Clinically Important Drug Interactions Potentially Involving Mechanism-based Inhibition of Cytochrome P450 3A4 and the Role of Therapeutic Drug Monitoring
Tóm tắt
Từ khóa
Tài liệu tham khảo
Huang, 2007, Drug interaction studies: study design, data analysis, and implications for dosing and labeling., Clin Pharmacol Ther, 81, 298, 10.1038/sj.clpt.6100054
Plant, 2007, The human cytochrome P450 sub-family: transcriptional regulation, inter-individual variation and interaction networks., Biochim Biophys Acta, 1770, 478, 10.1016/j.bbagen.2006.09.024
Zhou, 2004, Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4., Curr Drug Metab, 5, 415, 10.2174/1389200043335450
Zhou, 2005, Drug bioactivation, covalent binding to target proteins and toxicity relevance., Drug Metab Rev, 37, 41, 10.1081/DMR-200028812
Zhou, 2005, Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs., Clin Pharmacokinet, 44, 279, 10.2165/00003088-200544030-00005
Ito, 1998, Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver., Pharmacol Rev, 50, 387
Lu, 2007, A novel model for the prediction of drug-drug interactions in humans based on in vitro cytochrome p450 phenotypic data., Drug Metab Dispos, 35, 79, 10.1124/dmd.106.011346
Galetin, 2006, Prediction of time-dependent CYP3A4 drug-drug interactions: impact of enzyme degradation, parallel elimination pathways, and intestinal inhibition., Drug Metab Dispos, 34, 166, 10.1124/dmd.105.006874
Thummel, 1998, In vitro and in vivo drug interactions involving human CYP3A., Annu Rev Pharmacol Toxicol, 38, 389, 10.1146/annurev.pharmtox.38.1.389
Yuan, 2002, Evaluation of cytochrome p450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions., Drug Metab Dispos, 30, 1311, 10.1124/dmd.30.12.1311
Kim, 1999, Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein., Pharmacol Res, 16, 408, 10.1023/A:1018877803319
Kim, 2002, Drugs as P-glycoprotein substrates, inhibitors, and inducers., Drug Metab Rev, 34, 47, 10.1081/DMR-120001389
Kurnik, 2006, The erythromycin breath test reflects P-glycoprotein function independently of cytochrome P450 3A activity., Clin Pharmacol Ther, 80, 228, 10.1016/j.clpt.2006.06.002
Yusa, 1989, Reversal mechanism of multidrug resistance by verapamil: direct binding of verapamil to P-glycoprotein on specific sites and transport of verapamil outward across the plasma membrane of K562/ADM cells., Cancer Res, 49, 5002
Kivisto, 2004, Functional interaction of intestinal CYP3A4 and P-glycoprotein., Fundam Clin Pharmacol, 18, 621, 10.1111/j.1472-8206.2004.00291.x
Ambudkar, 1999, Biochemical, cellular, and pharmacological aspects of the multidrug transporter., Annu Rev Pharmacol Toxicol, 39, 361, 10.1146/annurev.pharmtox.39.1.361
Huang, 2001, Induction of P-glycoprotein and cytochrome P450 3A by HIV protease inhibitors., Drug Metab Dispos, 29, 754
Guengerich, 1990, Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene., Chem Res Toxicol, 3, 363, 10.1021/tx00016a015
Foroozesh, 1997, Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes., Chem Res Toxicol, 10, 91, 10.1021/tx960064g
Helvig, 1997, Suicide inactivation of cytochrome P450 by midchain and terminal acetylenesa mechanistic study of inactivation of a plant acid omega-hydroxylase., J Biol Chem, 272, 414, 10.1074/jbc.272.1.414
He, 1999, Mechanism-based inactivation of cytochrome P-450-3A4 by mifepristone (RU486)., J Pharmacol Exp Ther, 288, 791
Lim, 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, 10.1124/dmd.104.003475
Bensoussan, 1995, Particular ability of cytochromes P450 3A to form inhibitory P450-iron-metabolite complexes upon metabolic oxidation of aminodrugs., Biochem Pharmacol, 49, 591, 10.1016/0006-2952(94)00477-4
Pershing, 1982, Cytochrome P-450 metabolic-intermediate complex formation and induction by macrolide antibiotics: a new class of agents., Xenobiotica, 12, 687, 10.3109/00498258209038944
