomeric purity of esomeprazole by capillary electrophoresis

P. Attila, Hancu Gabriel, Kelemen Hajnal, G. Árpád
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Abstract

Abstract Proton pump inhibitors are the most effective agents used in gastric hyper-acidity-related disorders. Omeprazole is a benzimidazole-derivative compound with an asymmetric sulphur in its structure, which generates its chiral character. Esomeprazole (S-omeprazole) was the first proton pump inhibitor introduced as an enantiomerically pure compound in therapy, after the successful chiral switch of the racemic omeprazole. This work is aimed at performing a complementary study to an already published chiral separation method of omeprazole. As preliminary analysis, the electrophoretic behavior of omeprazole enantiomers and the possible mechanism of the chiral resolution was studied using different background electrolytes containing different β-cyclodextrin derivatives, as chiral selectors. The robustness of the chiral separation method was tested by applying a Plackett-Burman design. The method was validated according to current ICH guidelines and proved to be reliable, linear, precise and accurate for the determination of 0.2% R-omeprazole as chiral impurity in esomeprazole samples. The validated method was successfully used for the analysis of esomeprazole-containing gastro-resistant tablets. According to our results, valuable information on the mechanism of chiral separation of omeprazole was gained and the application area of the previously developed method was successfully enlarged. The presented rapid and cost-effective capillary electrophoresis method proved to be suitable for the determination of enantiomeric purity of esomeprazole from pharmaceutical preparations and could represent an alternative for the available compendial methods.
毛细管电泳法测定埃索美拉唑对映体纯度
质子泵抑制剂是治疗胃高酸性相关疾病最有效的药物。奥美拉唑是一种苯并咪唑衍生物,其结构中含有不对称的硫,这就产生了它的手性。埃索美拉唑(s -奥美拉唑)是继外消旋奥美拉唑成功手性转换后,作为对映体纯化合物引入治疗的第一个质子泵抑制剂。这项工作的目的是对已经发表的奥美拉唑手性分离方法进行补充研究。作为初步分析,采用含有不同β-环糊精衍生物的不同背景电解质作为手性选择剂,研究了奥美拉唑对映体的电泳行为和可能的手性分辨机制。采用Plackett-Burman设计测试了手性分离方法的稳健性。根据现行ICH指南对该方法进行了验证,证明该方法可靠、线性、精确、准确,可用于测定埃索美拉唑样品中0.2% r -奥美拉唑的手性杂质。该方法可用于含埃索美拉唑抗胃片的分析。本研究为研究奥美拉唑手性分离的机理提供了有价值的信息,并成功扩大了该方法的应用领域。结果表明,该方法可用于药物制剂中埃索美拉唑对映体纯度的测定,是现有药典方法的一种替代方法。
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