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Volumn 82, Issue 2, 2012, Pages 302-309

Formation of the thiol conjugates and active metabolite of clopidogrel by human liver microsomes

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; CLOPIDOGREL; CYSTEINE; DITHIOTHREITOL; DRUG METABOLITE; GLUTATHIONE; THIOLACTONE;

EID: 84863907523     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.112.079061     Document Type: Article
Times cited : (24)

References (30)
  • 1
    • 54149112344 scopus 로고    scopus 로고
    • Interaction of the active metabolite of prasugrel, R-138727, with cysteine 97 and cysteine 175 of the human P2Y12 receptor
    • Algaier I, Jakubowski JA, Asai F, and von Kügelgen I (2008) Interaction of the active metabolite of prasugrel, R-138727, with cysteine 97 and cysteine 175 of the human P2Y12 receptor. J Thromb Haemost 6:1908-1914.
    • (2008) J Thromb Haemost , vol.6 , pp. 1908-1914
    • Algaier, I.1    Jakubowski, J.A.2    Asai, F.3    Von Kügelgen, I.4
  • 4
    • 62249112083 scopus 로고    scopus 로고
    • Metabolic oxidative cleavage of thioesters: Evidence for the formation of sulfenic acid intermediates in the bioactivation of the antithrombotic prodrugs ticlopidine and clopidogrel
    • Dansette PM, Libraire J, Bertho G, and 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 22:369-373.
    • (2009) Chem Res Toxicol , vol.22 , pp. 369-373
    • Dansette, P.M.1    Libraire, J.2    Bertho, G.3    Mansuy, D.4
  • 5
    • 80052497112 scopus 로고    scopus 로고
    • Paraoxonase-1 and clopidogrel efficacy
    • Dansette PM, Rosi J, Bertho G, and Mansuy D (2011) Paraoxonase-1 and clopidogrel efficacy. Nat Med 17:1040-1041.
    • (2011) Nat Med , vol.17 , pp. 1040-1041
    • Dansette, P.M.1    Rosi, J.2    Bertho, G.3    Mansuy, D.4
  • 6
    • 84859747728 scopus 로고    scopus 로고
    • Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer
    • Dansette PM, Rosi J, Bertho G, and Mansuy D (2012) Cytochromes P450 catalyze both steps of the major pathway of clopidogrel bioactivation, whereas paraoxonase catalyzes the formation of a minor thiol metabolite isomer. Chem Res Toxicol 25:348-356.
    • (2012) Chem Res Toxicol , vol.25 , pp. 348-356
    • Dansette, P.M.1    Rosi, J.2    Bertho, G.3    Mansuy, D.4
  • 7
    • 0037588974 scopus 로고    scopus 로고
    • Inactivation of the human P2Y12 receptor by thiol reagents requires interaction with both extracellular cysteine residues, Cys17 and Cys270
    • Ding Z, Kim S, Dorsam RT, Jin J, and Kunapuli SP (2003) Inactivation of the human P2Y12 receptor by thiol reagents requires interaction with both extracellular cysteine residues, Cys17 and Cys270. Blood 101:3908-3914.
    • (2003) Blood , vol.101 , pp. 3908-3914
    • Ding, Z.1    Kim, S.2    Dorsam, R.T.3    Jin, J.4    Kunapuli, S.P.5
  • 8
    • 0042859862 scopus 로고    scopus 로고
    • Adenosine diphosphate-induced platelet aggregation is associated with P2Y12 gene sequence variations in healthy subjects
    • Fontana P, Dupont A, Gandrille S, Bachelot-Loza C, Reny JL, Aiach M, and Gaussem P (2003) Adenosine diphosphate-induced platelet aggregation is associated with P2Y12 gene sequence variations in healthy subjects. Circulation 108:989-995.
    • (2003) Circulation , vol.108 , pp. 989-995
    • Fontana, P.1    Dupont, A.2    Gandrille, S.3    Bachelot-Loza, C.4    Reny, J.L.5    Aiach, M.6    Gaussem, P.7
  • 9
    • 77955510224 scopus 로고
    • Oxidation-reduction potentials of ascorbic acid
    • Fruton JS (1934) Oxidation-reduction potentials of ascorbic acid. J Biol Chem 105:79-85.