Periti, 1992, Pharmacokinetic drug interactions of macrolides., Clin Pharmacokinet, 23, 106, 10.2165/00003088-199223020-00004
Ludden, 1985, Pharmacokinetic interactions of the macrolide antibiotics., Clin Pharmacokinet, 10, 63, 10.2165/00003088-198510010-00003
von Rosensteil, 1995, Macrolide antibacterials. Drug interactions of clinical significance., Drug Saf, 13, 105
Pessayre, 1983, Inactivation of cytochrome P-450 by a troleandomycin metabolite. Protective role of glutathione., J Pharmacol Exp Ther, 224, 685
Tinel, 1989, Effects of clarithromycin on cytochrome P-450. Comparison with other macrolides., J Pharmacol Exp Ther, 250, 746
Miura, 1989, Decrease in a constitutive form of cytochrome P-450 by macrolide antibiotics., J Antimicrob Chemother, 24, 551, 10.1093/jac/24.4.551
Larry, 1983, Effect of erythromycin on hepatic drug-metabolizing enzymes in humans., Biochem Pharmacol, 32, 1063, 10.1016/0006-2952(83)90626-3
Amacher, 1991, Comparison of the effects of the new azalide antibiotic, azithromycin, and erythromycin estolate on rat liver cytochrome P-450., Antimicrob Agents Chemother, 35, 1186, 10.1128/AAC.35.6.1186
Delaforge, 1983, Dual effects of macrolide antibiotics on rat liver cytochrome P-450. Induction and formation of metabolite-complexes: a structure-activity relationship., Biochem Pharmacol, 32, 2309, 10.1016/0006-2952(83)90178-8
Larrey, 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, 10.1016/0006-2952(83)90470-7
Lin, 2002, Mechanism-based inactivation of cytochrome P450 3A4 by 17 alpha-ethynylestradiol: evidence for heme destruction and covalent binding to protein., J Pharmacol Exp Ther, 301, 160, 10.1124/jpet.301.1.160
Guengerich, 1990, Metabolism of 17 alpha-ethynylestradiol in humans., Life Sci, 47, 1981, 10.1016/0024-3205(90)90431-P
Lin, 1998, Inhibition and induction of cytochrome P450 and the clinical implications., Clin Pharmacokinet, 35, 361, 10.2165/00003088-199835050-00003
Watson, 1997, Therapeutic drug monitoring., Ther Drug Monit, 19, 125, 10.1097/00007691-199704000-00001
von Moltke, 2000, Potent mechanism-based inhibition of human CYP3A in vitro by amprenavir and ritonavir: comparison with ketoconazole., Eur J Clin Pharmacol, 56, 259, 10.1007/s002280000125
Piacenti, 2006, An update and review of antiretroviral therapy., Pharmacotherapy, 26, 1111, 10.1592/phco.26.8.1111
Greenblatt, 2000, Alprazolam-ritonavir interaction: implications for product labeling., Clin Pharmacol Ther, 67, 335, 10.1067/mcp.2000.105757
Gerber, 2001, Effect of ritonavir/saquinavir on stereoselective pharmacokinetics of methadone: results of AIDS Clinical Trials Group (ACTG) 401., J Acquir Immune Defic Syndr, 27, 153, 10.1097/00042560-200106010-00010
von Moltke, 1998, Inhibition of desipramine hydroxylation (Cytochrome P450-2D6) in vitro by quinidine and by viral protease inhibitors: relation to drug interactions in vivo., J Pharm Sci, 87, 1184, 10.1021/js980197h
Knoell, 1998, Potential interaction involving warfarin and ritonavir., Ann Pharmacother, 32, 1299, 10.1345/aph.17456
Levy, 1995, Cytochrome P450 isozymes and antiepileptic drug interactions., Epilepsia, 36, S8, 10.1111/j.1528-1157.1995.tb06007.x
Komatsu, 2000, Formation of a dihydroxy metabolite of phenytoin in human liver microsomes/cytosol: roles of cytochromes P4502C9, 2C19, and 3A4., Drug Metab Dispos, 28, 1361
Yamazaki, 1997, Human liver cytochrome P450 enzymes involved in the 7-hydroxylation of R- and S-warfarin enantiomers., Biochem Pharmacol, 54, 1195, 10.1016/S0006-2952(97)00304-3
Hsu, 1998, Ritonavir. Clinical pharmacokinetics and interactions with other anti-HIV agents., Clin Pharmacokinet, 35, 275, 10.2165/00003088-199835040-00002
Malaty, 1999, Drug interactions of HIV protease inhibitors., Drug Saf, 20, 147, 10.2165/00002018-199920020-00005
