591
Views
28
CrossRef citations to date
0
Altmetric
Reviews

Application of mechanism-based CYP inhibition for predicting drug–drug interactions

& , MD PhD
Pages 579-605 | Published online: 25 May 2009

Bibliography

  • Krayenbuhl JC, Vozeh S, Kondo-Oestreicher M, et al. Drug-drug interactions of new active substances: mibefradil example. Eur J Clin Pharmacol 1999;55:559-65
  • Li AP. Screening for human ADME/Tox drug properties in drug discovery. Drug Discov Today 2001;6:357-66
  • Zhou SF, Xue CC, Yu XQ, et al. Clinically important drug interactions potentially involving mechanism-based inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring. Ther Drug Monit 2007;29:687-710
  • Available from: http://drnelson.utmem.edu/CytochromeP450.html, [Access date: 26 March 2009]
  • Nebert DW, Russell DW. Clinical importance of the cytochromes P450. Lancet 2002;360:1155-62
  • Zhou SF. Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4. Curr Drug Metab 2008;9:310-22
  • Shimada T, Yamazaki H, Mimura M, et al. Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals. J Pharmacol Exp Ther 1994;270:414-23
  • Zhou SF, Di YM, Chan E, et al. Clinical pharmacogenetics and potential application in personalized medicine. Curr Drug Metab 2008;9:738-84
  • Zhou S, Chan E, Lim LY, et al. Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. Curr Drug Metab 2004;5:415-42
  • Houston JB, Galetin A. Methods for predicting in vivo pharmacokinetics using data from in vitro assays. Curr Drug Metab 2008;9:940-51
  • Obach RS, Walsky RL, Venkatakrishnan K. Mechanism-based inactivation of human cytochrome p450 enzymes and the prediction of drug-drug interactions. Drug Metab Dispos 2007;35:246-55
  • Dresser GK, Spence JD, Bailey DG. Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin Pharmacokinet 2000;38:41-57
  • Riley RJ, Grime K, Weaver R. Time-dependent CYP inhibition. Expert Opin Drug Metab Toxicol 2007;3:51-66
  • Spinler SA, Cheng JW, Kindwall KE, et al. Possible inhibition of hepatic metabolism of quinidine by erythromycin. Clin Pharmacol Ther 1995;57:89-94
  • Michalets EL, Williams CR. Drug interactions with cisapride: clinical implications. Clin Pharmacokinet 2000;39:49-75
  • Jurima-Romet M, Crawford K, Cyr T, et al. Terfenadine metabolism in human liver. In vitro inhibition by macrolide antibiotics and azole antifungals. Drug Metab Dispos 1994;22:849-57
  • Honig PK, Wortham DC, Zamani K, et al. Terfenadine-ketoconazole interaction: pharmacokinetic and electrocardiographic consequences. JAMA 1993;269:1513-8
  • Honig PK, Woosley RL, Zamani K, et al. Changes in the pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin. Clin Pharmacol Ther 1992;52:231-8
  • Williams D, Feely J. Pharmacokinetic-pharmacodynamic drug interactions with HMG-CoA reductase inhibitors. Clin Pharmacokinet 2002;41:343-70
  • Anderson JR, Nawarskas JJ. Cardiovascular drug-drug interactions. Cardiol Clin 2001;19:215-34
  • Simonsen U. Interactions between drugs for erectile dysfunction and drugs for cardiovascular disease. Int J Impot Res 2002;14:178-88
  • Spina E, Pisani F, Perucca E. Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet 1996;31:198-214
  • Rathbun RC, Rossi DR. Low-dose ritonavir for protease inhibitor pharmacokinetic enhancement. Ann Pharmacother 2002;36:702-6
  • Kempf DJ, Marsh KC, Kumar G, et al. Pharmacokinetic enhancement of inhibitors of the human immunodeficiency virus protease by coadministration with ritonavir. Antimicrob Agents Chemother 1997;41:654-60
  • Liebler DC, Guengerich FP. Elucidating mechanisms of drug-induced toxicity. Nat Rev Drug Discov 2005;4:410-20
  • Chitturi S, George J. Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs. Semin Liver Dis 2002;22:169-83
  • Tornqvist M, Fred C, Haglund J, et al. Protein adducts: quantitative and qualitative aspects of their formation, analysis and applications. J Chromatogr B Analyt Technol Biomed Life Sci 2002;778:279-308
  • Cohen SD, Pumford NR, Khairallah EA, et al. Selective protein covalent binding and target organ toxicity. Toxicol Appl Pharmacol 1997;143:1-12
