메뉴 건너뛰기




Volumn 42, Issue 1, 2014, Pages 141-152

Multiple cytochrome P450 isoforms are involved in the generation of a pharmacologically active thiol metabolite, whereas paraoxonase 1 and carboxylesterase 1 catalyze the formation of a thiol metabolite isomer from ticlopidine

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOTICLOPIDINE; ARYLDIALKYLPHOSPHATASE 1; BIS(4 NITROPHENYL) PHOSPHATE; CALCIUM CHLORIDE; CARBOXYLESTERASE; CARBOXYLESTERASE 1; CLOPIDOGREL; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; DIISOPROPYLPHOSPHOROFLUORIDE; DRUG METABOLITE; EDETIC ACID; ENZYME INHIBITOR; ESTERASE INHIBITOR; ISOENZYME; PIPERIDINE; RECOMBINANT ENZYME; THIOL; TICLOPIDINE; UNCLASSIFIED DRUG;

EID: 84890625289     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.053017     Document Type: Article
Times cited : (14)

References (45)
  • 1
    • 80054785029 scopus 로고    scopus 로고
    • Dissecting the activation of thienopyridines by cytochromes P450 using a pharmacodynamic assay in vitro
    • Abell LM and Liu EC (2011) Dissecting the activation of thienopyridines by cytochromes P450 using a pharmacodynamic assay in vitro. J Pharmacol Exp Ther 339:589-596.
    • (2011) J Pharmacol Exp Ther , vol.339 , pp. 589-596
    • Abell, L.M.1    Liu, E.C.2
  • 2
    • 34147182339 scopus 로고    scopus 로고
    • Ticlopidine could be an alternative therapy in the case of pharmacological resistance to clopidogrel: A report of three cases [10]
    • DOI 10.1111/j.1538-7836.2007.02338.x
    • Aleil B, Rochoux G, Monassier JP, Cazenave JP, and Gachet C (2007) Ticlopidine could be an alternative therapy in the case of pharmacological resistance to clopidogrel: a report of three cases. J Thromb Haemost 5:879-881. (Pubitemid 46563597)
    • (2007) Journal of Thrombosis and Haemostasis , vol.5 , Issue.4 , pp. 879-881
    • Aleil, B.1    Rochoux, G.2    Monassier, J.-P.3    Cazenave, J.-P.4    Gachet, C.5
  • 5
    • 84861524089 scopus 로고    scopus 로고
    • Metabolism and neurotoxicity of homo-cysteine thiolactone in mice: Evidence for a protective role of paraoxonase 1
    • Borowczyk K, Shih DM, and Jakubowski H (2012) Metabolism and neurotoxicity of homo-cysteine thiolactone in mice: evidence for a protective role of paraoxonase 1. J Alzheimers Dis 30:225-231.
    • (2012) J Alzheimers Dis , vol.30 , pp. 225-231
    • Borowczyk, K.1    Shih, D.M.2    Jakubowski, H.3
  • 7
    • 84862249165 scopus 로고    scopus 로고
    • Recent advances in the pharmacogenetics of clopidogrel
    • Cuisset T, Morange PE, and Alessi MC (2012) Recent advances in the pharmacogenetics of clopidogrel. Hum Genet 131:653-664.
    • (2012) Hum Genet , vol.131 , pp. 653-664
    • Cuisset, T.1    Morange, P.E.2    Alessi, M.C.3
  • 8
    • 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 (2012a) 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
  • 9
    • 84861325361 scopus 로고    scopus 로고
    • Metabolic activation of prasugrel: Nature of the two competitive pathways resulting in the opening of its thiophene ring
    • Dansette PM, Rosi J, Debernardi J, Bertho G, and Mansuy D (2012b) Metabolic activation of prasugrel: nature of the two competitive pathways resulting in the opening of its thiophene ring. Chem Res Toxicol 25:1058-1065.
    • (2012) Chem Res Toxicol , vol.25 , pp. 1058-1065
    • Dansette, P.M.1    Rosi, J.2    Debernardi, J.3    Bertho, G.4    Mansuy, D.5
  • 10
    • 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
  • 12
    • 78649611141 scopus 로고    scopus 로고
    • In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human car-boxylesterase activities
    • Fukami T, Takahashi S, Nakagawa N, Maruichi T, Nakajima M, and Yokoi T (2010) In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human car-boxylesterase activities. Drug Metab Dispos 38:2173-2178.
