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Volumn 39, Issue 7, 2011, Pages 1247-1254

Combination of GSH trapping and time-dependent inhibition assays as a predictive method of drugs generating highly reactive metabolites

Author keywords

[No Author keywords available]

Indexed keywords

AMODIAQUINE; ATORVASTATIN; BENZBROMARONE; CARBAMAZEPINE; CELECOXIB; CLOPIDOGREL; CLOZAPINE; DONEPEZIL; DRUG METABOLITE; FLUTAMIDE; FUROSEMIDE; IMIPRAMINE; LEVOFLOXACIN; NEVIRAPINE; OLANZAPINE; OLMESARTAN; PIOGLITAZONE; PRAVASTATIN; PROPRANOLOL; ROSIGLITAZONE; SULFAMETHOXAZOLE; TACRINE; TAMOXIFEN; TICLOPIDINE; TIENILIC ACID; UNINDEXED DRUG; VALSARTAN; WARFARIN; ZAFIRLUKAST; ZOMEPIRAC;

EID: 79959400794     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.039180     Document Type: Article
Times cited : (26)

References (56)
  • 1
    • 33748656068 scopus 로고    scopus 로고
    • Thiazolidinedione bioactivation: A comparison of the bioactivation potentials of troglitazone, rosiglitazone, and pioglitazone using stable isotope-labeled analogues and liquid chromatography tandem mass spectrometry
    • DOI 10.1021/tx050353h
    • Alvarez-Sanchez R, Montavon F, Hartung T, and Pähler A (2006) Thiazolidinedione bioactivation: a comparison of the bioactivation potentials of troglitazone, rosiglitazone, and pioglitazone using stable isotope-labeled analogues and liquid chromatography tandem mass spectrometry. Chem Res Toxicol 19:1106-1116. (Pubitemid 44384842)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.8 , pp. 1106-1116
    • Alvarez-Sanchez, R.1    Montavon, F.2    Hartung, T.3    Pahler, A.4
  • 2
    • 0026724498 scopus 로고
    • Metabolism of valproate to hepatotoxic intermediates
    • Baillie TA (1992) Metabolism of valproate to hepatotoxic intermediates. Pharm Weekbl Sci 14:122-125.
    • (1992) Pharm Weekbl Sci , vol.14 , pp. 122-125
    • Baillie, T.A.1
  • 3
    • 33746255370 scopus 로고    scopus 로고
    • Future of toxicology-metabolic activation and drug design: Challenges and opportunities in chemical toxicology
    • Baillie TA (2006) Future of toxicology-metabolic activation and drug design: challenges and opportunities in chemical toxicology. Chem Res Toxicol 19:889-893.
    • (2006) Chem Res Toxicol , vol.19 , pp. 889-893
    • Baillie, T.A.1
  • 4
    • 62249155473 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from non-hepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction
    • Bauman JN, Kelly JM, Tripathy S, Zhao SX, Lam WW, Kalgutkar AS, and Obach RS (2009) Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from non-hepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction. Chem Res Toxicol 22:332-340.
    • (2009) Chem Res Toxicol , vol.22 , pp. 332-340
    • Bauman, J.N.1    Kelly, J.M.2    Tripathy, S.3    Zhao, S.X.4    Lam, W.W.5    Kalgutkar, A.S.6    Obach, R.S.7
  • 5
    • 67650783190 scopus 로고    scopus 로고
    • Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro
    • Chang SY, Chen C, Yang Z, and Rodrigues AD (2009) Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro. Drug Metab Dispos 37:1667-1675.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1667-1675
    • Chang, S.Y.1    Chen, C.2    Yang, Z.3    Rodrigues, A.D.4
  • 6
    • 0024044003 scopus 로고
    • The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: A stopped-flow kinetic study
    • Coles B, Wilson I, Wardman P, Hinson JA, Nelson SD, and Ketterer B (1988) The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: a stopped-flow kinetic study. Arch Biochem Biophys 264:253-260.
    • (1988) Arch Biochem Biophys , vol.264 , pp. 253-260
    • Coles, B.1    Wilson, I.2    Wardman, P.3    Hinson, J.A.4    Nelson, S.D.5    Ketterer, B.6
  • 7
    • 0025947068 scopus 로고
    • Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity
    • Cribb AE, Miller M, Leeder JS, Hill J, and Spielberg SP (1991) Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity. Drug Metab Dispos 19:900-906.
