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Volumn 39, Issue 12, 2011, Pages 2283-2289

CYP2C19 progress curve analysis and mechanism-based inactivation by three methylenedioxyphenyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BENZODIOXOLE DERIVATIVE; BULBOCAPNINE; CANADINE; CYTOCHROME P450 2C19; ISONIAZID; PROTOPINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TRANYLCYPROMINE;

EID: 81855206601     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.041319     Document Type: Article
Times cited : (13)

References (39)
  • 1
    • 0000178269 scopus 로고
    • Suicide enzyme inactivators
    • Abeles RH and Maycock AL (1976) Suicide enzyme inactivators. Acc Chem Res 9:313-319.
    • (1976) Acc Chem Res , vol.9 , pp. 313-319
    • Abeles, R.H.1    Maycock, A.L.2
  • 2
    • 0037369622 scopus 로고    scopus 로고
    • Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: Comparison with fluoxetine and quinidine
    • DOI 10.1124/dmd.31.3.289
    • Bertelsen KM, Venkatakrishnan K, Von Moltke LL, Obach RS, and Greenblatt DJ (2003) Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: comparison with fluoxetine and quinidine. Drug Metab Dispos 31:289-293. (Pubitemid 36249683)
    • (2003) Drug Metabolism and Disposition , vol.31 , Issue.3 , pp. 289-293
    • Bertelsen, K.M.1    Venkatakrishnan, K.2    Von Moltke, L.L.3    Obach, R.S.4    Greenblatt, D.J.5
  • 3
    • 0014853596 scopus 로고
    • Mixed-function oxidase involvement in the biochemistry of insecticide synergists
    • Casida JE (1970) Mixed-function oxidase involvement in the biochemistry of insecticide synergists. J Agric Food Chem 18:753-772.
    • (1970) J Agric Food Chem , vol.18 , pp. 753-772
    • Casida, J.E.1
  • 5
    • 0031430539 scopus 로고    scopus 로고
    • Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19
    • DOI 10.1016/S0009-9236(97)90054-0
    • Donahue SR, Flockhart DA, Abernethy DR, and Ko JW (1997) Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19. Clin Pharmacol Ther 62:572-577. (Pubitemid 28214936)
    • (1997) Clinical Pharmacology and Therapeutics , vol.62 , Issue.5 , pp. 572-577
    • Donahue, S.K.1    Flockhart, D.A.2    Abernethy, D.R.3    Ko, J.-W.4
  • 6
    • 24944510505 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes mechanism based inhibitors: Common sub-structures and reactivity
    • DOI 10.2174/138920005774330639
    • Fontana E, Dansette PM, and Poli SM (2005) Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab 6:413-454. (Pubitemid 41300789)
    • (2005) Current Drug Metabolism , vol.6 , Issue.5 , pp. 413-454
    • Fontana, E.1    Dansette, P.M.2    Poli, S.M.3
  • 7
    • 0015157025 scopus 로고
    • The enzymic formation of methylenedioxyphenyl derivative exhibiting an isocyanide-like spectrum with reduced cytochrome P-450 in hepatic microsomes
    • Franklin MR (1971) The enzymic formation of methylenedioxyphenyl derivative exhibiting an isocyanide-like spectrum with reduced cytochrome P-450 in hepatic microsomes. Xenobiotica 1:581-591.
    • (1971) Xenobiotica , vol.1 , pp. 581-591
    • Franklin, M.R.1
  • 8
    • 0025991541 scopus 로고
    • Determination of the mechanism of demethylenation of (methylenedioxy) phenyl compounds by cytochrome P450 using deuterium isotope effects
    • Fukuto JM, Kumagai Y, and Cho AK (1991) Determination of the mechanism of demethylenation of (methylenedioxy)phenyl compounds by cytochrome P450 using deuterium isotope effects. J Med Chem 34:2871-2876.
    • (1991) J Med Chem , vol.34 , pp. 2871-2876
    • Fukuto, J.M.1    Kumagai, Y.2    Cho, A.K.3
  • 9
    • 33645980647 scopus 로고    scopus 로고
    • A critical evaluation of the experimental design of studies of mechanism based enzyme inhibition, with implications for in vitro-in vivo extrapolation
    • Ghanbari F, Rowland-Yeo K, Bloomer JC, Clarke SE, Lennard MS, Tucker GT, and Rostami-Hodjegan A (2006) A critical evaluation of the experimental design of studies of mechanism based enzyme inhibition, with implications for in vitro-in vivo extrapolation. Curr Drug Metab 7:315-334.