Mikus, 2006, Potent cytochrome P450 2C19 genotype-related interaction between voriconazole and the cytochrome P450 3A4 inhibitor ritonavir., Clin Pharmacol Ther, 80, 126, 10.1016/j.clpt.2006.04.004
Cheng, 2002, Rhabdomyolysis due to probable interaction between simvastatin and ritonavir., Am J Health Syst Pharm, 59, 728, 10.1093/ajhp/59.8.728
Neuvonen, 2006, Drug interactions with lipid-lowering drugs: mechanisms and clinical relevance., Clin Pharmacol Ther, 80, 565, 10.1016/j.clpt.2006.09.003
Mahon, 1998, Calcium channel blockers in cardiac failure., Prog Cardiovasc Dis, 41, 191, 10.1016/S0033-0620(98)80055-8
Jones, 1999, Diltiazem inhibition of cytochrome P-450 3A activity is due to metabolite intermediate complex formation., J Pharmacol Exp Ther, 290, 1116
Tsao, 1990, Metabolite inhibition of parent drug biotransformation. Studies of diltiazem., Drug Metab Dispos, 18, 180
Azie, 1998, The interaction of diltiazem with lovastatin and pravastatin., Clin Pharmacol Ther, 64, 369, 10.1016/S0009-9236(98)90067-4
Dixit, 1999, Pharmacokinetic interaction between diltiazem and tolbutamide., Drug Metabol Drug Interact, 15, 269, 10.1515/DMDI.1999.15.4.269
Weir, 1998, Steady-state pharmacokinetics of diltiazem and hydrochlorothiazide administered alone and in combination., Biopharm Drug Dispos, 19, 365, 10.1002/(SICI)1099-081X(199809)19:6<365::AID-BDD112>3.0.CO;2-R
Stoysich, 1996, Further elucidation of pharmacokinetic interaction between diltiazem and warfarin., Int J Clin Pharmacol Ther, 34, 56
Po, 1998, What lessons can be learnt from withdrawal of mibefradil from the market?, Lancet, 351, 1829, 10.1016/S0140-6736(05)78800-0
Welker, 1998, Clinical pharmacokinetics of mibefradil., Clin Pharmacokinet, 35, 405, 10.2165/00003088-199835060-00001
Mullins, 1998, Life-threatening interaction of mibefradil and beta-blockers with dihydropyridine calcium channel blockers., JAMA, 280, 157, 10.1001/jama.280.2.157
Schmassmann-Suhijar, 1998, Rhabdomyolysis due to interaction of simvastatin with mibefradil., Lancet, 351, 1929, 10.1016/S0140-6736(05)78613-X
Muck, 2000, Metabolic interactions between mibefradil and HMG-CoA reductase inhibitors: linking in vitro with in vivo information., Br J Clin Pharmacol, 49, 87
Ereshefsky, 2005, Antidepressant drug-drug interaction profile update., Drugs R D, 6, 323, 10.2165/00126839-200506060-00002
Nieuwstraten, 2006, Systematic overview of drug interactions with antidepressant medications., Can J Psychiatry, 51, 300, 10.1177/070674370605100506
Fisher, 1998, Tamoxifen for prevention of breast cancer: report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study., J Natl Cancer Inst, 90, 1371, 10.1093/jnci/90.18.1371
Furr, 1984, The pharmacology and clinical uses of tamoxifen., Pharmacol Ther, 25, 127, 10.1016/0163-7258(84)90043-3
Benson, 2003, Update on clinical role of tamoxifen., Curr Opin Obstet Gynecol, 15, 13, 10.1097/00001703-200302000-00003
ORegan, 2002, The evolution of tamoxifen therapy in breast cancer: selective oestrogen-receptor modulators and downregulators., Lancet Oncol, 3, 207, 10.1016/S1470-2045(02)00711-8
Clemons, 2002, Tamoxifen (Nolvadex): a review., Cancer Treat Rev, 28, 165, 10.1016/S0305-7372(02)00036-1
Zhao, 2002, Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites., Xenobiotica, 32, 863, 10.1080/00498250210158230
Tenni, 1989, Life threatening interaction between tamoxifen and warfarin., BMJ, 298, 93, 10.1136/bmj.298.6666.93
Sridar, 2004, Silybin inactivates cytochromes P450 3A4 and 2C9 and inhibits major hepatic glucuronosyltransferases., Drug Metab Dispos, 32, 587, 10.1124/dmd.32.6.587
Piscitelli, 2002, Effect of Milk thistle on the pharmacokinetics of indinavir in healthy volunteers., Pharmacotherapy, 22, 551, 10.1592/phco.22.8.551.33205
Dresser, 2000, Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition., Clin Pharmacokinet, 38, 41, 10.2165/00003088-200038010-00003