    • (1991) Drug Metab Dispos , vol.19 , pp. 900-906
    • Cribb, A.E.1    Miller, M.2    Leeder, J.S.3    Hill, J.4    Spielberg, S.P.5
  • 8
    • 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
  • 9
    • 1642281756 scopus 로고    scopus 로고
    • Drug-Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development
    • DOI 10.1021/tx034170b
    • Evans DC, Watt AP, Nicoll-Griffith DA, and Baillie TA (2004) Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem Res Toxicol 17:3-16. (Pubitemid 38134055)
    • (2004) Chemical Research in Toxicology , vol.17 , Issue.1 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 10
    • 67649389519 scopus 로고    scopus 로고
    • The conduct of in vitro studies to address time-dependent inhibition of drug-metabolizing enzymes: A perspective of the Pharmaceutical Research and Manufacturers of America
    • Grimm SW, Einolf HJ, Hall SD, He K, Lim HK, Ling KH, Lu C, Nomeir AA, Seibert E, Skordos KW, et al. (2009) The conduct of in vitro studies to address time-dependent inhibition of drug-metabolizing enzymes: a perspective of the Pharmaceutical Research and Manufacturers of America. Drug Metab Dispos 37:1355-1370.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1355-1370
    • Grimm, S.W.1    Einolf, H.J.2    Hall, S.D.3    He, K.4    Lim, H.K.5    Ling, K.H.6    Lu, C.7    Nomeir, A.A.8    Seibert, E.9    Skordos, K.W.10
  • 11
    • 38949099990 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human cytochromes P450s: Experimental characterization, reactive intermediates, and clinical implications
    • DOI 10.1021/tx7002504
    • Hollenberg PF, Kent UM, and Bumpus NN (2008) Mechanism-based inactivation of human cytochromes p450s: experimental characterization, reactive intermediates, and clinical implications. Chem Res Toxicol 21:189-205. (Pubitemid 351219719)
    • (2008) Chemical Research in Toxicology , vol.21 , Issue.1 , pp. 189-205
    • Hollenberg, P.F.1    Kent, U.M.2    Bumpus, N.N.3
  • 13
    • 0029910243 scopus 로고    scopus 로고
    • Oxidation of tienilic acid by human yeast-expressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9
    • Jean P, Lopez-Garcia P, Dansette P, Mansuy D, and Goldstein JL (1996) Oxidation of tienilic acid by human yeast-expressed cytochromes P-450 2C8, 2C9, 2C18 and 2C19. Evidence that this drug is a mechanism-based inhibitor specific for cytochrome P-450 2C9. Eur J Biochem 241:797-804. (Pubitemid 26379382)
    • (1996) European Journal of Biochemistry , vol.241 , Issue.3 , pp. 797-804
    • Jean, P.1    Lopez-Garcia, P.2    Dansette, P.3    Mansuy, D.4    Goldstein, J.L.5
  • 14
    • 0031844523 scopus 로고    scopus 로고
    • Oxidation of a metabolite of indomethacin (desmethyldeschlorobenzoylindomethacin) to reactive intermediates by activated neutrophils, hypochlorous acid, and the myeloperoxidase system
    • Ju C and Uetrecht JP (1998) Oxidation of a metabolite of indomethacin (Desmethyldeschlorobenzoylindomethacin) to reactive intermediates by activated neutrophils, hypochlorous acid, and the myeloperoxidase system. Drug Metab Dispos 26:676-680. (Pubitemid 28345851)
    • (1998) Drug Metabolism and Disposition , vol.26 , Issue.7 , pp. 676-680
    • Ju, C.1    Uetrecht, J.P.2
  • 15
    • 34548805504 scopus 로고    scopus 로고
    • Mechanism-based inactivation of cytochrome P450 enzymes: Chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactions
    • DOI 10.2174/138920007780866807
    • Kalgutkar AS, Obach RS, and Maurer TS (2007) Mechanism-based inactivation of cytochrome P450 enzymes: chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactions. Curr Drug Metab 8:407-447. (Pubitemid 47603408)
    • (2007) Current Drug Metabolism , vol.8 , Issue.5 , pp. 407-447
    • Kalgutkar, A.S.1    Obach, R.S.2    Maurer, T.S.3
  • 16
    • 34250698951 scopus 로고    scopus 로고
    • Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes
    • DOI 10.1124/dmd.107.014860
    • Kang P, Dalvie D, Smith E, Zhou S, and Deese A (2007) Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos 35:1081-1088. (Pubitemid 46956427)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.7 , pp. 1081-1088
    • Kang, P.1    Dalvie, D.2    Smith, E.3    Zhou, S.4    Deese, A.5
  • 17
    • 20844444779 scopus 로고    scopus 로고
    • Idiosyncratic drug hepatotoxicity
    • Kaplowitz N (2005) Idiosyncratic drug hepatotoxicity. Nat Rev Drug Discov 4:489-499.