    • (2006) Curr Drug Metab , vol.7 , pp. 315-334
    • Ghanbari, F.1    Rowland-Yeo, K.2    Bloomer, J.C.3    Clarke, S.E.4    Lennard, M.S.5    Tucker, G.T.6    Rostami-Hodjegan, A.7
  • 10
    • 79955464442 scopus 로고    scopus 로고
    • Capillary electrophoresis of phytochemical substances in herbal drugs and medicinal plants
    • Gotti R (2011) Capillary electrophoresis of phytochemical substances in herbal drugs and medicinal plants. J Pharm Biomed Anal 55:775-801.
    • (2011) J Pharm Biomed Anal , vol.55 , pp. 775-801
    • Gotti, R.1
  • 11
    • 58149242547 scopus 로고    scopus 로고
    • Mechanism-based inhibition of cytochrome P450 enzymes: An evaluation of early decision making in vitro approaches and drug-drug interaction prediction methods
    • Grime KH, Bird J, Ferguson D, and Riley RJ (2009) Mechanism-based inhibition of cytochrome P450 enzymes: an evaluation of early decision making in vitro approaches and drug-drug interaction prediction methods. Eur J Pharm Sci 36:175-191.
    • (2009) Eur J Pharm Sci , vol.36 , pp. 175-191
    • Grime, K.H.1    Bird, J.2    Ferguson, D.3    Riley, R.J.4
  • 12
    • 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
  • 13
    • 38949094492 scopus 로고    scopus 로고
    • Cytochrome p450 and chemical toxicology
    • Guengerich FP (2008) Cytochrome p450 and chemical toxicology. Chem Res Toxicol 21:70-83.
    • (2008) Chem Res Toxicol , vol.21 , pp. 70-83
    • Guengerich, F.P.1
  • 14
    • 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
  • 15
    • 0018975998 scopus 로고
    • The characterization of an inhibitory complex formed with cytochrome P-450 and a metabolite of 1,1-disubstituted hydrazines
    • Hines RN and Prough RA (1980) The characterization of an inhibitory complex formed with cytochrome P-450 and a metabolite of 1,1-disubstituted hydrazines. J Pharmacol Exp Ther 214:80-86. (Pubitemid 10032386)
    • (1980) Journal of Pharmacology and Experimental Therapeutics , vol.214 , Issue.1 , pp. 80-86
    • Hines, R.N.1    Prough, R.A.2
  • 16
    • 77955552724 scopus 로고    scopus 로고
    • Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids
    • Jadhav VB, Nayak SK, Row TN, and Kulkarni MV (2010) Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids. Eur J Med Chem 45:3575-3580.
    • (2010) Eur J Med Chem , vol.45 , pp. 3575-3580
    • Jadhav, V.B.1    Nayak, S.K.2    Row, T.N.3    Kulkarni, M.V.4
  • 17
    • 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
  • 18
    • 0034869034 scopus 로고    scopus 로고
    • Mechanism-based inactivators as probes of cytochrome P450 structure and function
    • DOI 10.2174/1389200013338478
    • Kent UM, Juschyshyn MI, and Hollenberg PF (2001) Mechanism-based inactivators as probes of cytochrome P450 structure and function. Curr Drug Metab 2:215-243. (Pubitemid 32782795)
    • (2001) Current Drug Metabolism , vol.2 , Issue.3 , pp. 215-243
    • Kent, U.M.1    Jushchyshyn, M.I.2    Hollenberg, P.F.3
  • 19
    • 79951583350 scopus 로고    scopus 로고
    • Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: A re-evaluation of P450 isoform selectivity
    • Khojasteh SC, Prabhu S, Kenny JR, Halladay JS, and Lu AY (2011) Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: a re-evaluation of P450 isoform selectivity. Eur J Drug Metab Pharmacokinet 36:1-16.
    • (2011) Eur J Drug Metab Pharmacokinet , vol.36 , pp. 1-16
    • Khojasteh, S.C.1    Prabhu, S.2    Kenny, J.R.3    Halladay, J.S.4    Lu, A.Y.5
  • 20
    • 0019488808 scopus 로고
    • Mechanism of the inhibitory action of isoniazid on microsomal drug metabolism
    • DOI 10.1016/0006-2952(81)90393-2
    • Muakkassah SF, Bidlack WR, and Yang WC (1981) Mechanism of the inhibitory action of isoniazid on microsomal drug metabolism. Biochem Pharmacol 30:1651-1658. (Pubitemid 11072297)
    • (1981) Biochemical Pharmacology , vol.30 , Issue.12 , pp. 1651-1658
    • Muakkassah, S.F.1    Bidlack, W.R.2    Yang, W.C.T.3
  • 21
    • 0034232506 scopus 로고    scopus 로고
    • Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation
    • Murray M (2000) Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation. Curr Drug Metab 1:67-84.