  • Lin JH, Lu AYH. Inhibition and induction of cytochrome P450 and the clinical implications. Clin Pharmacokinet 1998;35:361-90
  • Fontana E, Dansette PM, Poli SM. Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab 2005;6:413-54
  • Zhou S, Yung Chan S, Cher Goh B, et al. Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet 2005;44:279-304
  • Voorman RL, Maio SM, Hauer MJ, et al. Metabolism of delavirdine, a human immunodeficiency virus type-1 reverse transcriptase inhibitor, by microsomal cytochrome P450 in humans, rats, and other species: probable involvement of CYP2D6 and CYP3A. Drug Metab Dispos 1998;26:631-9
  • Schrag ML, Wienkers LC. Covalent alteration of the CYP3A4 active site: evidence for multiple substrate binding domains. Arch Biochem Biophys 2001;391:49-55
  • Franklin MR. Cytochrome P450 metabolic intermediate complexes from macrolide antibiotics and related compounds. Methods Enzymol 1991;206:559-73
  • Lillibridge JH, Liang BH, Kerr BM, et al. Characterization of the selectivity and mechanism of human cytochrome P450 inhibition by the human immunodeficiency virus-protease inhibitor nelfinavir mesylate. Drug Metab Dispos 1998;26:609-16
  • Venkatakrishnan K, Obach RS, Rostami-Hodjegan A. Mechanism-based inactivation of human cytochrome P450 enzymes: strategies for diagnosis and drug-drug interaction risk assessment. Xenobiotica 2007;37:1225-56
  • Venkatakrishnan K, Obach RS. 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 2007;8:449-62
  • Kalgutkar AS, Obach RS, Maurer TS. 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 2007;8:407-47
  • Ghanbari F, Rowland-Yeo K, Bloomer JC, et al. 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 2006;7:315-34
  • Silverman RB. Mechanism-based enzyme inactivation: chemistry and enzymology. Boca Raton, FL: CRC Press; 1998
  • Wilson RC, Kitzman JV, Kemp DT, et al. Compartmental and noncompartmental pharmacokinetic analyses of minocycline hydrochloride in the dog. Am J Vet Res 1985;46:1316-8
  • Tudela J, Garcia Canovas F, Varon R, et al. Transient-phase kinetics of enzyme inactivation induced by suicide substrates. Biochim Biophys Acta 1987;912:408-16
  • Mayhew BS, Jones DR, Hall SD. An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos 2000;28:1031-7
  • Obach RS, Walsky RL, Venkatakrishnan K, et al. The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J Pharmacol Exp Ther 2006;316:336-48
  • Fairman DA, Collins C, Chapple S. Progress curve analysis of CYP1A2 inhibition: a more informative approach to the assessment of mechanism-based inactivation? Drug Metab Dispos 2007;35:2159-65
  • Dash C, Phadtare S, Deshpande V, et al. Structural and mechanistic insight into the inhibition of aspartic proteases by a slow-tight binding inhibitor from an extremophilic Bacillus sp.: correlation of the kinetic parameters with the inhibitor induced conformational changes. Biochemistry 2001;40:11525-32
  • Austin RP, Barton P, Cockroft SL, et al. The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties. Drug Metab Dispos 2002;30:1497-503
  • Wienkers LC, Heath TG. Predicting in vivo drug interactions from in vitro drug discovery data. Nat Rev Drug Discov 2005;4:825-33
  • Ito K, Iwatsubo T, Kanamitsu S, et al. Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver. Pharmacol Rev 1998;50:387-411
  • Youdim KA, Zayed A, Dickins M, et al. Application of CYP3A4 in vitro data to predict clinical drug-drug interactions; predictions of compounds as objects of interaction. Br J Clin Pharmacol 2008;65:680-92
  • Brown HS, Galetin A, Hallifax D, et al. Prediction of in vivo drug-drug interactions from in vitro data: factors affecting prototypic drug-drug interactions involving CYP2C9, CYP2D6 and CYP3A4. Clin Pharmacokinet 2006;45:1035-50
  • Waley SG. Kinetics of suicide substrates. Practical procedures for determining parameters. Biochem J 1985;227:843-9
  • Correia MA. Cytochrome P450 turnover. Methods Enzymol 1991;206:315-25