    • (2005) Nat Rev Drug Discov , vol.4 , pp. 489-499
    • Kaplowitz, N.1
  • 18
    • 25444434659 scopus 로고    scopus 로고
    • Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme
    • DOI 10.1021/tx050092b
    • Kassahun K, Skordos K, McIntosh I, Slaughter D, Doss GA, Baillie TA, and Yost GS (2005) Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha,beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme. Chem Res Toxicol 18:1427-1437. (Pubitemid 41361716)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.9 , pp. 1427-1437
    • Kassahun, K.1    Skordos, K.2    McIntosh, I.3    Slaughter, D.4    Doss, G.A.5    Baillie, T.A.6    Yost, G.S.7
  • 19
    • 33644536707 scopus 로고    scopus 로고
    • Identification of 17-alpha-ethynylestradiol-modified active site peptides and glutathione conjugates formed during metabolism and inactivation of P450s 2B1 and 2B6
    • Kent UM, Lin HL, Mills DE, Regal KA, and Hollenberg PF (2006) Identification of 17-alpha-ethynylestradiol-modified active site peptides and glutathione conjugates formed during metabolism and inactivation of P450s 2B1 and 2B6. Chem Res Toxicol 19:279-287.
    • (2006) Chem Res Toxicol , vol.19 , pp. 279-287
    • Kent, U.M.1    Lin, H.L.2    Mills, D.E.3    Regal, K.A.4    Hollenberg, P.F.5
  • 20
    • 0033912433 scopus 로고    scopus 로고
    • Disposition of valproic acid in maternal, fetal, and newborn sheep II: Metabolism and renal elimination
    • Kumar S, Wong H, Yeung SA, Riggs KW, Abbott FS, and Rurak DW (2000) Disposition of valproic acid in maternal, fetal, and newborn sheep. II: metabolism and renal elimination. Drug Metab Dispos 28:857-864. (Pubitemid 30470836)
    • (2000) Drug Metabolism and Disposition , vol.28 , Issue.7 , pp. 857-864
    • Kumar, S.1    Wong, H.2    Yeung, S.A.3    Riggs, K.W.4    Abbott, F.S.5    Rurak, D.W.6
  • 21
    • 37849042912 scopus 로고    scopus 로고
    • Minimizing metabolic activation during pharmaceutical lead optimization: Progress, knowledge gaps and future directions
    • Kumar S, Kassahun K, Tschirret-Guth RA, Mitra K, and Baillie TA (2008) Minimizing metabolic activation during pharmaceutical lead optimization: progress, knowledge gaps and future directions. Curr Opin Drug Discov Dev 11:43-52.
    • (2008) Curr Opin Drug Discov Dev , vol.11 , pp. 43-52
    • Kumar, S.1    Kassahun, K.2    Tschirret-Guth, R.A.3    Mitra, K.4    Baillie, T.A.5
  • 22
    • 77949314422 scopus 로고    scopus 로고
    • Approaches for minimizing metabolic activation of new drug candidates in drug discovery
    • Kumar S, Mitra K, Kassahun K, and Baillie TA (2009) Approaches for minimizing metabolic activation of new drug candidates in drug discovery. Handb Exp Pharmacol 511-544.