    • (2000) Curr Drug Metab , vol.1 , pp. 67-84
    • Murray, M.1
  • 22
    • 81855202501 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human CYP1A2 and CYP2C19 mediated metabolism by isoniazid
    • Nishimura Y, Kurata N, Iwase M, and Yasuhara H (2003) Mechanism-based inactivation of human CYP1A2 and CYP2C19 mediated metabolism by isoniazid. Drug Metab Rev 35:100.
    • (2003) Drug Metab Rev , vol.35 , pp. 100
    • Nishimura, Y.1    Kurata, N.2    Iwase, M.3    Yasuhara, H.4
  • 24
    • 34548283499 scopus 로고    scopus 로고
    • In vitro approaches to investigate mechanism-based inactivation of CYP enzymes
    • DOI 10.1517/17425255.3.3.321
    • Polasek TM and Miners JO (2007) In vitro approaches to investigate mechanism-based inactivation of CYP enzymes. Expert Opin Drug Metab Toxicol 3:321-329. (Pubitemid 47316027)
    • (2007) Expert Opinion on Drug Metabolism and Toxicology , vol.3 , Issue.3 , pp. 321-329
    • Polasek, T.M.1    Miners, J.O.2
  • 25
    • 0036223831 scopus 로고    scopus 로고
    • Summary of information on human CYP enzymes: Human P450 metabolism data
    • Rendic S (2002) Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev 34:83-448.
    • (2002) Drug Metab Rev , vol.34 , pp. 83-448
    • Rendic, S.1
  • 30
    • 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
  • 31
    • 0035119491 scopus 로고    scopus 로고
    • In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene
    • Taavitsainen P, Juvonen R, and Pelkonen O (2001) In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos 29:217-222. (Pubitemid 32179519)
    • (2001) Drug Metabolism and Disposition , vol.29 , Issue.3 , pp. 217-222
    • Taavitsainen, P.1    Juvonen, R.2    Pelkonen, O.3
  • 33
    • 79751517559 scopus 로고    scopus 로고
    • The chemical and biological properties of protopine and allocryptopine
    • Vacek J, Walterova D, Vrublova E, and Simanek V (2010) The chemical and biological properties of protopine and allocryptopine. Heterocycles 81:1773-1789.
    • (2010) Heterocycles , vol.81 , pp. 1773-1789
    • Vacek, J.1    Walterova, D.2    Vrublova, E.3    Simanek, V.4
  • 34
    • 34548738229 scopus 로고    scopus 로고
    • Drug-drug interactions via mechanism-based cytochrome P450 inactivation: Points to consider for risk assessment from in vitro data and clinical pharmacologic evaluation
    • DOI 10.2174/138920007780866861
    • Venkatakrishnan K and Obach RS (2007) Drug-drug interactions via mechanism-based cytochrome P450 inactivation: points to consider for risk assessment from in vitro data and clinical pharmacologic evaluation. Curr Drug Metab 8:449-462. (Pubitemid 47603409)
    • (2007) Current Drug Metabolism , vol.8 , Issue.5 , pp. 449-462
    • Venkatakrishnan, K.1    Obach, R.S.2
  • 35
    • 79955484651 scopus 로고    scopus 로고
    • Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR
    • Vrba J, Vrublova E, Modriansky M, and Ulrichova J (2011) Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett 203:135-141.
    • (2011) Toxicol Lett , vol.203 , pp. 135-141
    • Vrba, J.1    Vrublova, E.2    Modriansky, M.3    Ulrichova, J.4
  • 37
    • 62349108804 scopus 로고    scopus 로고
    • Structure of cytochrome p450s and personalized drug
    • Wang JF, Zhang CC, Chou KC, and Wei DQ (2009) Structure of cytochrome p450s and personalized drug. Curr Med Chem 16:232-244.
    • (2009) Curr Med Chem , vol.16 , pp. 232-244
    • Wang, J.F.1    Zhang, C.C.2    Chou, K.C.3    Wei, D.Q.4
  • 38
    • 27644596457 scopus 로고    scopus 로고
    • Predicting in vivo drug interactions from in vitro drug discovery data
    • DOI 10.1038/nrd1851, PII N1851
    • Wienkers LC and Heath TG (2005) Predicting in vivo drug interactions from in vitro drug discovery data. Nat Rev Drug Discov 4:825-833. (Pubitemid 41553963)
    • (2005) Nature Reviews Drug Discovery , vol.4 , Issue.10 , pp. 825-833
    • Wienkers, L.C.1    Heath, T.G.2


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