Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overview
- PMID: 34004039
- DOI: 10.1002/elps.202100032
Chiral separation in the class of proton pump inhibitors by chromatographic and electromigration techniques: An overview
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.
© 2021 Wiley-VCH GmbH.
Similar articles
-
Stereoselective disposition of proton pump inhibitors.Clin Drug Investig. 2008;28(5):263-79. doi: 10.2165/00044011-200828050-00001. Clin Drug Investig. 2008. PMID: 18407713 Review.
-
Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities.Drug Metab Dispos. 2004 Aug;32(8):821-7. doi: 10.1124/dmd.32.8.821. Drug Metab Dispos. 2004. PMID: 15258107
-
Evaluation of six proton pump inhibitors as inhibitors of various human cytochromes P450: focus on cytochrome P450 2C19.Drug Metab Dispos. 2012 Sep;40(9):1698-711. doi: 10.1124/dmd.112.045575. Epub 2012 May 30. Drug Metab Dispos. 2012. PMID: 22648560
-
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality.Scand J Gastroenterol Suppl. 2001;(234):3-9. doi: 10.1080/003655201753265389. Scand J Gastroenterol Suppl. 2001. PMID: 11768559
-
[New-generation proton pump inhibitors: progress in the treatment of peptic acid diseases?].Presse Med. 2004 Jun 19;33(11):746-54. doi: 10.1016/s0755-4982(04)98731-3. Presse Med. 2004. PMID: 15257232 Review. French.
Cited by
-
Proton pump inhibitors display anti-tumour potential in glioma.Cell Prolif. 2023 Jul;56(7):e13321. doi: 10.1111/cpr.13321. Epub 2022 Aug 12. Cell Prolif. 2023. PMID: 35961680 Free PMC article. Review.
-
Enantioseparation of Proton Pump Inhibitors by HPLC on Polysaccharide-Type Stationary Phases: Enantiomer Elution Order Reversal, Thermodynamic Characterization, and Hysteretic Effect.Int J Mol Sci. 2025 Jul 25;26(15):7217. doi: 10.3390/ijms26157217. Int J Mol Sci. 2025. PMID: 40806345 Free PMC article.
-
Formulation of Dosage Forms with Proton Pump Inhibitors: State of the Art, Challenges and Future Perspectives.Pharmaceutics. 2022 Sep 25;14(10):2043. doi: 10.3390/pharmaceutics14102043. Pharmaceutics. 2022. PMID: 36297478 Free PMC article. Review.
References
7 References
-
- Wermuth, C. G., in: Wermuth, C., Aldous, D., Raboisson, P., Rognan, D. (Eds.), The Practice of Medicinal Chemistry, 4th ed., Elsevier, Amsterdam 2015, pp. 429-447.
-
- Agranat, I., Caner, H., Caldwell, J., Nat. Rev. Drug Discovery 2002, 1, 753-768.
-
- Agranat, I., Wainschtein, S. R., Zusman, E. Z., Nat. Rev. Drug Discovery 2012, 11, 972-973.
-
- Calcaterra, A., D'Acquarica, I., J. Pharm. Biomed. Anal. 2018, 147, 323-340.
-
- U. S. Food and Drug Administration (FDA), CDER New Drugs at FDA: CDER's New Molecular Entities and New Therapeutic Biological Products, https://www.fda.gov/drugs/development-approval-process-drugs/newdrugs-fd... [accessed Jan 20, 2021].
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous