메뉴 건너뛰기




Volumn 39, Issue 3, 2011, Pages 539-550

Comparison of in vitro metabolism of ticlopidine by human cytochrome P450 2B6 and rabbit cytochrome P450 2B4

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOTICLOPIDINE; 5 (2 CHLOROBENZYL)THIENO[3,2 C]PYRIDIN 5 IUM METABOLITE; 7 HYDROXYTICLOPIDINE; CYTOCHROME P450 2B4; CYTOCHROME P450 2B6; DRUG METABOLITE; THIOPHENE; TICLOPIDINE; TICLOPIDINE N OXIDE; TICLOPIDINE S OXIDE; UNCLASSIFIED DRUG;

EID: 79951873368     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.037101     Document Type: Article
Times cited : (22)

References (40)
  • 1
    • 18344376209 scopus 로고    scopus 로고
    • Do Fukui function maxima relate to sites of metabolism? A critical case study
    • Beck ME (2005) Do Fukui function maxima relate to sites of metabolism? A critical case study. J Chem Inf Model 45:273-282.
    • (2005) J Chem Inf Model , vol.45 , pp. 273-282
    • Beck, M.E.1
  • 2
    • 1642498326 scopus 로고    scopus 로고
    • Characterization of novel dihydrothienopyridinium and thienopyridinium metabolites of ticlopidine in vitro: Role of peroxidases, cytochromes P450, and monoamine oxidases
    • DOI 10.1124/dmd.32.1.49
    • Dalvie DK and O'Connell TN (2004) Characterization of novel dihydrothienopyridinium and thienopyridinium metabolites of ticlopidine in vitro: role of peroxidases, cytochromes P450, and monoamine oxidases. Drug Metab Dispos 32:49-57. (Pubitemid 38112535)
    • (2004) Drug Metabolism and Disposition , vol.32 , Issue.1 , pp. 49-57
    • Dalvie, D.K.1    O'Connell, T.N.2
  • 3
    • 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
  • 4
    • 75749102996 scopus 로고    scopus 로고
    • Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans
    • Farid NA, Kurihara A, and Wrighton SA (2010) Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans. J Clin Pharmacol 50:126-142.
    • (2010) J Clin Pharmacol , vol.50 , pp. 126-142
    • Farid, N.A.1    Kurihara, A.2    Wrighton, S.A.3
  • 6
    • 77956574058 scopus 로고    scopus 로고
    • Structural features of cytochromes P450 and ligands that affect drug metabolism as revealed by x-ray crystallography and NMR
    • Gay SC, Roberts AG, and Halpert JR (2010c) Structural features of cytochromes P450 and ligands that affect drug metabolism as revealed by x-ray crystallography and NMR. Future Med Chem 2:1451-1468.
    • (2010) Future Med Chem , vol.2 , pp. 1451-1468
    • Gay, S.C.1    Roberts, A.G.2    Halpert, J.R.3
  • 8
    • 66649125786 scopus 로고    scopus 로고
    • Crystal structures of cytochrome P450 2B4 in complex with the inhibitor 1-biphenyl-4-methyl-1H-imidazole: Ligand-induced structural response through alpha-helical repositioning
    • Gay SC, Sun L, Maekawa K, Halpert JR, and Stout CD (2009) Crystal structures of cytochrome P450 2B4 in complex with the inhibitor 1-biphenyl-4-methyl-1H-imidazole: ligand-induced structural response through alpha-helical repositioning. Biochemistry 48:4762-4771.
    • (2009) Biochemistry , vol.48 , pp. 4762-4771
    • Gay, S.C.1    Sun, L.2    Maekawa, K.3    Halpert, J.R.4    Stout, C.D.5
  • 9
    • 0031854723 scopus 로고    scopus 로고
    • Cholestatic hepatitis due to ticlopidine: Clinical and histological recovery after drug withdrawal. Case report and review of the literature
    • Grieco A, Vecchio FM, Greco AV, and Gasbarrini G (1998) Cholestatic hepatitis due to ticlopidine: clinical and histological recovery after drug withdrawal. Case report and review of the literature. Eur J Gastroenterol Hepatol 10:713-715. (Pubitemid 28383121)
    • (1998) European Journal of Gastroenterology and Hepatology , vol.10 , Issue.8 , pp. 713-715
    • Grieco, A.1    Vecchio, F.M.2    Greco, A.V.3    Gasbarrini, G.4
  • 10
    • 84892246340 scopus 로고    scopus 로고
    • Human cytochrome P450 enzymes
    • 3rd ed (Ortiz de Montellano PR ed), Plenum Press, New York
    • Guengrich FP (2005) Human cytochrome P450 enzymes, in Cytochromes P450: Structure, Mechanism and Biochemistry, 3rd ed (Ortiz de Montellano PR ed), pp 377-350, Plenum Press, New York.
