Stereoselective pharmacokinetics of stable isotope (+/-)-[13C]-pantoprazole: Implications for a rapid screening phenotype test of CYP2C19 activity

Chirality. 2011 Nov;23(10):904-9. doi: 10.1002/chir.21011. Epub 2011 Sep 20.

Abstract

Aims: We have previously shown that the (±)-[(13) C]-pantoprazole breath test is a promising noninvasive probe of CYP2C19 activity. As part of that trial, plasma, breath test indices and CYP2C19 (*2, *3, and *17) genotype were collected. Here, we examined whether [(13) C]-pantoprazole exhibits enantioselective pharmacokinetics and whether this enantioselectivity is correlated with indices of breath test.

Methods: Plasma (-)- and (+)-[(13) C]-pantoprazole that were measured using a chiral HPLC were compared between CYP2C19 genotypes and correlated with breath test indices.

Results: The AUC( 0-∞) of (+)-[(13) C]-pantoprazole in PM (*2/*2, n = 4) was 10.1- and 5.6-fold higher that EM (*1/*1or *17, n = 10) and IM (*1/*2or *3, n = 10) of CYP2C19, respectively (P < 0.001). The AUC( 0-∞) of (-)-[(13) C]-pantoprazole only significantly differed between PMs and EMs (1.98-fold; P = 0.05). The AUC( 0-∞) ratio of (+)-/(-)-[(13) C]-pantoprazole was 3.45, 0.77, and 0.67 in PM, IM, and EM genotypes, respectively. Breath test index, delta over baseline show significant correlation with AUC( 0-∞) of (+)-[(13) C]-pantoprazole (Pearson's r = 0.62; P < 0.001).

Conclusions: [(13) C]-pantoprazole exhibits enantioselective elimination. (+)-[(13) C]-pantoprazole is more dependent on CYP2C19 metabolic status and may serve as a more attractive probe of CYP2C19 activity than (-)-[(13) C]-pantoprazole or the racemic mixture.

Keywords: breath test; genotype; pharmacokinetics; racemic.

Publication types

  • Clinical Trial
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Pyridinylmethylsulfinylbenzimidazoles / chemistry*
  • 2-Pyridinylmethylsulfinylbenzimidazoles / metabolism
  • 2-Pyridinylmethylsulfinylbenzimidazoles / pharmacokinetics*
  • Adolescent
  • Adult
  • Breath Tests
  • Carbon Isotopes / chemistry
  • Cytochrome P-450 CYP2C19 / metabolism*
  • Enzyme Assays / methods*
  • Female
  • Humans
  • Male
  • Middle Aged
  • Pantoprazole
  • Phenotype*
  • Stereoisomerism
  • Substrate Specificity
  • Young Adult

Substances

  • 2-Pyridinylmethylsulfinylbenzimidazoles
  • Carbon Isotopes
  • Pantoprazole
  • Cytochrome P-450 CYP2C19