    • (2009) Handb Exp Pharmacol , pp. 511-544
    • Kumar, S.1    Mitra, K.2    Kassahun, K.3    Baillie, T.A.4
  • 23
    • 0020632391 scopus 로고
    • Formation of inactive cytochrome P-450 Fe(II)-metabolite complexes with several erythromycin derivatives but not with josamycin and midecamycin in rats
    • DOI 10.1016/0006-2952(83)90470-7
    • Larrey D, Tinel M, and Pessayre D (1983) Formation of inactive cytochrome P-450 Fe(II)- metabolite complexes with several erythromycin derivatives but not with josamycin and midecamycin in rats. Biochem Pharmacol 32:1487-1493. (Pubitemid 13096006)
    • (1983) Biochemical Pharmacology , vol.32 , Issue.9 , pp. 1487-1493
    • Larrey, D.1    Tinel, M.2    Pessayre, D.3
  • 24
    • 22944469767 scopus 로고    scopus 로고
    • Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes
    • DOI 10.1124/dmd.104.003475
    • Lim HK, Duczak N Jr, Brougham L, Elliot M, Patel K, and Chan K (2005) Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes. Drug Metab Dispos 33:1211-1219. (Pubitemid 41043765)
    • (2005) Drug Metabolism and Disposition , vol.33 , Issue.8 , pp. 1211-1219
    • Lim, H.-K.1    Duczak Jr., N.2    Brougham, L.3    Elliot, M.4    Patel, K.5    Chan, K.6
  • 25
    • 0033941434 scopus 로고    scopus 로고
    • Metabolism of ticlopidine by activated neutrophils: Implications for ticlopidine-induced agranulocytosis
    • Liu ZC and Uetrecht JP (2000) Metabolism of ticlopidine by activated neutrophils: implications for ticlopidine-induced agranulocytosis. Drug Metab Dispos 28:726-730. (Pubitemid 30470819)
    • (2000) Drug Metabolism and Disposition , vol.28 , Issue.7 , pp. 726-730
    • Liu, Z.C.1    Uetrecht, J.P.2
  • 27
    • 0027326685 scopus 로고
    • An investigation into the formation of stable, protein-reactive and cytotoxic metabolites from tacrine in vitro. Studies with human and rat liver microsomes
    • DOI 10.1016/0006-2952(93)90342-T
    • Madden S, Woolf TF, Pool WF, and Park BK (1993) An investigation into the formation of stable, protein-reactive and cytotoxic metabolites from tacrine in vitro. Studies with human and rat liver microsomes. Biochem Pharmacol 46:13-20. (Pubitemid 23218576)
    • (1993) Biochemical Pharmacology , vol.46 , Issue.1 , pp. 13-20
    • Madden, S.1    Woolf, T.F.2    Pool, W.F.3    Park, B.K.4
  • 28
    • 0034756188 scopus 로고    scopus 로고
    • Differential selectivity in carbamazepine-induced inactivation of cytochrome P450 enzymes in rat and human liver
    • DOI 10.1007/s002040100270
    • Masubuchi Y, Nakano T, Ose A, and Horie T (2001) Differential selectivity in carbamazepine-induced inactivation of cytochrome P450 enzymes in rat and human liver. Arch Toxicol 75:538-543. (Pubitemid 33044112)
    • (2001) Archives of Toxicology , vol.75 , Issue.9 , pp. 538-543
    • Masubuchi, Y.1    Nakano, T.2    Ose, A.3    Horie, T.4
  • 29
    • 0036785511 scopus 로고    scopus 로고
    • Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine
    • Masubuchi Y, Ose A, and Horie T (2002) Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine. Drug Metab Dispos 30:1143-1148.
    • (2002) Drug Metab Dispos , vol.30 , pp. 1143-1148
    • Masubuchi, Y.1    Ose, A.2    Horie, T.3
  • 30
    • 34047275727 scopus 로고    scopus 로고
    • Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: Correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans
    • DOI 10.1021/tx060234h
    • Masubuchi N, Makino C, and Murayama N (2007) Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans. Chem Res Toxicol 20:455-464. (Pubitemid 46548692)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.3 , pp. 455-464
    • Masubuchi, N.1    Makino, C.2    Murayama, N.3
  • 31
    • 38149126542 scopus 로고    scopus 로고
    • Sequential metabolism and bioactivation of the hepatotoxin benzbromarone: Formation of glutathione adducts from a catechol intermediate
    • McDonald MG and Rettie AE (2007) Sequential metabolism and bioactivation of the hepatotoxin benzbromarone: formation of glutathione adducts from a catechol intermediate. Chem Res Toxicol 20:1833-1842.