Michalets, 2000, Drug interactions with cisapride: clinical implications., Clin Pharmacokinet, 39, 49, 10.2165/00003088-200039010-00004
Jurima-Romet, 1994, Terfenadine metabolism in human liver. In vitro inhibition by macrolide antibiotics and azole antifungals., Drug Metab Dispos, 22, 849
Honig, 1993, Terfenadine-ketoconazole interaction: pharmacokinetic and electrocardiographic consequences., JAMA, 269, 1513, 10.1001/jama.1993.03500120051025
Honig, 1992, Changes in the pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin., Clin Pharmacol Ther, 52, 231, 10.1038/clpt.1992.135
Williams, 2002, Pharmacokinetic-pharmacodynamic drug interactions with HMG-CoA reductase inhibitors., Clin Pharmacokinet, 41, 343, 10.2165/00003088-200241050-00003
Anderson, 2001, Cardiovascular drug-drug interactions., Cardiol Clin, 19, 215, 10.1016/S0733-8651(05)70209-5
Simonsen, 2002, Interactions between drugs for erectile dysfunction and drugs for cardiovascular disease., Int J Impot Res, 14, 178, 10.1038/sj.ijir.3900846
Patsalos, 2002, The importance of drug interactions in epilepsy therapy., Epilepsia, 43, 365, 10.1046/j.1528-1157.2002.13001.x
Spinler, 1995, Possible inhibition of hepatic metabolism of quinidine by erythromycin., Clin Pharmacol Ther, 57, 89, 10.1016/0009-9236(95)90270-8
Wen, 2002, Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes., Eur J Clin Pharmacol, 57, 799, 10.1007/s00228-001-0396-3
Kutt, 1968, Inhibition of diphenylhydantoin metabolism in rats and in rat liver microsomes by antitubercular drugs., Neurology, 18, 706, 10.1212/WNL.18.7.706
Miller, 1979, Clinical importance of the interaction of phenytoin and isoniazid: a report from the Boston Collaborative Drug Surveillance Program., Chest, 75, 356, 10.1378/chest.75.3.356
Crippin, 1993, Acetaminophen hepatotoxicity: potentiation by isoniazid., Am J Gastroenterol, 88, 590
Nolan, 1994, Hepatotoxicity associated with acetaminophen usage in patients receiving multiple drug therapy for tuberculosis., Chest, 105, 408, 10.1378/chest.105.2.408
Self, 1999, Isoniazid drug and food interactions., Am J Med Sci, 317, 304, 10.1097/00000441-199905000-00007
Venkatakrishnan, 1998, Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man., J Pharm Pharmacol, 50, 265, 10.1111/j.2042-7158.1998.tb06859.x
Patten, 1993, Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics., Chem Res Toxicol, 6, 511, 10.1021/tx00034a019
Wang, 2003, Structure-activity relationship: analyses of p-glycoprotein substrates and inhibitors., J Clin Pharmacol Ther, 28, 203, 10.1046/j.1365-2710.2003.00487.x
Pichard, 1990, Cyclosporin A drug interactions. Screening for inducers and inhibitors of cytochrome P-450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes., Drug Metab Dispos, 18, 595
Loo, 1994, Mutations to amino acids located in predicted transmembrane segment 6 (TM6) modulate the activity and substrate specificity of human P-glycoprotein., Biochemistry, 33, 14049, 10.1021/bi00251a013
Rawden, 2000, Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes., Br J Clin Pharmacol, 49, 313, 10.1046/j.1365-2125.2000.00170.x
Rendic, 1997, Human cytochrome P450 enzyme: a status report summarizing their reactions, substrates, induction, and inhibitors., Drug Metab Rev, 29, 413, 10.3109/03602539709037591
Polasek, 2004, Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro., J Pharmacol Exp Ther, 311, 996, 10.1124/jpet.104.071803
Jones, 2007, Computational approaches that predict metabolic intermediate complex formation with CYP3A4(+b5)., Drug Metab Dispos, 35, 1466, 10.1124/dmd.106.014613
Ernest, 2005, 2nd, Hall SD, Jones DR. Mechanism-based inactivation of CYP3A by HIV protease inhibitors., J Pharmacol Exp Ther, 312, 583, 10.1124/jpet.104.075416
Ito, 2003, Prediction of the in vivo interaction between midazolam and macrolides based on in vitro studies using human liver microsomes., Drug Metab Dispos, 31, 945, 10.1124/dmd.31.7.945
