A comparison of the metabolism of clopidogrel and prasugrel

Bibliography

• Brandt JT, Payne CD, Wiviott SD, A comparison of prasugrel and clopidogrel loading doses on platelet function: magnitude of platelet inhibition is related to active metabolite formation. Am Heart J 2007;153(1):66 e9-16
   PubMedGoogle Scholar
• Sugidachi A, Ogawa T, Kurihara A, The greater in vivo antiplatelet effects of prasugrel as compared to clopidogrel reflect more efficient generation of its active metabolite with similar antiplatelet activity to that of clopidogrel's active metabolite. J Thromb Haemost 2007;5(7):1545-51
   PubMed Web of Science ®Google Scholar
• Kazui M, Nishiya Y, Ishizuka T, Identification of the human cytochrome P450 enzymes involved in the two oxidative steps in the bioactivation of clopidogrel to its pharmacologically active metabolite. Drug Metab Dispos 2010;38(1):92-9
   PubMed Web of Science ®Google Scholar
• Farid NA, Kurihara A, Wrighton SA. Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans. J Clin Pharmacol 2010;50(2):126-42
   PubMed Web of Science ®Google Scholar
• Farid NA, Smith RL, Gillespie TA, The disposition of prasugrel, a novel thienopyridine, in humans. Drug Metab Dispos 2007;35(7):1096-104
   PubMed Web of Science ®Google Scholar
• Sofi F, Giusti B, Marcucci R, Cytochrome P450 2C19(*)2 polymorphism and cardiovascular recurrences in patients taking clopidogrel: a meta-analysis. Pharmacogenomics J 2010 Mar 30 [Epub ahead of print]
   Google Scholar
• Mega JL, Close SL, Wiviott SD, Cytochrome p-450 polymorphisms and response to clopidogrel. N Engl J Med 2009;360(4):354-62
   PubMed Web of Science ®Google Scholar
• Harmsze A, van Werkum JW, Bouman HJ, Besides CYP2C19*2, the variant allele CYP2C9*3 is associated with higher on-clopidogrel platelet reactivity in patients on dual antiplatelet therapy undergoing elective coronary stent implantation. Pharmacogenet Genomics 2010;20(1):18-25
   PubMed Web of Science ®Google Scholar
• Hagihara K, Kazui M, Ikenaga H, Comparison of formation of thiolactones and active metabolites of prasugrel and clopidogrel in rats and dogs. Xenobiotica 2009;39(3):218-26
   PubMed Web of Science ®Google Scholar
• Sofi F, Marcucci R, Gori AM, Clopidogrel non-responsiveness and risk of cardiovascular morbidity. An updated meta-analysis. Thromb Haemost 2010;103(4):841-8
   PubMed Web of Science ®Google Scholar
• Hagihara K, Kazui M, Kurihara A, A possible mechanism for the differences in efficiency and variability of active metabolite formation from thienopyridine antiplatelet agents, prasugrel and clopidogrel. Drug Metab Dispos 2009;37(11):2145-52
   PubMed Web of Science ®Google Scholar
• Umemura K, Furuta T, Kondo K. The common gene variants of CYP2C19 affect pharmacokinetics and pharmacodynamics in an active metabolite of clopidogrel in healthy subjects. J Thromb Haemost 2008;6(8):1439-41
   PubMed Web of Science ®Google Scholar
• Brandt JT, Close SL, Iturria SJ, Common polymorphisms of CYP2C19 and CYP2C9 affect the pharmacokinetic and pharmacodynamic response to clopidogrel but not prasugrel. J Thromb Haemost 2007;5(12):2429-36
   PubMed Web of Science ®Google Scholar
• Mega JL, Close SL, Wiviott SD, Cytochrome P450 genetic polymorphisms and the response to prasugrel: relationship to pharmacokinetic, pharmacodynamic, and clinical outcomes. Circulation 2009;119(19):2553-60
   PubMed Web of Science ®Google Scholar
• Holmes DR Jr, Dehmer GJ, Kaul S, ACCF/AHA clopidogrel clinical alert: approaches to the FDA “Boxed Warning”. A Report of the American College of Cardiology Foundation Task Force on Clinical Expert Consensus Documents and the American Heart Association. Circulation 2010;56(4):321-41
   Google Scholar