  • Wilkinson GR, Shand DG. Commentary: a physiological approach to hepatic drug clearance. Clin Pharmacol Ther 1975;18:377-90
  • Houston JB. Drug metabolite kinetics. Pharmacol Ther 1982;15:521-52
  • Ito K, Hallifax D, Obach RS, et al. Impact of parallel pathways of drug elimination and multiple cytochrome P450 involvement on drug-drug interactions: CYP2D6 paradigm. Drug Metab Dispos 2005;33:837-44
  • Kanamitsu S, Ito K, Green CE, et al. Prediction of in vivo interaction between triazolam and erythromycin based on in vitro studies using human liver microsomes and recombinant human CYP3A4. Pharm Res 2000;17:419-26
  • Davies B, Morris T. Physiological parameters in laboratory animals and humans. Pharm Res 1993;10:1093-5
  • Rostami-Hodjegan A, Tucker GT. ‘In silico’ simulations to assess the ‘in vivo’ consequences of ‘in vitro’ metabolic drug-drug interactions. Drug Discov Today Tech 2004;1:441-8
  • Galetin A, Burt H, Gibbons L, et al. Prediction of time-dependent CYP3A4 drug-drug interactions: impact of enzyme degradation, parallel elimination pathways, and intestinal inhibition. Drug Metab Dispos 2006;34:166-75
  • Thummel KE, Wilkinson GR. In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 1998;38:389-430
  • Yang J, Jamei M, Yeo KR, et al. Theoretical assessment of a new experimental protocol for determining kinetic values describing mechanism (time)-based enzyme inhibition. Eur J Pharm Sci 2007;31:232-41
  • Grime KH, Bird J, Ferguson D, et al. 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 2009;36:175-91
  • Rodrigues AD, Wong SL. Application of human liver microsomes in metabolism-based drug-drug interactions: in vitro-in vivo correlations and the Abbott Laboratories experience. Adv Pharmacol 1997;43:65-101
  • Azie NE, Brater DC, Becker PA, et al. The interaction of diltiazem with lovastatin and pravastatin. Clin Pharmacol Ther 1998;64:369-77
  • Backman JT, Olkkola KT, Aranko K, et al. Dose of midazolam should be reduced during diltiazem and verapamil treatments. Br J Clin Pharmacol 1994;37:221-5
  • Laganière S, Davies RF, Carignan G, et al. Pharmacokinetic and pharmacodynamic interactions between diltiazem and quinidine. Clin Pharmacol Ther 1996;60:255-64
  • Gorski JC, Jones DR, Haehnerdaniels BD, et al. The contribution of intestinal and hepatic CYP3A to the interaction between midazolam and clarithromycin. Clin Pharmacol Ther 1998;64:133-43
  • Greenblatt DJ, Preskorn SH, Cotreau MM, et al. Fluoxetine impairs clearance of alprazolam but not of clonazepam. Clin Pharmacol Ther 1992;52:479-86
  • Chien JY, Thummel KE, Slattery JT. Pharmacokinetic consequences of induction of CYP2E1 by ligand stabilization. Drug Metab Dispos 1997;25:1165-75
  • Wang YH, Jones DR, Hall SD. Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos 2004;32:259-66
  • Lamberg TS, Kivisto KT, Neuvonen PJ. Effects of verapamil and diltiazem on the pharmacokinetics and pharmacodynamics of buspirone. Clin Pharmacol Ther 1998;63:640-5
  • Kantola T, Kivisto KT, Neuvonen PJ. Erythromycin and verapamil considerably increase serum simvastatin and simvastatin acid concentrations. Clin Pharmacol Ther 1998;64:177-82
  • Lampen A, Christians U, Guengerich FP, et al. Metabolism of the immunosuppressant tacrolimus in the small intestine: cytochrome P450, drug interactions, and interindividual variability. Drug Metab Dispos 1995;23:1315-24
  • Ma B, Prueksaritanont T, Lin JH. Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos 2000;28:125-30
  • Schuetz EG, Beck WT, Schuetz JD. Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol 1996;49:311-8
  • Venkatakrishnan K, Obach RS. In vitro-in vivo extrapolation of CYP2D6 inactivation by paroxetine: prediction of nonstationary pharmacokinetics and drug interaction magnitude. Drug Metab Dispos 2005;33:845-52
  • Lu P, Schrag ML, Slaughter DE, et al. Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos 2003;31:1352-60
  • Karjalainen MJ, Neuvonen PJ, Backman JT. Rofecoxib is a potent, metabolism-dependent inhibitor of CYP1A2: implications for in vitro prediction of drug interactions. Drug Metab Dispos 2006;34:2091-6