    • (2007) Chem Res Toxicol , vol.20 , pp. 1833-1842
    • McDonald, M.G.1    Rettie, A.E.2
  • 32
  • 34
    • 70349103856 scopus 로고    scopus 로고
    • A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding
    • Nakayama S, Atsumi R, Takakusa H, Kobayashi Y, Kurihara A, Nagai Y, Nakai D, and Okazaki O (2009) A zone classification system for risk assessment of idiosyncratic drug toxicity using daily dose and covalent binding. Drug Metab Dispos 37:1970-1977.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1970-1977
    • Nakayama, S.1    Atsumi, R.2    Takakusa, H.3    Kobayashi, Y.4    Kurihara, A.5    Nagai, Y.6    Nakai, D.7    Okazaki, O.8
  • 35
    • 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 (2009a) 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
  • 36
    • 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 (2009b) 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
  • 37
    • 53549100467 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose
    • Obach RS, Kalgutkar AS, Soglia JR, and Zhao SX (2008) Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose. Chem Res Toxicol 21:1814-1822.
    • (2008) Chem Res Toxicol , vol.21 , pp. 1814-1822
    • Obach, R.S.1    Kalgutkar, A.S.2    Soglia, J.R.3    Zhao, S.X.4
  • 38
    • 79958063692 scopus 로고    scopus 로고
    • An integrated reactive metabolite evaluation approach to assess and reduce safety risk during drug discovery and development
    • doi:10.1016/ j.cbi.2010.10.005
    • Reese M, Sakatis M, Ambroso J, Harrell A, Yang E, Chen L, Taylor M, Baines I, Zhu L, Ayrton A, et al. (2010) An integrated reactive metabolite evaluation approach to assess and reduce safety risk during drug discovery and development. Chem Biol Interact doi:10.1016/ j.cbi.2010.10.005.
    • (2010) Chem Biol Interact
    • Reese, M.1    Sakatis, M.2    Ambroso, J.3    Harrell, A.4    Yang, E.5    Chen, L.6    Taylor, M.7    Baines, I.8    Zhu, L.9    Ayrton, A.10
  • 41
    • 0028930481 scopus 로고
    • Mechanism-based enzyme inactivators
    • Silverman RB (1995) Mechanism-based enzyme inactivators. Methods Enzymol 249:240-283.
    • (1995) Methods Enzymol , vol.249 , pp. 240-283
    • Silverman, R.B.1
  • 43
    • 67649360007 scopus 로고    scopus 로고
    • Quantitative assessment of reactive metabolite formation using 35S-labeled glutathione
    • Takakusa H, Masumoto H, Makino C, Okazaki O, and Sudo K (2009) Quantitative assessment of reactive metabolite formation using 35S-labeled glutathione. Drug Metab Pharmacokinet 24:100-107.
    • (2009) Drug Metab Pharmacokinet , vol.24 , pp. 100-107
    • Takakusa, H.1    Masumoto, H.2    Makino, C.3    Okazaki, O.4    Sudo, K.5
  • 44
    • 77951435259 scopus 로고    scopus 로고
    • Metabolic bioactivation and drug-related adverse effects: Current status and future directions from a pharmaceutical research perspective
    • Tang W and Lu AY (2010) Metabolic bioactivation and drug-related adverse effects: current status and future directions from a pharmaceutical research perspective. Drug Metab Rev 42:225-249.
    • (2010) Drug Metab Rev , vol.42 , pp. 225-249
    • Tang, W.1    Lu, A.Y.2
  • 47
    • 0035147506 scopus 로고    scopus 로고
    • Prediction of a new drug's potential to cause idiosyncratic reactions
    • Uetrecht J (2001) Prediction of a new drug's potential to cause idiosyncratic reactions. Curr Opin Drug Discov Dev 4:55-59.
    • (2001) Curr Opin Drug Discov Dev , vol.4 , pp. 55-59
    • Uetrecht, J.1
  • 48
    • 33847081148 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: Current understanding
    • Uetrecht J (2007) Idiosyncratic drug reactions: current understanding. Annu Rev Pharmacol Toxicol 47:513-539.