    • (1934) J Biol Chem , vol.105 , pp. 79-85
    • Fruton, J.S.1
  • 10
    • 79251528235 scopus 로고    scopus 로고
    • Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel
    • Hagihara K, Kazui M, Kurihara A, Kubota K, and Ikeda T (2011) Glutaredoxin and thioredoxin can be involved in producing the pharmacologically active metabolite of a thienopyridine antiplatelet agent, prasugrel. Drug Metab Dispos 39:208-214.
    • (2011) Drug Metab Dispos , vol.39 , pp. 208-214
    • Hagihara, K.1    Kazui, M.2    Kurihara, A.3    Kubota, K.4    Ikeda, T.5
  • 11
    • 0023066152 scopus 로고
    • Measurement of thiol-disulfide inter-change reactions and thiol pKa values
    • Houk J, Singh R, and Whitesides GM (1987) Measurement of thiol-disulfide inter-change reactions and thiol pKa values. Methods Enzymol 143:129-140.
    • (1987) Methods Enzymol , vol.143 , pp. 129-140
    • Houk, J.1    Singh, R.2    Whitesides, G.M.3
  • 12
    • 33749339075 scopus 로고    scopus 로고
    • Cytochrome P450 2C19 loss-of-function polymorphism is a major determinant of clopidogrel responsiveness in healthy subjects
    • Hulot JS, Bura A, Villard E, Azizi M, Remones V, Goyenvalle C, Aiach M, Lechat P, and Gaussem P (2006) Cytochrome P450 2C19 loss-of-function polymorphism is a major determinant of clopidogrel responsiveness in healthy subjects. Blood 108:2244-2247.
    • (2006) Blood , vol.108 , pp. 2244-2247
    • Hulot, J.S.1    Bura, A.2    Villard, E.3    Azizi, M.4    Remones, V.5    Goyenvalle, C.6    Aiach, M.7    Lechat, P.8    Gaussem, P.9
  • 13
    • 77953896604 scopus 로고    scopus 로고
    • Cardiovascular risk in clopidogrel-treated patients according to cytochrome P450 2C19*2 loss-of-function allele or proton pump inhibitor coadministration: A systematic meta-analysis
    • Hulot JS, Collet JP, Silvain J, Pena A, Bellemain-Appaix A, Barthélémy O, Cayla G, Beygui F, and Montalescot G (2010) Cardiovascular risk in clopidogrel-treated patients according to cytochrome P450 2C19*2 loss-of-function allele or proton pump inhibitor coadministration: a systematic meta-analysis. J Am Coll Cardiol 56:134-143.
    • (2010) J Am Coll Cardiol , vol.56 , pp. 134-143
    • Hulot, J.S.1    Collet, J.P.2    Silvain, J.3    Pena, A.4    Bellemain-Appaix, A.5    Barthélémy, O.6    Cayla, G.7    Beygui, F.8    Montalescot, G.9
  • 14
    • 0014139748 scopus 로고
    • The standard redox potential of cysteine-cystine from the thioldisulphide exchange reaction with glutathione and lipoic acid
    • Jocelyn PC (1967) The standard redox potential of cysteine-cystine from the thioldisulphide exchange reaction with glutathione and lipoic acid. Eur J Biochem 2:327-331.
    • (1967) Eur J Biochem , vol.2 , pp. 327-331
    • Jocelyn, P.C.1
  • 15
    • 73149119363 scopus 로고    scopus 로고
    • Identification of the human cytochrome P450 enzymes involved in the two oxidative steps in the bioactivation of clopidogrel to its pharmacologically active metabolite
    • Kazui M, Nishiya Y, Ishizuka T, Hagihara K, Farid NA, Okazaki O, Ikeda T, and Kurihara A (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.
    • (2010) Drug Metab Dispos , vol.38 , pp. 92-99
    • Kazui, M.1    Nishiya, Y.2    Ishizuka, T.3    Hagihara, K.4    Farid, N.A.5    Okazaki, O.6    Ikeda, T.7    Kurihara, A.8
  • 18
    • 78049326068 scopus 로고    scopus 로고
    • Reduced-function CYP2C19 genotype and risk of adverse clinical outcomes among patients treated with clopidogrel predominantly for PCI: A meta-analysis
    • Mega JL, Simon T, Collet JP, Anderson JL, Antman EM, Bliden K, Cannon CP, Danchin N, Giusti B, Gurbel P, et al. (2010) Reduced-function CYP2C19 genotype and risk of adverse clinical outcomes among patients treated with clopidogrel predominantly for PCI: a meta-analysis. JAMA 304:1821-1830.
