Comparison of mechanism-based inhibition of human cytochrome P450 2C19 by ticlopidine, clopidogrel, and prasugrel

References

• Brandt JT, Payne CD, Wiviott SD, Weerakkody GJ, Farid NA, Small DS, Jakubowski JA, Naganuma H, Winters KJ. 2007. A comparison of prasugrel and clopidogrel loading doses on platelet function: magnitude of platelet inhibition is related to active metabolite formation. Am Heart J 153:66.e9–16.
   PubMed Web of Science ®Google Scholar
• Dansette PM, Libraire J, Bertho G, Mansuy D. 2009. Metabolic oxidative cleavage of thioesters: evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel. Chem Res Toxicol 22:369–73.
   PubMed Web of Science ®Google Scholar
• Farid NA, Smith RL, Gillespie TA, Rash TJ, Blair PE, Kurihara A, Goldberg MJ. 2007. The disposition of prasugrel, a novel thienopyridine, in humans. Drug Metab Dispos 35:1096–104.
   PubMed Web of Science ®Google Scholar
• Ghanbari F, Rowland-Yeo K, Bloomer JC, Clarke SE, Lennard MS, Tucker GT, Rostami-Hodjegan A. 2006. A critical evaluation of the experimental design of studies of mechanism based enzyme inhibition, with implications for in vitro–in vivo extrapolation. Curr Drug Metab 7:315–34.
   PubMed Web of Science ®Google Scholar
• Grimm SW, Einolf HJ, Hall SD, He K, Lim HK, Ling KHJ, Lu C, Nomeir AA, Seibert E, Skordos KW, Tonn GR, Horn RV, Wang RW, Wang YN, Yang TJ, Obach RS. 2009. The conduct of in vitro studies to address time-dependent inhibition of drug-metabolizing enzymes: a perspective of the Pharmaceutical Research and Manufacturers of America. Drug Metab Dispos 37:1355–70.
   PubMed Web of Science ®Google Scholar
• Ha-Duong NT, Dijols S, Macherey AC, Goldstein JA, Dansette PM Mansuy D. 2001. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40:12112–22.
   PubMed Web of Science ®Google Scholar
• Hagihara K, Nishiya Y, Kurihara A, Kazui M, Farid NA, Ikeda T. 2008. Comparison of human cytochrome P450 inhibition by the thienopyridines prasugrel, clopidogrel and ticlopidine. Drug Metab Pharmacokinet 23:412–20.
   PubMed Web of Science ®Google Scholar
• Ieiri I, Kimura M, Irie S, Urae A, Otsubo K, Ishizaki T. 2005. Interaction magnitude, pharmacokinetics and pharmacodynamics of ticlopidine in relation to CYP2C19 genotypic status. Pharmacogenet Genom 15:851–9.
   PubMed Web of Science ®Google Scholar
• Ko JW, Desta Z, Soukhova NV, Tracy T, Flockhart DA. 2000. In vitro inhibition of the cytochrome P450 (CYP450) system by the antiplatelet drug ticlopidine: potent effect on CYP2C19 and CYP2D6. Br J Clin Pharmacol 49:343–51.
   PubMed Web of Science ®Google Scholar
• Kurihara A, Hagihara K, Kazui M, Ozeki T, Farid NA, Ikeda T. 2005. In vitro metabolism of antiplatelet agent clopidogrel: cytochrome P450 isoforms responsible for two oxidation steps involved in the active metabolite formation. Drug Metab Rev Suppl (2):99.
   Google Scholar
• Li XQ, Weidolf L, Simonsson R, Andersson TB. 2005. Enantiomer/enantiomer interactions between the S- and R-isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther 315:777–87.
   PubMed Web of Science ®Google Scholar
• Mayhew BS, Jones DR. Hall SD. 2000. An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos 28:1031–7.
   PubMed Web of Science ®Google Scholar
• Mega JL, Close SL, Wiviott SD, Shen L, Hockett RD, Brandt JT, Walker JR, Antman EM, Macias W, Braunwald E, Sabatine MS. 2009. Cytochrome P-450 polymorphisms and response to clopidogrel. N Engl J Med 360:354–62.
