메뉴 건너뛰기




Volumn 63, Issue 2, 2011, Pages 214-221

Mechanism of cytochrome P450-3A inhibition by ketoconazole

Author keywords

competitive inhibition; cytochrome P450 3A; ketoconazole; mechanism based inhibition; noncompetitive inhibition

Indexed keywords

ANDROSTENEDIONE; CYTOCHROME P450 3A; DIAZEPAM; KETOCONAZOLE; MIDAZOLAM; NIFEDIPINE; PHENACETIN; TESTOSTERONE; TRIAZOLAM; TROLEANDOMYCIN;

EID: 78751483916     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.2010.01202.x     Document Type: Article
Times cited : (96)

References (40)
  • 1
    • 0034004083 scopus 로고    scopus 로고
    • Effects of the antifungal agents on oxidative drug metabolism in humans: Clinical relevance
    • Venkatakrishnan K, et al. Effects of the antifungal agents on oxidative drug metabolism in humans: clinical relevance. Clin Pharmacokinet 2000; 38: 111-180.
    • (2000) Clin Pharmacokinet , vol.38 , pp. 111-180
    • Venkatakrishnan, K.1
  • 4
    • 77956592952 scopus 로고    scopus 로고
    • Sources of variability in ketoconazole inhibition of human cytochrome P450 3A in vitro
    • Greenblatt DJ, et al. Sources of variability in ketoconazole inhibition of human cytochrome P450 3A in vitro. Xenobiotica 2010; 40: 713-720.
    • (2010) Xenobiotica , vol.40 , pp. 713-720
    • Greenblatt, D.J.1
  • 5
    • 10044251943 scopus 로고    scopus 로고
    • Modelling atypical CYP3A4 kinetics: Principles and pragmatism
    • Houston JB, Galetin A,. Modelling atypical CYP3A4 kinetics: principles and pragmatism. Arch Biochem Biophys 2005; 433: 351-360.
    • (2005) Arch Biochem Biophys , vol.433 , pp. 351-360
    • Houston, J.B.1    Galetin, A.2
  • 6
    • 0032735988 scopus 로고    scopus 로고
    • CYP3A4 drug interactions: Correlation of 10 in vitro probe substrates
    • Kenworthy KE, et al. CYP3A4 drug interactions: correlation of 10 in vitro probe substrates. Br J Clin Pharmacol 1999; 48: 716-727.
    • (1999) Br J Clin Pharmacol , vol.48 , pp. 716-727
    • Kenworthy, K.E.1
  • 7
    • 0027326229 scopus 로고
    • Alprazolam metabolism in vitro: Studies of human, monkey, mouse, and rat liver microsomes
    • von Moltke LL, et al. Alprazolam metabolism in vitro: studies of human, monkey, mouse, and rat liver microsomes. Pharmacology 1993; 47: 268-276.
    • (1993) Pharmacology , vol.47 , pp. 268-276
    • Von Moltke, L.L.1
  • 8
    • 0037974573 scopus 로고    scopus 로고
    • In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes P450: Role of CYP3A4 and CYP3A5
    • Patki KC, et al. In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes P450: role of CYP3A4 and CYP3A5. Drug Metab Dispos 2003; 31: 938-944.
    • (2003) Drug Metab Dispos , vol.31 , pp. 938-944
    • Patki, K.C.1
  • 9
    • 0042357511 scopus 로고    scopus 로고
    • Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: Midazolam, testosterone, and nifedipine
    • Galetin A, et al. Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: midazolam, testosterone, and nifedipine. Drug Metab Dispos 2003; 31: 1108-1116.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1108-1116
    • Galetin, A.1
  • 10
    • 0030077245 scopus 로고    scopus 로고
    • Triazolam biotransformation by human liver microsomes in vitro: Effects of metabolic inhibitors, and clinical confirmation of a predicted interaction with ketoconazole
    • von Moltke LL, et al. Triazolam biotransformation by human liver microsomes in vitro: effects of metabolic inhibitors, and clinical confirmation of a predicted interaction with ketoconazole. J Pharmacol Exp Ther 1996; 276: 370-379.
    • (1996) J Pharmacol Exp Ther , vol.276 , pp. 370-379
    • Von Moltke, L.L.1
