Prediction of human drug-drug interactions from time-dependent inactivation of CYP3A4 in primary hepatocytes using a population-based simulator

Drug Metabolism and Disposition

Volumn 37, Issue 12, 2009, Pages 2330-2339

  Xu, Lilly ^a   Chen, Yuping ^a   Pan, Yvonne ^a   Skiles, Gary L ^a   Shou, Magang ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLARITHROMYCIN; CYTOCHROME P450 3A4; DILTIAZEM; ERYTHROMYCIN; TROLEANDOMYCIN; VERAPAMIL;

ARTICLE; DRUG CLEARANCE; DRUG DISPOSITION; DRUG DISTRIBUTION; DRUG INHIBITION; DRUG METABOLISM; DRUG POTENTIATION; HUMAN; HUMAN CELL; LIVER CELL; LIVER MICROSOME; PREDICTION; PRIORITY JOURNAL; SIMULATION;

ADULT; AGED, 80 AND OVER; CELLS, CULTURED; COMPUTER SIMULATION; CYTOCHROME P-450 CYP3A; DRUG INTERACTIONS; ENZYME INHIBITORS; FEMALE; HEPATOCYTES; HUMANS; HYDROXYLATION; KINETICS; MALE; MICROSOMES, LIVER; MIDAZOLAM; MIDDLE AGED; MODELS, BIOLOGICAL; REPRODUCIBILITY OF RESULTS; YOUNG ADULT;

EID: 71049127036     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.025494     Document Type: Article

References (66)