   PubMed Web of Science ®Google Scholar
• Niitsu Y, Jakubowski JA, Sugidachi A, Asai F. 2005. Pharmacology of CS-747 (Prasugrel, LY640315), a novel, potent antiplatelet agent with in vivo P2Y12 receptor antagonist activity. Semin Thromb Hemost 31:184–94.
   PubMed Web of Science ®Google Scholar
• Nirogi RVS, Kandikere VN, Shukla K, Mudigonda K, Maurya S, Boosi R. 2006. Quantification of clopidogrel in human plasma by sensitive liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 20:1695–700.
   PubMed Web of Science ®Google Scholar
• Nishiya Y., Hagihara K, Ito T, Tajima M, Miura S, Kurihara A, Farid NA, Ikeda T. 2009. Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrel. Drug Metab Dispos 37:589–93.
   PubMed Web of Science ®Google Scholar
• Obach RS, Walsky RL, Venkatakrishnan K. 2007. Mechanism-based inactivation of human cytochrome P450 enzymes and the prediction of drug–drug interactions. Drug Metab Dispos 35:246–55.
   PubMed Web of Science ®Google Scholar
• Rehmel JLF, Eckstein JA, Farid NA, Heim JB, Kasper SC, Kurihara A, Wrighton SA, Ring BJ. 2006. Interactions of two major metabolites of prasugrel, a thienopyridine antiplatelet agent, with the cytochromes P450. Drug Metab Dispos 34:600–7.
   PubMed Web of Science ®Google Scholar
• Sharis PJ, Cannon CP, Loscalzo J. 1998. The antiplatelet effects of ticlopidine and clopidogrel. Ann Intern Med 129:394–405.
   PubMed Web of Science ®Google Scholar
• Silverman RB. 1988. The potential use of mechanism-based enzyme inactivators in medicine. J Enzyme Inhib 2:73–90.
   PubMedGoogle Scholar
• Turpeinen M, Nieminen R, Juntunen T, Taavitsainen P, Raunio H, Pelkonen O. 2004. Selective inhibition of CYP2B6-catalyzed bupropion hydroxylation in human liver microsomes in vitro. Drug Metab Dispos 32:626–31.
   PubMed Web of Science ®Google Scholar
• Venkatakrishnan K, Obach RS. 2005. In vitro–in vivo extrapolation of CYP2D6 inactivation by paroxetine: prediction of nonstationary pharmacokinetics and drug interaction magnitude. Drug Metab Dispos 33:845–52.
   PubMed Web of Science ®Google Scholar
• Walsky RL, Astuccio AV, Obach RS. 2006. Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol 46:1426–38.
   PubMed Web of Science ®Google Scholar
• Wang YH, Jones DR, Hall SD. 2004. Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos 32:259–66.
   PubMed Web of Science ®Google Scholar
• Williams ET, Jones KO, Ponsler GD, Lowery SM, Perkins EJ, Wrighton SA, Ruterbories KJ, Kazui M, Farid NA. 2008. The biotransformation of prasugrel, a new thienopyridine prodrug, by the human carboxylesterases 1 and 2. Drug Metab Dispos 36:1227–32.
   PubMed Web of Science ®Google Scholar
• Wiviott SD, Braunwald E, McCabe CH, Montalescot G, Ruzyllo W, Gottlieb S, Neumann FJ, Ardissino D, De Servi S, Murphy SA, Riesmeyer J, Weerakkody G, Gibson CM, Antman EM. 2007. Prasugrel versus clopidogrel in patients with acute coronary syndromes. N Engl J Med 357:2001–15.
   PubMed Web of Science ®Google Scholar
• Yoneda K, Iwamura R, Kishi H, Mizukami Y, Mogami K, Kobayashi S. 2004. Identification of the active metabolite of ticlopidine from rat in vitro metabolites. Br J Pharmacol 142:551–7.
   PubMed Web of Science ®Google Scholar
• Yuan R, Madani S, Wei X-X, Reynolds K, Huang S-M. 2002. Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab Dispos 30:1311–19.
   PubMed Web of Science ®Google Scholar