    • (2005) Cytochromes P450: Structure, Mechanism and Biochemistry , pp. 377-1350
    • Guengrich, F.P.1
  • 11
    • 0035834052 scopus 로고    scopus 로고
    • Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19
    • DOI 10.1021/bi010254c
    • Ha-Duong NT, Dijols S, Macherey AC, Goldstein JA, Dansette PM, and Mansuy D (2001) Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40:12112-12122. (Pubitemid 32946552)
    • (2001) Biochemistry , vol.40 , Issue.40 , pp. 12112-12122
    • Ha-Duong, N.-T.1    Dijols, S.2    Macherey, A.-C.3    Goldstein, J.A.4    Dansette, P.M.5    Mansuy, D.6
  • 12
    • 0031041652 scopus 로고    scopus 로고
    • Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4. Role of residues 210 and 211 in flavonoid activation and substrate specificity
    • DOI 10.1074/jbc.272.9.5396
    • Harlow GR and Halpert JR (1997) Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4. Role of residues 210 and 211 in flavonoid activation and substrate specificity. J Biol Chem 272:5396-5402. (Pubitemid 27102356)
    • (1997) Journal of Biological Chemistry , vol.272 , Issue.9 , pp. 5396-5402
    • Harlow, G.R.1    Halpert, J.R.2
  • 13
    • 27544516024 scopus 로고    scopus 로고
    • Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases
    • DOI 10.1016/j.bbrc.2005.08.190, PII S0006291X05019169
    • Johnson EF and Stout CD (2005) Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases. Biochem Biophys Res Commun 338:331-336. (Pubitemid 41540575)
    • (2005) Biochemical and Biophysical Research Communications , vol.338 , Issue.1 , pp. 331-336
    • Johnson, E.F.1    Stout, C.D.2
  • 14
    • 0037243921 scopus 로고    scopus 로고
    • The thienopyridine derivatives (platelet adenosine diphosphate receptor antagonists), pharmacology and clinical developments
    • DOI 10.1046/j.1365-2044.2003.02960.x
    • Kam PC and Nethery CM (2003) The thienopyridine derivatives (platelet adenosine diphosphate receptor antagonists), pharmacology and clinical developments. Anaesthesia 58:28-35. (Pubitemid 36113325)
    • (2003) Anaesthesia , vol.58 , Issue.1 , pp. 28-35
    • Kam, P.C.A.1    Nethery, C.M.2
  • 15
    • 0036178095 scopus 로고    scopus 로고
    • Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: An evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation
    • DOI 10.1124/mol.61.3.495
    • Khan KK, He YQ, Domanski TL, and Halpert JR (2002) Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: an evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation. Mol Pharmacol 61:495-506. (Pubitemid 34171915)
    • (2002) Molecular Pharmacology , vol.61 , Issue.3 , pp. 495-506
    • Khan, K.K.1    You, Q.H.2    Domanski, T.L.3    Halpert, J.R.4
  • 16
    • 0034128040 scopus 로고    scopus 로고
    • In vitro inhibition of the cytochrome P450 (CYP450) system by the antiplatelet drug ticlopidine: Potent effect on CYP2C19 and CYP2D6
    • DOI 10.1046/j.1365-2125.2000.00175.x
    • Ko JW, Desta Z, Soukhova NV, Tracy T, and Flockhart DA (2000) In vitro inhibition of the cytochrome P450 (CYP450) system by the antiplatelet drug ticlopidine: potent effect on CYP2C19 and CYP2D6. Brit J Clin Pharmacol 49:343-351. (Pubitemid 30195277)
    • (2000) British Journal of Clinical Pharmacology , vol.49 , Issue.4 , pp. 343-351
    • Ko, J.W.1    Desta, Z.2    Soukhova, N.V.3    Tracy, T.4    Flockhart, D.A.5
  • 17
    • 21244500925 scopus 로고    scopus 로고
    • Directed evolution of mammalian cytochrome P450 2B1: Mutations outside of the active site enhance the metabolism of several substrates, including the anticancer prodrugs cyclophosphamide and ifosfamide