• Shuldiner AR, O'Connell JR, Bliden KP, Association of cytochrome P450 2C19 genotype with the antiplatelet effect and clinical efficacy of clopidogrel therapy. JAMA 2009;302(8):849-57
   PubMed Web of Science ®Google Scholar
• Collet JP, Hulot JS, Pena A, Cytochrome P450 2C19 polymorphism in young patients treated with clopidogrel after myocardial infarction: a cohort study. Lancet 2009;373(9660):309-17
   PubMed Web of Science ®Google Scholar
• Bhatt DL, Scheiman J, Abraham NS, ACCF/ACG/AHA 2008 expert consensus document on reducing the gastrointestinal risks of antiplatelet therapy and NSAID use: a report of the American College of Cardiology Foundation Task Force on Clinical Expert Consensus Documents. Circulation 2008;118(18):1894-909
   PubMed Web of Science ®Google Scholar
• Ho PM, Maddox TM, Wang L, Risk of adverse outcomes associated with concomitant use of clopidogrel and proton pump inhibitors following acute coronary syndrome. JAMA 2009;301(9):937-44
   PubMed Web of Science ®Google Scholar
• Juurlink DN, Gomes T, Ko DT, A population-based study of the drug interaction between proton pump inhibitors and clopidogrel. CMAJ 2009;180(7):713-18
   PubMed Web of Science ®Google Scholar
• Bliden KP, Dichiara J, Lawal L, The association of cigarette smoking with enhanced platelet inhibition by clopidogrel. J Am Coll Cardiol 2008;52(7):531-3
   PubMed Web of Science ®Google Scholar
• Small DS, Farid NA, Payne CD, Effects of the proton pump inhibitor lansoprazole on the pharmacokinetics and pharmacodynamics of prasugrel and clopidogrel. J Clin Pharmacol 2008;48(4):475-84
   PubMed Web of Science ®Google Scholar
• Lee JM, Park S, Shin DJ, Relation of genetic polymorphisms in the cytochrome P450 gene with clopidogrel resistance after drug-eluting stent implantation in Koreans. Am J Cardiol 2009;104(1):46-51
   PubMed Web of Science ®Google Scholar
• Caplain H, Donat F, Gaud C, Pharmacokinetics of clopidogrel. Semin Thromb Hemost 1999;25(Suppl 2):25-8
   PubMed Web of Science ®Google Scholar
• Taketani M, Shii M, Ohura K, Carboxylesterase in the liver and small intestine of experimental animals and human. Life Sci 2007;81(11):924-32
   PubMed Web of Science ®Google Scholar
• Williams ET, Jones KO, Ponsler GD, The biotransformation of prasugrel, a new thienopyridine prodrug, by the human carboxylesterases 1 and 2. Drug Metab Dispos 2008;36(7):1227-32
   PubMed Web of Science ®Google Scholar
• Ross MK, Crow JA. Human carboxylesterases and their role in xenobiotic and endobiotic metabolism. J Biochem Mol Toxicol 2007;21(4):187-96
   PubMed Web of Science ®Google Scholar
• Siller-Matula JM, Krumphuber J, Jilma B. Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases. Br J Pharmacol 2010;159(3):502-17
   PubMed Web of Science ®Google Scholar
• Wiviott SD, Trenk D, Frelinger AL, Prasugrel compared with high loading- and maintenance-dose clopidogrel in patients with planned percutaneous coronary intervention: the Prasugrel in Comparison to Clopidogrel for Inhibition of Platelet Activation and Aggregation-Thrombolysis in Myocardial Infarction 44 trial. Circulation 2007;116(25):2923-32
   PubMed Web of Science ®Google Scholar
• Farid NA, Payne CD, Small DS, Cytochrome P450 3A inhibition by ketoconazole affects prasugrel and clopidogrel pharmacokinetics and pharmacodynamics differently. Clin Pharmacol Ther 2007;81(5):735-41
   PubMed Web of Science ®Google Scholar
• Jakubowski JA, Payne CD, Brandt JT, The platelet inhibitory effects and pharmacokinetics of prasugrel after administration of loading and maintenance doses in healthy subjects. J Cardiovasc Pharmacol 2006;47(3):377-84
   PubMed Web of Science ®Google Scholar
