Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overview

Electrophoresis. 2021 Sep;42(17-18):1761-1789. doi: 10.1002/elps.202100032. Epub 2021 May 27.

Abstract

Proton pump inhibitors (PPIs) are benzimidazole-derivative chiral sulfoxides, frequently used in the treatment of gastric hyperacidity-related disorders. Due to their stereoselective metabolism, the eutomeric forms of PPIs can present a more advantageous pharmacokinetic profile by comparison with the distomers or racemates. Moreover, two representatives of the class are used in therapy both as racemates and as pure enantiomers (esomeprazole, dexlansoprazole). A relatively large number of enantioseparation methods employed for the stereoselective determination of PPIs from pharmaceutical, biological, and environmental matrices were published in the past three decades. The purpose of the current overview is to provide a systematic survey of the available chiral separation methods published since the introduction of PPIs in the therapy up to the present. Analytical and bioanalytical methods using different chromatographic and electromigration techniques reported for the enantioseparation of omeprazole, lansoprazole, pantoprazole, rabeprazole, ilaprazole, and tenatoprazole are included. The analytical conditions of the presented methods are summarized in three comprehensive tables, while a critical discussion of the applied techniques, possible mechanism of enantiorecognition, and future perspectives on the topic are also presented.

Keywords: Chiral separation; Chromatography; Electrophoresis; Pharmaceutical analysis; Proton pump inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • 2-Pyridinylmethylsulfinylbenzimidazoles
  • Electrophoresis*
  • Esomeprazole
  • Omeprazole
  • Pantoprazole
  • Proton Pump Inhibitors
  • Rabeprazole

Substances

  • 2-Pyridinylmethylsulfinylbenzimidazoles
  • Proton Pump Inhibitors
  • Rabeprazole
  • Pantoprazole
  • Omeprazole
  • Esomeprazole