    • (2010) JAMA , vol.304 , pp. 1821-1830
    • Mega, J.L.1    Simon, T.2    Collet, J.P.3    Anderson, J.L.4    Antman, E.M.5    Bliden, K.6    Cannon, C.P.7    Danchin, N.8    Giusti, B.9    Gurbel, P.10
  • 20
    • 0034212604 scopus 로고    scopus 로고
    • Population, acid-base, and redox properties of N-acetylcysteine conformers
    • Noszál B, Visky D, and Kraszni M (2000) Population, acid-base, and redox properties of N-acetylcysteine conformers. J Med Chem 43:2176-2182.
    • (2000) J Med Chem , vol.43 , pp. 2176-2182
    • Noszál, B.1    Visky, D.2    Kraszni, M.3
  • 25
    • 79960603688 scopus 로고    scopus 로고
    • Genetic polymorphisms and the impact of a higher clopidogrel dose regimen on active metabolite exposure and antiplatelet response in healthy subjects
    • Simon T, Bhatt DL, Bergougnan L, Farenc C, Pearson K, Perrin L, Vicaut E, Lacreta F, Hurbin F, and Dubar M (2011) Genetic polymorphisms and the impact of a higher clopidogrel dose regimen on active metabolite exposure and antiplatelet response in healthy subjects. Clin Pharmacol Ther 90:287-295.
    • (2011) Clin Pharmacol Ther , vol.90 , pp. 287-295
    • Simon, T.1    Bhatt, D.L.2    Bergougnan, L.3    Farenc, C.4    Pearson, K.5    Perrin, L.6    Vicaut, E.7    Lacreta, F.8    Hurbin, F.9    Dubar, M.10
  • 26
    • 33744968214 scopus 로고    scopus 로고
    • Increased risk of atherothrombotic events associated with cytochrome P450 3A5 polymorphism in patients taking clopidogrel
    • Suh JW, Koo BK, Zhang SY, Park KW, Cho JY, Jang IJ, Lee DS, Sohn DW, Lee MM, and Kim HS (2006) Increased risk of atherothrombotic events associated with cytochrome P450 3A5 polymorphism in patients taking clopidogrel. CMAJ 174:1715-1722.
    • (2006) CMAJ , vol.174 , pp. 1715-1722
    • Suh, J.W.1    Koo, B.K.2    Zhang, S.Y.3    Park, K.W.4    Cho, J.Y.5    Jang, I.J.6    Lee, D.S.7    Sohn, D.W.8    Lee, M.M.9    Kim, H.S.10
  • 27
    • 57849099154 scopus 로고    scopus 로고
    • Quantitative determination of clopidogrel active metabolite in human plasma by LC-MS/MS
    • Takahashi M, Pang H, Kawabata K, Farid NA, and Kurihara A (2008) Quantitative determination of clopidogrel active metabolite in human plasma by LC-MS/MS. J Pharm Biomed Anal 48:1219-1224.
    • (2008) J Pharm Biomed Anal , vol.48 , pp. 1219-1224
    • Takahashi, M.1    Pang, H.2    Kawabata, K.3    Farid, N.A.4    Kurihara, A.5
  • 30
    • 80054782748 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human cytochrome P450 2B6 by clopidogrel: Involvement of both covalent modification of cysteinyl residue 475 and loss of heme
    • Zhang H, Amunugama H, Ney S, Cooper N, and Hollenberg PF (2011) Mechanism-based inactivation of human cytochrome P450 2B6 by clopidogrel: involvement of both covalent modification of cysteinyl residue 475 and loss of heme. Mol Pharmacol 80:839-847.
    • (2011) Mol Pharmacol , vol.80 , pp. 839-847
    • Zhang, H.1    Amunugama, H.2    Ney, S.3    Cooper, N.4    Hollenberg, P.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.