The mechanism and risk factors of clopidogrel-induced liver injury

References

• Beltran-Robles M, Marquez Saavedra E, Sanchez-Muñoz D, Romero-Gomez M. (2004). Hepatotoxicity induced by clopidogrel. J Hepatol 40:560–562
   PubMed Web of Science ®Google Scholar
• Bertrand ME, Rupprecht HJ, Urban P. (2000). Double-blind study of the safety of clopidogrel with and without a loading dose in combination with aspirin compared with ticlopidine in combination with aspirin after coronary stenting: the clopidogrel aspirin stent international cooperative study. Cirulation 102:624–629
   PubMed Web of Science ®Google Scholar
• Dansette PM, Levent D, Hessani A, et al. (2013). Thiolactone sulfoxides as new reactive metabolites acting as bis-electrophiles: implication in clopidogrel and prasugrel bioactivation. Chem Res Toxicol 26:794–802
   PubMed Web of Science ®Google Scholar
• Dansette PM, Levent D, Hessani A, Mansuy D. (2015). Bioactivation of clopidogrel and prasugrel: factors determining the stereochemistry of the thiol metabolite double bond. Chem Res Toxicol 28:1338–1345
   PubMed Web of Science ®Google Scholar
• Farid NA, Kurihara A, Wrighton SA. (2010). Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans. J Clin Pharmacol 50:126–142
   PubMed Web of Science ®Google Scholar
• Fontana E, Dansette PM, Poli SM. (2005). Cytochrome P450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metabol 6:413–454
   PubMed Web of Science ®Google Scholar
• Goyal RK, Srivastava D, Lessnau KD. (2009). Clopidogrel-induced hepatocellular injury and cholestatic jaundice in an elderly patient: case report and review of the literature. Pharmacotherapy 29:608–612
   PubMed Web of Science ®Google Scholar
• Huijzer JC, Adams JD, Jaw JY. (1989). Inhibition of 3-methylindole bioactivation by the cytochrome P-450 suicide substrates 1-aminobenzotriazole and alpha-methylbenzylaminobenzotriazole. Drug Metab Dispos 17:37–42
   PubMed Web of Science ®Google Scholar
• Kazui M, Nishiya Y, Ishizuka T. (2010). 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 38:92–99
   PubMed Web of Science ®Google Scholar
• Knowles SR, Uetrecht J, Shear NH. (2000). Idiosyncratic drug reactions: the reactive metabolite syndromes. Lancet 356:1587–1591
   PubMed Web of Science ®Google Scholar
• Kohriyama T, Mihara C, Yokoyama T. (2014). Safety evaluation of substituting clopidogrel for ticlopidine in Japanese patients with ischemic stroke-Hiroshima ticlopidine, clopidogrel safe exchange trial. J Stroke Cerebrovasc Dis 23:1485–1490
   PubMed Web of Science ®Google Scholar
• Lammert C, Bjornsson E, Niklasson A. (2010). Oral medications with significant hepatic metabolism at higher risk for hepatic adverse events. Hepatology 51:615–620
   PubMed Web of Science ®Google Scholar
• Liu C, Chen Z, Zhong K, et al. (2015). Human liver cytochrome P450 enzymes and microsomal thiol methyltransferase are involved in the stereoselective formation and methylation of the pharmacologically active metabolite of clopidogrel. Drug Metab Dispos 43:1632–1641
   PubMed Web of Science ®Google Scholar
• Maseneni S, Donzelli M, Taegtmeyer AB. (2012). Toxicity of clopidogrel and ticlopidine on human myeloid progenitor cells: importance of metabolites. Toxicology 299:139–145
   PubMed Web of Science ®Google Scholar
• Mugford CA, Mortillo M, Mico BA. (1992). 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats. Fundam Appl Toxicol 19:43–49
   PubMedGoogle Scholar