    • (2010) Drug Metab Dispos , vol.38 , pp. 2173-2178
    • Fukami, T.1    Takahashi, S.2    Nakagawa, N.3    Maruichi, T.4    Nakajima, M.5    Yokoi, T.6
  • 13
    • 0031214358 scopus 로고    scopus 로고
    • Inhibition of paraoxonase activity in human liver microsomes by exposure to EDTA, metals and mercurials
    • DOI 10.1016/S0009-2797(97)00046-X, PII S000927979700046X
    • Gonzalvo MC, Gil F, Hernández AF, Villanueva E, and Pla A (1997) Inhibition of paraoxonase activity in human liver microsomes by exposure to EDTA, metals and mercurials. Chem Biol Interact 105:169-179. (Pubitemid 27353307)
    • (1997) Chemico-Biological Interactions , vol.105 , Issue.3 , pp. 169-179
    • Gonzalvo, M.C.1    Gil, F.2    Hernandez, A.F.3    Villanueva, E.4    Pla, A.5
  • 15
    • 0038649988 scopus 로고    scopus 로고
    • Clopidogrel for coronary stenting: Response variability, drug resistance, and the effect of pretreatment platelet reactivity
    • DOI 10.1161/01.CIR.0000072771.11429.83
    • Gurbel PA, Bliden KP, Hiatt BL, and O'Connor CM (2003) Clopidogrel for coronary stenting: response variability, drug resistance, and the effect of pretreatment platelet reactivity. Circulation 107:2908-2913. (Pubitemid 36736631)
    • (2003) Circulation , vol.107 , Issue.23 , pp. 2908-2913
    • Gurbel, P.A.1    Bliden, K.P.2    Hiatt, B.L.3    O'Connor, C.M.4
  • 16
    • 70350332201 scopus 로고    scopus 로고
    • A possible mechanism for the differences in efficiency and variability of active metabolite formation from thienopyridine antiplatelet agents, prasugrel and clopidogrel
    • Hagihara K, Kazui M, Kurihara A, Yoshiike M, Honda K, Okazaki O, Farid NA, and Ikeda T (2009) A possible mechanism for the differences in efficiency and variability of active metabolite formation from thienopyridine antiplatelet agents, prasugrel and clopidogrel. Drug Metab Dispos 37:2145-2152.
    • (2009) Drug Metab Dispos , vol.37 , pp. 2145-2152
    • Hagihara, K.1    Kazui, M.2    Kurihara, A.3    Yoshiike, M.4    Honda, K.5    Okazaki, O.6    Farid, N.A.7    Ikeda, T.8
  • 17
    • 0014097486 scopus 로고
    • Phosphoric acid-bis-(p-nitro-phenylester), a new inhibitor of microsomal carboxylesterases [article in German]
    • Heymann E and Krisch K (1967) Phosphoric acid-bis-(p-nitro-phenylester), a new inhibitor of microsomal carboxylesterases [article in German]. Hoppe Seylers Z Physiol Chem 348: 609-619.
    • (1967) Hoppe Seylers Z Physiol Chem , vol.348 , pp. 609-619
    • Heymann, E.1    Krisch, K.2
  • 18
    • 79960578142 scopus 로고    scopus 로고
    • Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis
    • Hioki T, Fukami T, Nakajima M, and Yokoi T (2011) Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis. Drug Metab Dispos 39:1345-1352.
    • (2011) Drug Metab Dispos , vol.39 , pp. 1345-1352
    • Hioki, T.1    Fukami, T.2    Nakajima, M.3    Yokoi, T.4
  • 19
    • 82955240702 scopus 로고    scopus 로고
    • CYP2C19 but not PON1 genetic variants influence clopidogrel pharmacokinetics, pharmacodynamics, and clinical efficacy in post-myocardial infarction patients
    • Hulot JS, Collet JP, Cayla G, Silvain J, Allanic F, Bellemain-Appaix A, Scott SA, and Montalescot G (2011) CYP2C19 but not PON1 genetic variants influence clopidogrel pharmacokinetics, pharmacodynamics, and clinical efficacy in post-myocardial infarction patients. Circ Cardiovasc Interv 4:422-428.