  • 11
    • 0033979574 scopus 로고    scopus 로고
    • Midazolam and triazolam biotransformation in mouse and human liver microsomes: Relative contribution of CYP3A and CYP2C isoforms
    • Perloff MD, et al. Midazolam and triazolam biotransformation in mouse and human liver microsomes: relative contribution of CYP3A and CYP2C isoforms. J Pharmacol Exp Ther 2000; 292: 618-628.
    • (2000) J Pharmacol Exp Ther , vol.292 , pp. 618-628
    • Perloff, M.D.1
  • 12
    • 0029743080 scopus 로고    scopus 로고
    • Midazolam hydroxylation by human liver microsomes in vitro: Inhibition by fluoxetine, norfluoxetine, and by azole antifungal agents
    • von Moltke LL, et al. Midazolam hydroxylation by human liver microsomes in vitro: inhibition by fluoxetine, norfluoxetine, and by azole antifungal agents. J Clin Pharmacol 1996; 36: 783-791.
    • (1996) J Clin Pharmacol , vol.36 , pp. 783-791
    • Von Moltke, L.L.1
  • 13
    • 0003518480 scopus 로고
    • New York: John Wiley and Sons
    • Segel IH,. Enzyme Kinetics. New York: John Wiley and Sons, 1975.
    • (1975) Enzyme Kinetics
    • Segel, I.H.1
  • 14
    • 0034770465 scopus 로고    scopus 로고
    • Human drug metabolism and the cytochromes P450: Application and relevance of in vitro models
    • Venkatakrishnan K, et al. Human drug metabolism and the cytochromes P450: application and relevance of in vitro models. J Clin Pharmacol 2001; 41: 1149-1179.
    • (2001) J Clin Pharmacol , vol.41 , pp. 1149-1179
    • Venkatakrishnan, K.1
  • 15
    • 65949099562 scopus 로고    scopus 로고
    • In vitro approaches to anticipating clinical drug interactions
    • In: Li A.P., ed. Hoboken, NJ: John Wiley & Sons
    • Volak LP, et al. In vitro approaches to anticipating clinical drug interactions. In:, Li AP, ed. Drug-Drug Interactions in Pharmaceutical Development. Hoboken, NJ: John Wiley & Sons, 2008; 75-93.
    • (2008) Drug-Drug Interactions in Pharmaceutical Development , pp. 75-93
    • Volak, L.P.1
  • 16
  • 17
    • 0035148967 scopus 로고    scopus 로고
    • Triazolam substrate inhibition: Evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site
    • Schrag ML, Wienkers LC,. Triazolam substrate inhibition: evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. Drug Metab Dispos 2001; 29: 70-75.
    • (2001) Drug Metab Dispos , vol.29 , pp. 70-75
    • Schrag, M.L.1    Wienkers, L.C.2
  • 18
    • 0029790347 scopus 로고    scopus 로고
    • Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450
    • Ghosal A, et al. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cDNA-expressed human cytochrome P450. Drug Metab Dispos 1996; 24: 940-947.
    • (1996) Drug Metab Dispos , vol.24 , pp. 940-947
    • Ghosal, A.1
  • 19
    • 0028234586 scopus 로고
    • Regioselective biotransformation of midazolam by members of the human Cytochrome P450 3A (CYP3A) subfamily
    • Gorski JC, et al. Regioselective biotransformation of midazolam by members of the human Cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 1994; 47: 1643-1653.
    • (1994) Biochem Pharmacol , vol.47 , pp. 1643-1653
    • Gorski, J.C.1
  • 20
    • 23044500208 scopus 로고    scopus 로고
    • CYP3A4 substrate selection and substitution in the prediction of potential drug-drug interactions
    • Galetin A, et al. CYP3A4 substrate selection and substitution in the prediction of potential drug-drug interactions. J Pharmacol Exp Ther 2005; 314: 180-190.
    • (2005) J Pharmacol Exp Ther , vol.314 , pp. 180-190
    • Galetin, A.1
  • 21
    • 0034705191 scopus 로고    scopus 로고
    • Elucidation of distinct ligand binding sites for cytochrome P450 3A4