    • DOI 10.1074/jbc.M500158200
    • Kumar S, Chen CS, Waxman DJ, and Halpert JR (2005) Directed evolution of mammalian cytochrome P4502 B1: mutations outside of the active site enhance the metabolism of several substrates, including the anticancer prodrugs cyclophosphamide and ifosfamide. J Biol Chem 280:19569-19575. (Pubitemid 41379478)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.20 , pp. 19569-19575
    • Kumar, S.1    Chen, C.S.2    Waxman, D.J.3    Halpert, J.R.4
  • 18
    • 35548933849 scopus 로고    scopus 로고
    • 264>Phe substitution
    • DOI 10.1124/mol.107.039693
    • Kumar S, Zhao Y, Sun L, Negi SS, Halpert JR, and Muralidhara BK (2007) Rational engineering of human cytochrome P450 2B6 for enhanced expression and stability: importance of a Leu264->Phe substitution. Mol Pharmacol 72:1191-1199. (Pubitemid 350012593)
    • (2007) Molecular Pharmacology , vol.72 , Issue.5 , pp. 1191-1199
    • Kumar, S.1    Zhao, Y.2    Sun, L.3    Negi, S.S.4    Halpert, J.R.5    Muralidhara, B.K.6
  • 19
    • 52649175489 scopus 로고    scopus 로고
    • Human cytochromes P450 in the metabolism of drugs: New molecular models of enzyme-substrate interactions
    • Lewis DF and Ito Y (2008) Human cytochromes P450 in the metabolism of drugs: new molecular models of enzyme-substrate interactions. Expert Opin Drug Metab Toxicol 4:1181-1186.
    • (2008) Expert Opin Drug Metab Toxicol , vol.4 , pp. 1181-1186
    • Lewis, D.F.1    Ito, Y.2
  • 21
    • 33645384437 scopus 로고    scopus 로고
    • Improvement in the expression of CYP2B6 by co-expression with molecular chaperones GroES/EL in Escherichia coli
    • Mitsuda M and Iwasaki M (2006) Improvement in the expression of CYP2B6 by co-expression with molecular chaperones GroES/EL in Escherichia coli. Protein Expr Purif 46:401-405.
    • (2006) Protein Expr Purif , vol.46 , pp. 401-405
    • Mitsuda, M.1    Iwasaki, M.2
  • 22
    • 61449129603 scopus 로고    scopus 로고
    • Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrel
    • Nishiya Y, Hagihara K, Ito T, Tajima M, Miura S, Kurihara A, Farid NA, and Ikeda T (2009) Mechanism-based inhibition of human cytochrome P450 2B6 by ticlopidine, clopidogrel, and the thiolactone metabolite of prasugrel. Drug Metab Dispos 37:589-593.
    • (2009) Drug Metab Dispos , vol.37 , pp. 589-593
    • Nishiya, Y.1    Hagihara, K.2    Ito, T.3    Tajima, M.4    Miura, S.5    Kurihara, A.6    Farid, N.A.7    Ikeda, T.8
  • 23
    • 0030660230 scopus 로고    scopus 로고
    • Engineering the substrate specificity of Bacillus megaterium cytochrome P-450 BM3: Hydroxylation of alkyl trimethylammonium compounds
    • Oliver CF, Modi S, Primrose WU, Lian LY, and Roberts GC (1997) Engineering the substrate specificity of Bacillus megaterium cytochrome P-450 BM3: hydroxylation of alkyl trimethylammonium compounds. Biochem J 327:537-544. (Pubitemid 27477834)
    • (1997) Biochemical Journal , vol.327 , Issue.2 , pp. 537-544
    • Oliver, C.F.1    Modi, S.2    Primrose, W.U.3    Lian, L.-Y.4    Roberts, G.C.K.5
  • 24
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature
    • Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
    • (1964) J Biol Chem , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 27
    • 0021024134 scopus 로고
    • Ticlopidine: A promise for the prevention and treatment of thrombosis and its complications
    • Panak E, Maffrand JP, Picard-Fraire C, Vallee E, Blanchard J, and Roncucci R (1983) Ticlopidine: a promise for the prevention and treatment of thrombosis and its complications. Haemostasis 13 (Suppl 1):1-54.