Mayhew, 2000, An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation., Drug Metab Dispos, 28, 1031
Polasek, 2006, Quantitative prediction of macrolide drug-drug interaction potential from in vitro studies using testosterone as the human cytochrome P4503A substrate., Eur J Clin Pharmacol, 62, 203, 10.1007/s00228-005-0091-x
Voorman, 1998, Microsomal metabolism of delavirdine: evidence for mechanism-based inactivation of human cytochrome P450 3A., J Pharmacol Exp Ther, 287, 381
Masubuchi, 2002, Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine., Drug Metab Dispos, 30, 1143, 10.1124/dmd.30.10.1143
Masubuchi, 1999, Mechanism-based inactivation of cytochrome P450s 1A2 and 3A4 by dihydralazine in human liver microsomes., Chem Res Toxicol, 12, 1028, 10.1021/tx9901276
Yeo, 2001, Inhibitory effects of verapamil and diltiazem on simvastatin metabolism in human liver microsomes., Br J Clin Pharmacol, 51, 461, 10.1046/j.1365-2125.2001.01386.x
Ma, 2000, Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A., Drug Metab Dispos, 28, 125
Chan, 2000, Resveratrol, a red wine constituent, is a mechanism-based inactivator of cytochrome P450 3A4., Life Sci, 67, 3103, 10.1016/S0024-3205(00)00888-2
Kanamitsu, 2000, Prediction of in vivo interaction between triazolam and erythromycin based on in vitro studies using human liver microsomes and recombinant human CYP3A4., Pharmacol Res, 17, 419, 10.1023/A:1007572803027
Yamano, 2001, Prediction of midazolam-CYP3A inhibitors interaction in the human liver from in vivo/in vitro absorption, distribution, and metabolism data., Drug Metab Dispos, 29, 443
Lin, 2007, The inactivation of cytochrome P450 3A5 by 17alpha-ethynylestradiol is cytochrome b5-dependent: metabolic activation of the ethynyl moiety leads to the formation of glutathione conjugates, a heme adduct, and covalent binding to the apoprotein., J Pharmacol Exp Ther, 321, 276, 10.1124/jpet.106.117861
Hanioka, 2002, Interaction of irinotecan (CPT-11) and its active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38) with human cytochrome P450 enzymes., Drug Metab Dispos, 30, 391, 10.1124/dmd.30.4.391
Prueksaritanont, 1999, Metabolic interactions between mibefradil and HMG-CoA reductase inhibitors: an in vitro investigation with human liver preparations., Br J Clin Pharmacol, 47, 291, 10.1046/j.1365-2125.1999.00903.x
Khan, 2002, Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: an evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation., Mol Pharmacol, 61, 495, 10.1124/mol.61.3.495
Kalgutkar, 2005, Metabolic activation of the nontricyclic antidepressant trazodone to electrophilic quinone-imine and epoxide intermediates in human liver microsomes and recombinant P4503A4., Chem Biol Interact, 155, 10, 10.1016/j.cbi.2005.03.036
Kalgutkar, 2005, Bioactivation of the nontricyclic antidepressant nefazodone to a reactive quinone-imine species in human liver microsomes and recombinant cytochrome P450 3A4., Drug Metab Dispos, 33, 243, 10.1124/dmd.104.001735
Lillibridge, 1998, Characterization of the selectivity and mechanism of human cytochrome P450 inhibition by the human immunodeficiency virus-protease inhibitor nelfinavir mesylate., Drug Metab Dispos, 26, 609
Miura, 1989, Decrease in a constitutive form of cytochrome P-450 by macrolide antibiotics., J Antimicrob Chemother, 24, 551, 10.1093/jac/24.4.551
Chen, 2002, Cytochrome P450 3A4-mediated bioactivation of raloxifene: irreversible enzyme inhibition and thiol adduct formation., Chem Res Toxicol, 15, 907, 10.1021/tx0200109
Zhao, 2005, Evaluation of time-dependent inactivation of CYP3A in cryopreserved human hepatocytes., Drug Metab Dispos, 33, 853, 10.1124/dmd.104.002832
Baer, 2007, Time-dependent inactivation of P450 3A4 by raloxifene: identification of Cys239 as the site of apoprotein alkylation(1)., Chem Res Toxicol, 20, 954, 10.1021/tx700037e