• Ng JA, Goldberg N, Tafreshi MJ. (2006). Clopidogrel-induced hepatotoxicity and fever. Pharmacotherapy 26:1023–1026
   PubMed Web of Science ®Google Scholar
• Porto I, Giubilato S, De Maria GL. (2009). Platelet P2Y12 receptor inhibition by thienopyridines: status and future. Expert Opin Investig Drugs 18:1317–1332
   PubMed Web of Science ®Google Scholar
• Sangkuhl K, Klein TE, Altman RB. (2010). Clopidogrel pathway. Pharmacogenet Genomics 20:463–465
   PubMed Web of Science ®Google Scholar
• Sasaki E, Matsuo K, Iida A. (2013). A novel mouse model for phenytoin-induced liver injury: involvement of immune-related factors and P450-mediated metabolism. Toxicol Sci 136:250–263
   PubMed Web of Science ®Google Scholar
• Shaw SA, Balasubramanian B, Bonacorsi S, et al. (2015). Synthesis of biologically active piperidine metabolites of clopidogrel: determination of structure and analyte development. J Org Chem 80:7019–7032
   PubMed Web of Science ®Google Scholar
• Seglen PO. (1976). Preparation of isolated rat liver cells. Methods Cell Biol 13:29–83
   PubMedGoogle Scholar
• Sharis PJ, Cannon CP, Loscalzo J. (1988). The antiplatelet effects of ticlopidine and clopidogrel. Ann Intern Med 129:394–405
   Google Scholar
• Shimizu S, Atsumi R, Nakazawa T. (2011). Ticlopidine-induced hepatotoxicity in a GSH-depleted rat model. Arch Toxicol 85:347–53
   PubMed Web of Science ®Google Scholar
• Smiley ST, Reers M, Mottola-Hartshorn C, et al. (2011). Ticlopidine-induced hepatotoxicity in a GSH-depleted rat model. Arch Toxicol 85:347–353
   PubMed Web of Science ®Google Scholar
• Tang M, Mukundan M, Yang J. (2006). Antiplatelet agents aspirin and clopidogrel are hydrolyzed by distinct carboxylesterases, and clopidogrel is transesterificated in the presence of ethyl alcohol. J Pharmacol Exp Ther 319:1467–1476
   PubMed Web of Science ®Google Scholar
• Van der Hoeven TA, Coon MJ. (1974). Preparation and properties of partially purified cytochrome P-450 and reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase from rabbit liver microsomes. J Biol Chem. 249:6302–6310
   PubMed Web of Science ®Google Scholar
• Watanabe T, Sagisaka H, Arakawa S. (2003). A novel model of continuous depletion of glutathione in mice treated with l-buthionine (S, R)-sulfoximine. J Toxicol Sci 28:455–463
   PubMedGoogle Scholar
• Zahno A, Brecht K, Bodmer M. (2010). Effects of drug interactions on biotransformation and antiplatelet effect of clopidogrel in vitro. Br J Pharmacol 161:393–404
   PubMed Web of Science ®Google Scholar
• Zahno A, Bouitbir J, Maseneni S. (2013). Hepatocellular toxicity of clopidogrel: mechanisms and risk factors. Free Radic Biol Med 65:208–216
   PubMed Web of Science ®Google Scholar
• Zeolla MM, Carson JJ. (1999). Successful use of clopidogrel for cerebrovascular accident in a patient with suspected ticlopidine-induced hepatotoxicity. Ann Pharmacother 33:939–941
   PubMed Web of Science ®Google Scholar
• Zhu HJ, Wang X, Gawronski BE. (2013). Carboxylesterase 1 as a determinant of clopidogrel metabolism and activation. J Pharmacol Exp Ther 344:665–672
   PubMed Web of Science ®Google Scholar
• Zhu Y, Zhou J. (2013). In vitro biotransformation studies of 2-oxo-clopidogrel: multiple thiolactone ring-opening pathways further attenuate prodrug activation. Chem Res Toxicol 26:179–190
   PubMed Web of Science ®Google Scholar
• Zhu Y, Zhou J. (2012). Identification of the significant involvement and mechanistic role of CYP3A4/5 in clopidogrel bioactivation. ACS Med Chem Lett 3:844–849
   PubMed Web of Science ®Google Scholar