    • (1983) Haemostasis , vol.13 , Issue.SUPPL. 1 , pp. 1-54
    • Panak, E.1    Maffrand, J.P.2    Picard-Fraire, C.3    Vallee, E.4    Blanchard, J.5    Roncucci, R.6
  • 29
    • 0035500087 scopus 로고    scopus 로고
    • A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function
    • DOI 10.1006/abbi.2001.2574
    • Scott EE, Spatzenegger M, and Halpert JR (2001) A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function. Arch Biochem Biophys 395:57-68. (Pubitemid 33030143)
    • (2001) Archives of Biochemistry and Biophysics , vol.395 , Issue.1 , pp. 57-68
    • Scott, E.E.1    Spatzenegger, M.2    Halpert, J.R.3
  • 30
    • 3042553224 scopus 로고    scopus 로고
    • Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl)imidazole at 1.9-A resolution: Insight into the range of P450 conformations and the coordination of redox partner binding
    • DOI 10.1074/jbc.M403349200
    • Scott EE, White MA, He YA, Johnson EF, Stout CD, and Halpert JR (2004) Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl) imidazole at 1.9-A resolution: insight into the range of P450 conformations and the coordination of redox partner binding. J Biol Chem 279:27294-27301. (Pubitemid 38812569)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.26 , pp. 27294-27301
    • Scott, E.E.1    White, M.A.2    He, Y.A.3    Johnson, E.F.4    Stout, C.D.5    Halpert, J.R.6
  • 31
    • 0032168873 scopus 로고    scopus 로고
    • The antiplatelet effects of ticlopidine and clopidogrel
    • Sharis PJ, Cannon CP, and Loscalzo J (1998) The antiplatelet effects of ticlopidine and clopidogrel. Ann Intern Med 129:394-405. (Pubitemid 28402795)
    • (1998) Annals of Internal Medicine , vol.129 , Issue.5 , pp. 394-405
    • Sharis, P.J.1    Cannon, C.P.2    Loscalzo, J.3
  • 32
    • 70349117785 scopus 로고    scopus 로고
    • Metabolism of ticlopidine in rats: Identification of the main biliary metabolite as a glutathione conjugate of ticlopidine S-oxide
    • Shimizu S, Atsumi R, Nakazawa T, Fujimaki Y, Sudo K, and Okazaki O (2009) Metabolism of ticlopidine in rats: identification of the main biliary metabolite as a glutathione conjugate of ticlopidine S-oxide. Drug Metab Dispos 37:1904-1915.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1904-1915
    • Shimizu, S.1    Atsumi, R.2    Nakazawa, T.3    Fujimaki, Y.4    Sudo, K.5    Okazaki, O.6
  • 33
    • 0033518847 scopus 로고    scopus 로고
    • Incidence and clinical course of thrombotic thrombocytopenic purpura due to ticlopidine following coronary stenting
    • DOI 10.1001/jama.281.9.806
    • Steinhubl SR, Tan WA, Foody JM, and Topol EJ (1999) Incidence and clinical course of thrombotic thrombocytopenic purpura due to ticlopidine following coronary stenting. EPISTENT Investigators. Evaluation of platelet IIb/IIIa inhibitor for stenting. JAMA 281:806-810. (Pubitemid 29113740)
    • (1999) Journal of the American Medical Association , vol.281 , Issue.9 , pp. 806-810
    • Steinhubl, S.R.1    Tan, W.A.2    Foody, J.M.3    Topol, E.J.4
  • 34
    • 0142103879 scopus 로고    scopus 로고
    • Crystallographic Studies on the Complex Behavior of Nicotine Binding to P450cam (CYP101)
    • DOI 10.1021/bi034833o
    • Strickler M, Goldstein BM, Maxfield K, Shireman L, Kim G, Matteson DS, and Jones JP (2003) Crystallographic studies on the complex behavior of nicotine binding to P450cam (CYP101). Biochemistry 42:11943-11950. (Pubitemid 37280644)
    • (2003) Biochemistry , vol.42 , Issue.41 , pp. 11943-11950
    • Strickler, M.1    Goldstein, B.M.2    Maxfield, K.3    Shireman, L.4    Kim, G.5    Matteson, D.S.6    Jones, J.P.7
  • 35
    • 75549091169 scopus 로고    scopus 로고
    • Rational engineering of cytochromes P450 2B6 and 2B11 for enhanced stability: Insights into structural importance of residue 334
    • Talakad JC, Wilderman PR, Davydov DR, Kumar S, and Halpert JR (2010) Rational engineering of cytochromes P450 2B6 and 2B11 for enhanced stability: insights into structural importance of residue 334. Arch Biochem Biophys 494:151-158.