  • Backman JT, Karjalainen MJ, Neuvonen M, et al. Rofecoxib is a potent inhibitor of cytochrome P450 1A2: studies with tizanidine and caffeine in healthy subjects. Br J Clin Pharmacol 2006;62:345-57
  • Bachmann K, White D, Jauregui L, et al. An evaluation of the dose-dependent inhibition of CYP1A2 by rofecoxib using theophylline as a CYP1A2 probe. J Clin Pharmacol 2003;43:1082-90
  • Heydari A, Yeo KR, Lennard MS, et al. Mechanism-based inactivation of CYP2D6 by methylenedioxymethamphetamine. Drug Metab Dispos 2004;32:1213-7
  • O'Mathuna B, Farre M, Rostami-Hodjegan A, et al. The consequences of 3, 4-methylenedioxymethamphetamine induced CYP2D6 inhibition in humans. J Clin Psychopharmacol 2008;28:523-9
  • Yang J, Jamei M, Heydari A, et al. Implications of mechanism-based inhibition of CYP2D6 for the pharmacokinetics and toxicity of MDMA. J Psychopharmacol 2006;20:842-9
  • Fahmi OA, Maurer TS, Kish M, et al. A combined model for predicting CYP3A4 clinical net drug-drug interaction based on CYP3A4 inhibition, inactivation, and induction determined in vitro. Drug Metab Dispos 2008;36:1698-708
  • Tucker GT, Houston JB, Huang SM. Optimizing drug development: strategies to assess drug metabolism/transporter interaction potential - Towards a consensus. Br J Clin Pharmacol 2001;52:107-17
  • Bjornsson TD, Callaghan JT, Einolf HJ, 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;31:815-32
  • Liston HL, DeVane CL, Boulton DW, et al. Differential time course of cytochrome P450 2D6 enzyme inhibition by fluoxetine, sertraline, and paroxetine in healthy volunteers. J Clin Psychopharmacol 2002;22:169-73
  • Tornio A, Niemi M, Neuvonen M, et al. The effect of gemfibrozil on repaglinide pharmacokinetics persists for at least 12 h after the dose: evidence for mechanism-based inhibition of CYP2C8 in vivo. Clin Pharmacol Ther 2008;84:403-11
  • Orlando R, De Martin S, Pegoraro P, et al. Irreversible CYP3A inhibition accompanied by plasma protein-binding displacement: a comparative analysis in subjects with normal and impaired liver function. Clin Pharmacol Ther 2009;85:319-26
  • Tonn GR, Wong SG, Wong SC, et al. An inhibitory metabolite leads to dose- and time-dependent pharmacokinetics of (R)-N-{1-[3-(4-ethoxy-phenyl)-4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-y l]-ethyl}-N-pyridin-3-yl-methyl-2-(4-trifluoromethoxy-phenyl)-acetamide (AMG 487) in human subjects after multiple dosing. Drug Metab Dispos 2009;37:502-13
  • Tsao S-C, Dickinson TH, Abernethy DR. Metabolite inhibition of parent drug biotransformation. Studies of diltiazem. Drug Metab Dispos 1990;18:180-2
  • Bartkowski RR, Goldberg ME, Larijani GE, et al. Inhibition of alfentanil metabolism by erythromycin. Clin Pharmacol Ther 1989;46:99-102
  • Mullins ME, Horowitz Z, Linden DHJ, et al. Life-threatening interaction of mibefradil and beta-blockers with dihydropyridine calcium channel blockers. JAMA 1998;280:157-8
  • Prueksaritanont T, Ma B, Tang C, et al. Metabolic interactions between mibefradil and HMG-CoA reductase inhibitors: an in vitro investigation with human liver preparations. Br J Clin Pharmacol 1999;47:291-8
  • Zhou SF. Potential strategies for minimizing mechanism-based inhibition of cytochrome P450 3A4. Curr Pharm Des 2008;14:990-1000
  • Tang W, Stearns RA, Wang RW, et al. Assessing and minimizing time-dependent inhibition of cytochrome P450 3A in drug discovery: a case study with melanocortin-4 receptor agonists. Xenobiotica 2008;38:1437-51
  • Jones DR, Ekins S, Li L, et al. Computational approaches that predict metabolic intermediate complex formation with CYP3A4 (+b5). Drug Metab Dispos 2007;35:1466-75
  • Zhou SF. Polymorphism of human cytochrome P450 2D6 and its clinical significance. Drug Metab Rev 2009 (accepted)
  • Yang J, Liao M, Shou M, et al. Cytochrome p450 turnover: regulation of synthesis and degradation, methods for determining rates, and implications for the prediction of drug interactions. Curr Drug Metab 2008;9:384-94

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.