Chang, 2006, The role of P-glycoprotein in the bioactivation of raloxifene., Drug Metab Dispos, 34, 2073, 10.1124/dmd.106.012179
Koudriakova, 1998, Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir., Drug Metab Dispos, 26, 552
Witkamp, 1995, The antibiotic tiamulin is a potent inducer and inhibitor of cytochrome P4503A via the formation of a stable metabolic intermediate complex. Studies in primary hepatocyte cultures and liver microsomes of the pig., Drug Metab Dispos, 23, 542
Obach, 2007, Mechanism-based inactivation of human cytochrome p450 enzymes and the prediction of drug-drug interactions., Drug Metab Dispos, 35, 246, 10.1124/dmd.106.012633
Perloff, 2005, Atazanavir: effects on P-glycoprotein transport and CYP3A metabolism in vitro., Drug Metab Dispos, 33, 764, 10.1124/dmd.104.002931
Luo, 2003, Concurrent induction and mechanism-based inactivation of CYP3A4 by an L-valinamide derivative., Drug Metab Dispos, 31, 1170, 10.1124/dmd.31.9.1170
Chiba, 1995, Potent and selective inactivation of human liver microsomal cytochrome P-450 isoforms by L-754,394, an investigational human immune deficiency virus protease inhibitor., J Pharmacol Exp Ther, 275, 1527
Lightning, 2000, Mechanism-based inactivation of cytochrome P450 3A4 by L-754,394., Biochemistry, 39, 4276, 10.1021/bi992412u
Bateman, 2004, Detection of covalent adducts to cytochrome P450 3A4 using liquid chromatography mass spectrometry., Chem Res Toxicol, 17, 1356, 10.1021/tx0498861
Wang, 2005, Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil., Drug Metab Dispos, 33, 664, 10.1124/dmd.104.001834
Chatterjee, 2003, Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components., Drug Metab Dispos, 31, 1391, 10.1124/dmd.31.11.1391
Alvarez-Diez, 2004, Mechanism-based inactivation of cytochrome P450 3A4 by 4-ipomeanol., Chem Res Toxicol, 17, 150, 10.1021/tx034143l
Schmiedlin-Ren, 1997, Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins., Drug Metab Dispos, 25, 1228
He, 1998, Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice., Chem Res Toxicol, 11, 252, 10.1021/tx970192k
Eagling, 1999, Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components., Br J Clin Pharmacol, 48, 543, 10.1046/j.1365-2125.1999.00052.x
Kent, 2002, The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9., Drug Metab Dispos, 30, 709, 10.1124/dmd.30.6.709
Iwata, 2004, Identification and characterization of potent CYP3A4 inhibitors in Schisandra fruit extract., Drug Metab Dispos, 32, 1351, 10.1124/dmd.104.000646
Iwata, 2005, Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract., Drug Metab Pharmacokinet, 20, 34, 10.2133/dmpk.20.34
Stupans, 2001, Inactivation of cytochrome P450 by the food-derived complex phenol oleuropein., Food Chem Toxicol, 39, 1119, 10.1016/S0278-6915(01)00060-6
Stresser, 2004, Highly selective inhibition of human CYP3Aa in vitro by azamulin and evidence that inhibition is irreversible., Drug Metab Dispos, 32, 105, 10.1124/dmd.32.1.105
Butler, 1997, Biotransformation of parathion in human liver: participation of CYP3A4 and its inactivation during microsomal parathion oxidation., J Pharmacol Exp Ther, 280, 966
Jacobsen, 2000, In vitro evaluation of the disposition of A novel cysteine protease inhibitor., Drug Metab Dispos, 28, 1343
Zdravkovic, 2003, A clinical study investigating the pharmacokinetic interaction between NN703 (tabimorelin), a potential inhibitor of CYP3A4 activity, and midazolam, a CYP3A4 substrate., Eur J Clin Pharmacol, 58, 683, 10.1007/s00228-002-0539-1
Ring, 2005, Effect of tadalafil on cytochrome P450 3A4-mediated clearance: studies in vitro and in vivo., Clin Pharmacol Ther, 77, 63, 10.1016/j.clpt.2004.09.006
Booker, 2002, Pharmacokinetic and pharmacodynamic interactions between diltiazem and methylprednisolone in healthy volunteers., Clin Pharmacol Ther, 72, 370, 10.1067/mcp.2002.127944