    • (2010) Arch Biochem Biophys , vol.494 , pp. 151-158
    • Talakad, J.C.1    Wilderman, P.R.2    Davydov, D.R.3    Kumar, S.4    Halpert, J.R.5
  • 36
    • 0019488915 scopus 로고
    • Metabolism of ticlopidine in rats: Identification and quantitative determination of some of its metabolites in plasma, urine and bile
    • Tuong A, Bouyssou A, Paret J, and Cuong TG (1981) Metabolism of ticlopidine in rats: Identification and quantitative determination of some its metabolites in plasma, urine and bile. Eur J Drug Metab Pharmacokinet 6:91-98. (Pubitemid 11032654)
    • (1981) European Journal of Drug Metabolism and Pharmacokinetics , vol.6 , Issue.2 , pp. 91-98
    • Tuong, A.1    Bouyssou, A.2    Paret, J.3    Tuong, T.G.4
  • 37
    • 33750711672 scopus 로고    scopus 로고
    • Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6
    • DOI 10.1177/0091270006293753
    • Walsky RL, Astuccio AV, and Obach RS (2006) Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol 46:1426-1438. (Pubitemid 44704203)
    • (2006) Journal of Clinical Pharmacology , vol.46 , Issue.12 , pp. 1426-1438
    • Walsky, R.L.1    Astuccio, A.V.2    Obach, R.S.3
  • 38
    • 70350457938 scopus 로고    scopus 로고
    • Tert-Butylphenylacetylene is a potent mechanism-based inactivator of cytochrome P450 2B4: Inhibition of cytochrome P450 catalysis by steric hindrance
    • Zhang H, Lin HL, Walker VJ, Hamdane D, and Hollenberg PF (2009) tert-Butylphenylacetylene is a potent mechanism-based inactivator of cytochrome P450 2B4: inhibition of cytochrome P450 catalysis by steric hindrance. Mol Pharmacol 76:1011-1018.
    • (2009) Mol Pharmacol , vol.76 , pp. 1011-1018
    • Zhang, H.1    Lin, H.L.2    Walker, V.J.3    Hamdane, D.4    Hollenberg, P.F.5
  • 39
    • 34548423359 scopus 로고    scopus 로고
    • Structural and thermodynamic consequences of 1-(4-chlorophenyl)imidazole binding to cytochrome P450 2B4
    • DOI 10.1021/bi7011614
    • Zhao Y, Sun L, Muralidhara BK, Kumar S, White MA, Stout CD, and Halpert JR (2007) Structural and thermodynamic consequences of 1-(4-chlorophenyl) imidazole binding to cytochrome P450 2B4. Biochemistry 46:11559-11567. (Pubitemid 47585501)
    • (2007) Biochemistry , vol.46 , Issue.41 , pp. 11559-11567
    • Zhao, Y.1    Sun, L.2    Muralidhara, B.K.3    Kumar, S.4    White, M.A.5    Stout, C.D.6    Halpert, J.R.7
  • 40
    • 33646854265 scopus 로고    scopus 로고
    • Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: Insight into P450 conformational plasticity and membrane interaction
    • DOI 10.1074/jbc.M511464200
    • Zhao Y, White MA, Muralidhara BK, Sun L, Halpert JR, and Stout CD (2006) Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: insight into P450 conformational plasticity and membrane interaction. J Biol Chem 281:5973-5981. (Pubitemid 43847698)
    • (2006) Journal of Biological Chemistry , vol.281 , Issue.9 , pp. 5973-5981
    • Zhao, Y.1    White, M.A.2    Muralidhara, B.K.3    Sun, L.4    Halpert, J.R.5    Stout, C.D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.