    • Hosea NA, et al. Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry 2000; 39: 5929-5939.
    • (2000) Biochemistry , vol.39 , pp. 5929-5939
    • Hosea, N.A.1
  • 23
    • 0035193493 scopus 로고    scopus 로고
    • Multisite kinetic models for CYP3A4: Simultaneous activation and inhibition of diazepam and testosterone metabolism
    • Kenworthy KE, et al. Multisite kinetic models for CYP3A4: simultaneous activation and inhibition of diazepam and testosterone metabolism. Drug Metab Dispos 2001; 29: 1644-1651.
    • (2001) Drug Metab Dispos , vol.29 , pp. 1644-1651
    • Kenworthy, K.E.1
  • 24
    • 0032499691 scopus 로고    scopus 로고
    • Analysis of human cytochrome P450 3A4 cooperativity: Construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics
    • Harlow GR, Halpert JR,. Analysis of human cytochrome P450 3A4 cooperativity: construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics. Proc Natl Acad Sci USA 1998; 95: 6636-6641.
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 6636-6641
    • Harlow, G.R.1    Halpert, J.R.2
  • 25
    • 0031028518 scopus 로고    scopus 로고
    • Cooperativity in oxidations catalyzed by cytochrome P450 3A4
    • Ueng Y-F, et al. Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Biochemistry 1997; 36: 370-381.
    • (1997) Biochemistry , vol.36 , pp. 370-381
    • Ueng, Y.-F.1
  • 26
    • 33846449874 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human cytochrome P450 enzymes and the prediction of drug-drug interactions
    • Obach RS, et al. Mechanism-based inactivation of human cytochrome P450 enzymes and the prediction of drug-drug interactions. Drug Metab Dispos 2007; 35: 246-255.
    • (2007) Drug Metab Dispos , vol.35 , pp. 246-255
    • Obach, R.S.1
  • 27
    • 77955275817 scopus 로고    scopus 로고
    • Inactivation of human Cytochrome P450 enzymes and drug-drug interactions
    • In: Pang K.S. et al., eds. New York: Springer
    • Obach RS, et al. Inactivation of human Cytochrome P450 enzymes and drug-drug interactions. In:, Pang KS, et al., eds. Enzyme- and Transporter-Based Drug-Drug Interactions: Progress and Future Challenges. New York: Springer, 2010; 473-492.
    • (2010) Enzyme- And Transporter-Based Drug-Drug Interactions: Progress and Future Challenges , pp. 473-492
    • Obach, R.S.1
  • 28
    • 0037369622 scopus 로고    scopus 로고
    • Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: Comparison with fluoxetine and quinidine
    • Bertelsen KM, et al. Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: comparison with fluoxetine and quinidine. Drug Metab Dispos 2003; 31: 289-293.
    • (2003) Drug Metab Dispos , vol.31 , pp. 289-293
    • Bertelsen, K.M.1
  • 29
    • 24944510505 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes mechanism based inhibitors: Common sub-structures and reactivity
    • Fontana E, et al. Cytochrome P450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab 2005; 6: 413-454.
    • (2005) Curr Drug Metab , vol.6 , pp. 413-454
    • Fontana, E.1
  • 30
    • 0033948964 scopus 로고    scopus 로고
    • Potent mechanism-based inhibition of human CYP3A in vitro by amprenavir and ritonavir: Comparison with ketoconazole
    • von Moltke LL, et al. Potent mechanism-based inhibition of human CYP3A in vitro by amprenavir and ritonavir: comparison with ketoconazole. Eur J Clin Pharmacol 2000; 56: 259-261.
    • (2000) Eur J Clin Pharmacol , vol.56 , pp. 259-261
    • Von Moltke, L.L.1
  • 31
    • 0037357063 scopus 로고    scopus 로고
    • Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir
    • Weemhoff JL, et al. Apparent mechanism-based inhibition of human CYP3A in-vitro by lopinavir. J Pharm Pharmacol 2003; 55: 381-386.