    • (2011) Circ Cardiovasc Interv , vol.4 , pp. 422-428
    • Hulot, J.S.1    Collet, J.P.2    Cayla, G.3    Silvain, J.4    Allanic, F.5    Bellemain-Appaix, A.6    Scott, S.A.7    Montalescot, G.8
  • 21
    • 0035087714 scopus 로고    scopus 로고
    • Cholinesterase-like catalytic antibodies: Reaction with substrates and inhibitors
    • DOI 10.1016/S0161-5890(00)00104-8, PII S0161589000001048
    • Johnson G and Moore SW (2000) Cholinesterase-like catalytic antibodies: reaction with substrates and inhibitors. Mol Immunol 37:707-719. (Pubitemid 32244119)
    • (2001) Molecular Immunology , vol.37 , Issue.12-13 , pp. 707-719
    • Johnson, G.1    Moore, S.W.2
  • 22
    • 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
  • 24
    • 0031814242 scopus 로고    scopus 로고
    • Adverse haematological effects of ticlopidine
    • Love BB, Biller J, and Gent M (1998) Adverse haematological effects of ticlopidine. Prevention, recognition and management. Drug Saf 19:89-98. (Pubitemid 28389035)
    • (1998) Drug Safety , vol.19 , Issue.2 , pp. 89-98
    • Love, B.B.1    Biller, J.2    Gent, M.3
  • 25
    • 0031859456 scopus 로고    scopus 로고
    • Serum paraoxonase (PON1) 55 and 192 polymorphism and paraoxonase activity and concentration in non-insulin dependent diabetes mellitus
    • DOI 10.1016/S0021-9150(98)00095-1, PII S0021915098000951
    • Mackness B, Mackness MI, Arrol S, Turkie W, Julier K, Abuasha B, Miller JE, Boulton AJ, and Durrington PN (1998) Serum paraoxonase (PON1) 55 and 192 polymorphism and para-oxonase activity and concentration in non-insulin dependent diabetes mellitus. Atherosclerosis 139:341-349. (Pubitemid 28361819)
    • (1998) Atherosclerosis , vol.139 , Issue.2 , pp. 341-349
    • MacKness, B.1    MacKness, M.I.2    Arrol, S.3    Turkie, W.4    Julier, K.5    Abuasha, B.6    Miller, J.E.7    Boulton, A.J.M.8    Durrington, P.N.9
  • 28
    • 70350325443 scopus 로고    scopus 로고
    • Comparison of mechanism-based inhibition of human cytochrome P450 2C19 by ticlopidine, clopidogrel, and prasugrel
    • Nishiya Y, Hagihara K, Kurihara A, Okudaira N, Farid NA, Okazaki O, and Ikeda T (2009a) Comparison of mechanism-based inhibition of human cytochrome P450 2C19 by ticlopidine, clopidogrel, and prasugrel. Xenobiotica 39:836-843.
    • (2009) Xenobiotica , vol.39 , pp. 836-843
    • Nishiya, Y.1    Hagihara, K.2    Kurihara, A.3    Okudaira, N.4    Farid, N.A.5    Okazaki, O.6    Ikeda, T.7
  • 29
    • 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 (2009b) 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
  • 30
    • 0029873941 scopus 로고    scopus 로고
    • Ticlopidine, A review of its pharmacology, clinical efficacy and tolerability in the prevention of cerebral ischaemia and stroke
    • Noble S and Goa KL (1996) Ticlopidine. A review of its pharmacology, clinical efficacy and tolerability in the prevention of cerebral ischaemia and stroke. Drugs Aging 8:214-232.