    • (2007) Annu Rev Pharmacol Toxicol , vol.47 , pp. 513-539
    • Uetrecht, J.1
  • 49
    • 0021915755 scopus 로고
    • Reactivity and possible significance of hydroxylamine and nitroso metabolites of procainamide
    • Uetrecht JP (1985) Reactivity and possible significance of hydroxylamine and nitroso metabolites of procainamide. J Pharmacol Exp Ther 232:420-425.
    • (1985) J Pharmacol Exp Ther , vol.232 , pp. 420-425
    • Uetrecht, J.P.1
  • 50
    • 71049174955 scopus 로고    scopus 로고
    • Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins
    • Usui T, Mise M, Hashizume T, Yabuki M, and Komuro S (2009) Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. Drug Metab Dispos 37:2383-2392.
    • (2009) Drug Metab Dispos , vol.37 , pp. 2383-2392
    • Usui, T.1    Mise, M.2    Hashizume, T.3    Yabuki, M.4    Komuro, S.5
  • 51
    • 0035808203 scopus 로고    scopus 로고
    • Dipeptidyl peptidase IV is a target for covalent adduct formation with the acyl glucuronide metabolite of the anti-inflammatory drug zomepirac
    • DOI 10.1016/S0024-3205(00)00981-4, PII S0024320500009814
    • Wang M, Gorrell MD, McGaughan GW, and Dickinson RG (2001) Dipeptidyl peptidase IV is a target for covalent adduct formation with the acyl glucuronide metabolite of the anti-inflammatory drug zomepirac. Life Sci 68:785-797. (Pubitemid 32168009)
    • (2001) Life Sciences , vol.68 , Issue.7 , pp. 785-797
    • Wang, M.1    Gorrell, M.D.2    McCaughan, G.W.3    Dickinson, R.G.4
  • 52
    • 34250716928 scopus 로고    scopus 로고
    • Risk assessment for drug-drug interaction caused by metabolism-based inhibition of CYP3A using automated in vitro assay systems and its application in the early drug discovery process
    • DOI 10.1124/dmd.107.015016
    • Watanabe A, Nakamura K, Okudaira N, Okazaki O, and Sudo K (2007) Risk assessment for drug-drug interaction caused by metabolism-based inhibition of CYP3A using automated in vitro assay systems and its application in the early drug discovery process. Drug Metab Dispos 35:1232-1238. (Pubitemid 46956447)
    • (2007) Drug Metabolism and Disposition , vol.35 , Issue.7 , pp. 1232-1238
    • Watanabe, A.1    Nakamura, K.2    Okudaira, N.3    Okazaki, O.4    Sudo, K.-I.5
  • 53
    • 67649410245 scopus 로고    scopus 로고
    • Metabolic activation of nevirapine in human liver microsomes: Dehydrogenation and inactivation of cytochrome P450 3A4
    • Wen B, Chen Y, and Fitch WL (2009) Metabolic activation of nevirapine in human liver microsomes: dehydrogenation and inactivation of cytochrome P450 3A4. Drug Metab Dispos 37:1557-1562.
    • (2009) Drug Metab Dispos , vol.37 , pp. 1557-1562
    • Wen, B.1    Chen, Y.2    Fitch, W.L.3
  • 55
    • 0035663252 scopus 로고    scopus 로고
    • Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: Droloxifene and toremifene o-quinones
    • DOI 10.1021/tx010137i
    • Yao D, Zhang F, Yu L, Yang Y, van Breemen RB, and Bolton JL (2001) Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: droloxifene and toremifene o-quinones. Chem Res Toxicol 14:1643-1653. (Pubitemid 34016628)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.12 , pp. 1643-1653
    • Yao, D.1    Zhang, F.2    Yu, L.3    Yang, Y.4    Van Breemen, R.B.5    Bolton, J.L.6
  • 56
    • 52649157604 scopus 로고    scopus 로고
    • An algorithm for thorough background subtraction from high-resolution LC/MS data: Application for detection of glutathione-trapped reactive metabolites
    • Zhang H and Yang Y (2008) An algorithm for thorough background subtraction from high-resolution LC/MS data: application for detection of glutathione-trapped reactive metabolites. J Mass Spectrom 43:1181-1190.
    • (2008) J Mass Spectrom , vol.43 , pp. 1181-1190
    • Zhang, H.1    Yang, Y.2


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