• Wiviott SD, Braunwald E, McCabe CH, Prasugrel versus clopidogrel in patients with acute coronary syndromes. N Engl J Med 2007;357(20):2001-15
   PubMed Web of Science ®Google Scholar
• Morrow DA, Wiviott SD, White HD, Effect of the novel thienopyridine prasugrel compared with clopidogrel on spontaneous and procedural myocardial infarction in the Trial to Assess Improvement in Therapeutic Outcomes by Optimizing Platelet Inhibition with Prasugrel-Thrombolysis in Myocardial Infarction 38: an application of the classification system from the universal definition of myocardial infarction. Circulation 2009;119(21):2758-64
   PubMed Web of Science ®Google Scholar
• Wiviott SD, Antman EM, Winters KJ, Randomized comparison of prasugrel (CS-747, LY640315), a novel thienopyridine P2Y12 antagonist, with clopidogrel in percutaneous coronary intervention: results of the Joint Utilization of Medications to Block Platelets Optimally (JUMBO)-TIMI 26 trial. Circulation 2005;111(25):3366-73
   PubMed Web of Science ®Google Scholar
• Zhu HJ, Patrick KS, Yuan HJ, Two CES1 gene mutations lead to dysfunctional carboxylesterase 1 activity in man: clinical significance and molecular basis. Am J Hum Genet 2008;82(6):1241-8
   PubMed Web of Science ®Google Scholar
• Shi D, Yang J, Yang D, Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 2006;319(3):1477-84
   PubMed Web of Science ®Google Scholar
• Bailey DN, Briggs JR. Procainamide and quinidine inhibition of the human hepatic degradation of meperidine in vitro. J Anal Toxicol 2003;27(3):142-4
   PubMed Web of Science ®Google Scholar
• Zhu HJ, Appel DI, Peterson YK, Identification of selected therapeutic agents as inhibitors of carboxylesterase 1: potential sources of metabolic drug interactions. Toxicology 2010;270(2-3):59-65
   PubMed Web of Science ®Google Scholar
• Patrick KS, Straughn AB, Minhinnett RR, Influence of ethanol and gender on methylphenidate pharmacokinetics and pharmacodynamics. Clin Pharmacol Ther 2007;81(3):346-53
   PubMed Web of Science ®Google Scholar
• Laizure SC, Mandrell T, Gades NM, Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases. Drug Metab Dispos 2003;31(1):16-20
   PubMed Web of Science ®Google Scholar
• Parker RB, Laizure SC. The effect of ethanol on oral cocaine pharmacokinetics reveals an unrecognized class of ethanol-mediated drug interactions. Drug Metab Dispos 2010;38(2):317-22
   PubMed Web of Science ®Google Scholar
• Roberts SM, Harbison RD, James RC. Inhibition by ethanol of the metabolism of cocaine to benzoylecgonine and ecgonine methyl ester in mouse and human liver. Drug Metab Dispos 1993;21(3):537-41
   PubMed Web of Science ®Google Scholar
• Kubo T, Kim SR, Sai K, Functional characterization of three naturally occurring single nucleotide polymorphisms in the CES2 gene encoding carboxylesterase 2 (HCE-2). Drug Metab Dispos 2005;33(10):1482-7
   PubMed Web of Science ®Google Scholar
• Kim SR, Sai K, Tanaka-Kagawa T, Haplotypes and a novel defective allele of CES2 found in a Japanese population. Drug Metab Dispos 2007;35(10):1865-72
   PubMed Web of Science ®Google Scholar
• Charasson V, Haaz MC, Robert J. Determination of drug interactions occurring with the metabolic pathways of irinotecan. Drug Metab Dispos 2002;30(6):731-3
   PubMed Web of Science ®Google Scholar
• Cundy KC, Annamalai T, Bu L, XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: II. Improved oral bioavailability, dose proportionality, and colonic absorption compared with gabapentin in rats and monkeys. J Pharmacol Exp Ther 2004;311(1):324-33
   PubMed Web of Science ®Google Scholar
• Choppin A, Irwin I, Lach L, Effect of tecarfarin, a novel vitamin K epoxide reductase inhibitor, on coagulation in beagle dogs. Br J Pharmacol 2009;158(6):1536-47
   PubMed Web of Science ®Google Scholar