    • (1996) Drugs Aging , vol.8 , pp. 214-232
    • Noble, S.1    Goa, K.L.2
  • 32
    • 0029950130 scopus 로고    scopus 로고
    • Arylacetamide deacetylase activity towards mono-acetyldapsone. Species comparison, factors that influence activity, and comparison with 2-acetylaminofluorene and p-nitrophenyl acetate hydrolysis
    • Preuss CV and Svensson CK (1996) Arylacetamide deacetylase activity towards mono-acetyldapsone. Species comparison, factors that influence activity, and comparison with 2-acetylaminofluorene and p-nitrophenyl acetate hydrolysis. Biochem Pharmacol 51:1661-1668.
    • (1996) Biochem Pharmacol , vol.51 , pp. 1661-1668
    • Preuss, C.V.1    Svensson, C.K.2
  • 35
    • 84859899711 scopus 로고    scopus 로고
    • Conclusive identification of the oxybutynin-hydrolyzing enzyme in human liver
    • Sato Y, Miyashita A, Iwatsubo T, and Usui T (2012) Conclusive identification of the oxybutynin-hydrolyzing enzyme in human liver. Drug Metab Dispos 40:902-906.
    • (2012) Drug Metab Dispos , vol.40 , pp. 902-906
    • Sato, Y.1    Miyashita, A.2    Iwatsubo, T.3    Usui, T.4
  • 36
    • 84863049281 scopus 로고    scopus 로고
    • Ilaprazole, a new proton pump inhibitor, is primarily metabolized to ilaprazole sulfone by CYP3A4 and 3A5
    • Seo KA, Lee SJ, Kim KB, Bae SK, Liu KH, Kim DH, and Shin JG (2012) Ilaprazole, a new proton pump inhibitor, is primarily metabolized to ilaprazole sulfone by CYP3A4 and 3A5. Xenobiotica 42:278-284.
    • (2012) Xenobiotica , vol.42 , pp. 278-284
    • Seo, K.A.1    Lee, S.J.2    Kim, K.B.3    Bae, S.K.4    Liu, K.H.5    Kim, D.H.6    Shin, J.G.7
  • 37
    • 33751173450 scopus 로고    scopus 로고
    • Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel
    • Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, and Yan B (2006) Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 319: 1477-1484.
    • (2006) J Pharmacol Exp Ther , vol.319 , pp. 1477-1484
    • Shi, D.1    Yang, J.2    Yang, D.3    Lecluyse, E.L.4    Black, C.5    You, L.6    Akhlaghi, F.7    Yan, B.8
  • 39
    • 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. EPIS-TENT 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
  • 41
    • 79951873368 scopus 로고    scopus 로고
    • Comparison of in vitro metabolism of ticlopidine by human cytochrome P450 2B6 and rabbit cytochrome P450 2B4
    • Talakad JC, Shah MB, Walker GS, Xiang C, Halpert JR, and Dalvie D (2011) Comparison of in vitro metabolism of ticlopidine by human cytochrome P450 2B6 and rabbit cytochrome P450 2B4. Drug Metab Dispos 39:539-550.
    • (2011) Drug Metab Dispos , vol.39 , pp. 539-550
    • Talakad, J.C.1    Shah, M.B.2    Walker, G.S.3    Xiang, C.4    Halpert, J.R.5    Dalvie, D.6
  • 42
    • 0031920093 scopus 로고    scopus 로고
    • Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent
    • Tougou K, Nakamura A, Watanabe S, Okuyama Y, and Morino A (1998) Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent. Drug Metab Dispos 26:355-359. (Pubitemid 28201246)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.4 , pp. 355-359
    • Tougou, K.1    Nakamura, A.2    Watanabe, S.3    Okuyama, Y.4    Morino, A.5
  • 44
    • 0021996062 scopus 로고
    • Clinical significance of esterases in man
    • Williams FM (1985) Clinical significance of esterases in man. Clin Pharmacokinet 10:392-403. (Pubitemid 15242339)
    • (1985) Clinical Pharmacokinetics , vol.10 , Issue.5 , pp. 392-403
    • Williams, F.M.1
  • 45
    • 80053954075 scopus 로고    scopus 로고
    • Pharmacogenomics of clopidogrel: Evidence and perspectives
    • Yin T and Miyata T (2011) Pharmacogenomics of clopidogrel: evidence and perspectives. Thromb Res 128:307-316.
    • (2011) Thromb Res , vol.128 , pp. 307-316
    • Yin, T.1    Miyata, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.