    • (2003) J Pharm Pharmacol , vol.55 , pp. 381-386
    • Weemhoff, J.L.1
  • 32
    • 18844409566 scopus 로고    scopus 로고
    • Atazanavir: Effects on P-glycoprotein transport and CYP3A metabolism in vitro
    • Perloff ES, et al. Atazanavir: effects on P-glycoprotein transport and CYP3A metabolism in vitro. Drug Metab Dispos 2005; 33: 764-770.
    • (2005) Drug Metab Dispos , vol.33 , pp. 764-770
    • Perloff, E.S.1
  • 33
    • 73349103803 scopus 로고    scopus 로고
    • Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition
    • Sekiguchi N, et al. Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition. Drug Metab Pharmacokinet 2009; 24: 500-510.
    • (2009) Drug Metab Pharmacokinet , vol.24 , pp. 500-510
    • Sekiguchi, N.1
  • 34
    • 0028279667 scopus 로고
    • Inhibitors of alprazolam metabolism in vitro: Effect of serotonin-reuptake-inhibitor antidepressants, ketoconazole and quinidine
    • von Moltke LL, et al. Inhibitors of alprazolam metabolism in vitro: effect of serotonin-reuptake-inhibitor antidepressants, ketoconazole and quinidine. Br J Clin Pharmacol 1994; 38: 23-31.
    • (1994) Br J Clin Pharmacol , vol.38 , pp. 23-31
    • Von Moltke, L.L.1
  • 35
    • 0028568568 scopus 로고
    • In vitro prediction of the terfenadine-ketoconazole pharmacokinetic interaction
    • von Moltke LL, et al. In vitro prediction of the terfenadine-ketoconazole pharmacokinetic interaction. J Clin Pharmacol 1994; 34: 1222-1227.
    • (1994) J Clin Pharmacol , vol.34 , pp. 1222-1227
    • Von Moltke, L.L.1
  • 36
    • 47749131934 scopus 로고    scopus 로고
    • Heterotropic cooperativity in oxidation mediated by Cytochrome P450
    • Niwa T, et al. Heterotropic cooperativity in oxidation mediated by Cytochrome P450. Curr Drug Metab 2008; 9: 453-462.
    • (2008) Curr Drug Metab , vol.9 , pp. 453-462
    • Niwa, T.1
  • 37
    • 29244447987 scopus 로고    scopus 로고
    • The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions
    • Obach RS, et al. The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J Pharmacol Exp Ther 2006; 316: 336-348.
    • (2006) J Pharmacol Exp Ther , vol.316 , pp. 336-348
    • Obach, R.S.1
  • 38
    • 28844476587 scopus 로고    scopus 로고
    • In vitro cytochrome P450 inhibition data and the prediction of drug-drug interactions: Qualitative relationships, quantitative predictions, and the rank-order approach
    • Obach RS, et al. In vitro cytochrome P450 inhibition data and the prediction of drug-drug interactions: qualitative relationships, quantitative predictions, and the rank-order approach. Clin Pharmacol Ther 2005; 78: 582-592.
    • (2005) Clin Pharmacol Ther , vol.78 , pp. 582-592
    • Obach, R.S.1
  • 39
    • 36949032109 scopus 로고    scopus 로고
    • Quantitative correlations among CYP3A sensitive substrates and inhibitors: Literature analysis
    • Ragueneau-Majlessi I, et al. Quantitative correlations among CYP3A sensitive substrates and inhibitors: literature analysis. Curr Drug Metab 2007; 8: 810-814.
    • (2007) Curr Drug Metab , vol.8 , pp. 810-814
    • Ragueneau-Majlessi, I.1
  • 40
    • 10744232330 scopus 로고    scopus 로고
    • The conduct of in vitro and in vivo drug-drug interaction studies: A Pharmaceutical Research and Manufacturers of America (PhRMA) perspective
    • Bjornsson TD, et al. The conduct of in vitro and in vivo drug-drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab Dispos 2003; 31: 815-832.
    • (2003) Drug Metab Dispos , vol.31 , pp. 815-832
    • Bjornsson, T.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.