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.

Abstract

Six proton pump inhibitors (PPIs), omeprazole, lansoprazole, esomeprazole, dexlansoprazole, pantoprazole, and rabeprazole, were shown to be weak inhibitors of cytochromes P450 (CYP3A4, -2B6, -2D6, -2C9, -2C8, and -1A2) in human liver microsomes. In most cases, IC₅₀ values were greater than 40 μM, except for dexlansoprazole and lansoprazole with CYP1A2 (IC₅₀ = ∼8 μM) and esomeprazole with CYP2C8 (IC₅₀ = 31 μM). With the exception of CYP2C19 inhibition by omeprazole and esomeprazole (IC₅₀ ratio, 2.5 to 5.9), there was no evidence for a marked time-dependent shift in IC₅₀ (IC₅₀ ratio, ≤ 2) after a 30-min preincubation with NADPH. In the absence of preincubation, lansoprazole (IC₅₀ = 0.73 μM) and esomeprazole (IC₅₀ = 3.7 μM) were the most potent CYP2C19 inhibitors, followed by dexlansoprazole and omeprazole (IC₅₀ = ∼7.0 μM). Rabeprazole and pantoprazole (IC₅₀ = ≥ 25 μM) were the weakest. A similar ranking was obtained with recombinant CYP2C19. Despite the IC₅₀ ranking, after consideration of plasma levels (static and dynamic), protein binding, and metabolism-dependent inhibition, it is concluded that omeprazole and esomeprazole are the most potent CYP2C19 inhibitors. This was confirmed after the incubation of the individual PPIs with human primary hepatocytes (in the presence of human serum) and by monitoring their impact on diazepam N-demethylase activity at a low concentration of diazepam (2 μM). Data described herein are consistent with reports that PPIs are mostly weak inhibitors of cytochromes P450 in vivo. However, two members of the PPI class (esomeprazole and omeprazole) are more likely to serve as clinically relevant inhibitors of CYP2C19.

Publication types

  • Comparative Study

MeSH terms

  • 2-Pyridinylmethylsulfinylbenzimidazoles / pharmacology
  • Aryl Hydrocarbon Hydroxylases / antagonists & inhibitors*
  • Aryl Hydrocarbon Hydroxylases / metabolism
  • Biotransformation
  • Cells, Cultured
  • Computer Simulation
  • Cytochrome P-450 CYP2C19
  • Dealkylation
  • Dexlansoprazole
  • Diazepam / metabolism
  • Dose-Response Relationship, Drug
  • Drug Interactions
  • Enzyme Inhibitors / pharmacology*
  • Esomeprazole / pharmacokinetics
  • Esomeprazole / pharmacology*
  • Hepatocytes / drug effects
  • Hepatocytes / enzymology
  • Humans
  • Kinetics
  • Lansoprazole
  • Liver / drug effects*
  • Liver / enzymology
  • Microsomes, Liver / enzymology
  • Models, Biological
  • NADP / metabolism
  • Omeprazole / pharmacokinetics
  • Omeprazole / pharmacology*
  • Pantoprazole
  • Proton Pump Inhibitors / pharmacokinetics
  • Proton Pump Inhibitors / pharmacology*
  • Rabeprazole
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Substrate Specificity

Substances

  • 2-Pyridinylmethylsulfinylbenzimidazoles
  • Enzyme Inhibitors
  • Proton Pump Inhibitors
  • Recombinant Proteins
  • Lansoprazole
  • Rabeprazole
  • NADP
  • Pantoprazole
  • Aryl Hydrocarbon Hydroxylases
  • CYP2C19 protein, human
  • Cytochrome P-450 CYP2C19
  • Omeprazole
  • Esomeprazole
  • Diazepam
  • Dexlansoprazole