1. Abernethy DR, Kaminsky LS, and Dickinson TH (1991) Selective inhibition of warfarin metabolism by diltiazem in humans. J Pharmacol Exp Ther 257:411-415.
2. Atkinson A, Kenny JR, and Grime K (2005) Automated assessment of time-dependent inhibition of human cytochrome P450 enzymes using liquid chromatography-tandem mass spectrometry analysis. Drug Metab Dispos 33:1637-1647. (Pubitemid 41539961)
3. Austin RP, Barton P, Mohmed S, and Riley RJ (2005) The binding of drugs to hepatocytes and its relationship to physicochemical properties. Drug Metab Dispos 33:419-425. (Pubitemid 40279943)
4. Backman JT, Olkkola KT, Aranko K, Himberg JJ, and Neuvonen PJ (1994) Dose of midazolam should be reduced during diltiazem and verapamil treatments. Br J Clin Pharmacol 37:221-225. (Pubitemid 24212179)
5. Bauer LA, Horn JR, Maxon MS, Easterling TR, Shen DD, and Strandness DE Jr (2000) Effect of metoprolol and verapamil administered separately and concurrently after single doses on liver blood flow and drug disposition. J Clin Pharmacol 40:533-543.
6. Calabresi L, Pazzucconi F, Ferrara S, Di Paolo A, Tacca MD, and Sirtori C (2004) Pharmacokinetic interactions between omeprazole/pantoprazole and clarithromycin in health volunteers. Pharmacol Res 49:493-499. (Pubitemid 38283871)
7. Crivellato E, Candussio L, Rosati AM, Bartoli-Klugmann F, Mallardi F, and Decorti G (2002) The fluorescent probe Bodipy-FL-verapamil is a substrate for both P-glycoprotein and multidrug resistance-related protein (MRP)-1. J Histochem Cytochem 50:731-734. (Pubitemid 34437566)
8. Einolf HJ (2007) Comparison of different approaches to predict metabolic drug-drug interactions. Xenobiotica 37:1257-1294.
9. Foti RS and Wahlstrom JL (2008) CYP2C19 inhibition: the impact of substrate probe selection on in vitro inhibition profiles. Drug Metab Dispos 36:523-528.
10. Freeman DJ, Martell R, Carruthers SG, Heinrichs D, Keown PA, and Stiller CR (1987) Cyclosporin-erythromycin interaction in normal subjects. Br J Clin Pharmacol 23:776-778.
11. Furuta T, Ohashi K, Kobayashi K, Iida I, Yoshida H, Shirai N, Takashima M, Kosuge K, Hanai H, Chiba K, et al. (1999) Effects of clarithromycin on the metabolism of omeprazole in relation to CYP2C19 genotype status in humans. Clin Pharmacol Ther 66:265-274. (Pubitemid 29451758)
12. Genazzani E (1975) The pharmacological and pharmacokinetic properties of troleandomycin. Quad Antibiot 35-56.
13. 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.
14. Gomez DY, Wacher VJ, Tomlanovich SJ, Hebert MF, and Benet LZ (1995) The effects of ketoconazole on the intestinal metabolism and bioavailability of cyclosporine. Clin Pharmacol Ther 58:15-19.
15. Greenblatt DJ, von Moltke LL, Harmatz JS, Counihan M, Graf JA, Durol AL, Mertzanis P, Duan SX, Wright CE, and Shader RI (1998a) Inhibition of triazolam clearance by macrolide antimicrobial agents: in vitro correlates and dynamic consequences. Clin Pharmacol Ther 64:278-285. (Pubitemid 28462288)
16. Greenblatt DJ, Wright CE, von Moltke LL, Harmatz JS, Ehrenberg BL, Harrel LM, Corbett K, Counihan M, Tobias S, and Shader RI (1998b) Ketoconazole inhibition of triazolam and alprazolam clearance: differential kinetic and dynamic consequences. Clin Pharmacol Ther 64:237-247. (Pubitemid 28462284)
17. Guengerich FP (2003) Cytochromes P450, drugs, and diseases. Mol Interv 3:194-204.
18. Gupta SK, Bakran A, Johnson RW, and Rowland M (1988) Erythromycin enhances the absorption of cyclosporin. Br J Clin Pharmacol 25:401-402.
19. Gurley B, Hubbard MA, Williams DK, Thaden J, Tong Y, Gentry WB, Breen P, Carrier DJ, and Cheboyina S (2006) Assessing the clinical significance of botanical supplementation on human cytochrome P450 3A activity: comparison of a milk thistle and black cohosh product to rifampin and clarithromycin. J Clin Pharmacol 46:201-213. (Pubitemid 43149297)
20. Gustavson LE, Kaiser JF, Edmonds AL, Locke CS, DeBartolo ML, and Schneck DW (1995) Effect of omeprazole on concentrations of clarithromycin in plasma and gastric tissue at steady state. Antimicrob Agents Chemother 39:2078-2083.
21. He N, Huang SL, Zhu RH, Tan ZR, Liu J, Zhu B, and Zhou HH (2003) Inhibitory effect of troleandomycin on the metabolism of omeprazole is CYP2C19 genotype-dependent. Xenobiotica 33:211-221. (Pubitemid 36237942)
22. Hedaya MA, El-Afify DR, and El-Maghraby GM (2006) The effect of ciprofloxacin and clarithromycin on sildenafil oral bioavailability in human volunteers. Biopharm Drug Dispos 27:103-110.
23. Hermann DJ, Krol TF, Dukes GE, Hussey EK, Danis M, Han YH, Powell JR, and Hak LJ (1992) Comparison of verapamil, diltiazem, and labetalol on the bioavailability and metabolism of imipramine. J Clin Pharmacol 32:176-183.
24. Ito K, Iwatsubo T, Kanamitsu S, Ueda K, Suzuki H, and Sugiyama Y (1998) Prediction of pharmacokinetic alterations caused by drug-drug interactions: metabolic interaction in the liver. Pharmacol Rev 50:387-412. (Pubitemid 28477680)
25. Ito K, Ogihara K, Kanamitsu S, and Itoh T (2003) Prediction of the in vivo interaction between midazolam and macrolides based on in vitro studies using human liver microsomes. Drug Metab Dispos 31:945-954. (Pubitemid 36759066)
26. Jacobson TA (2004) Comparative pharmacokinetic interaction profiles of pravastatin, simvastatin, and atorvastatin when coadministered with cytochrome P450 inhibitors. Am J Cardiol 94:1140-1146.
27. Jayasagar G, Dixit AA, Kishan V, and Rao YM (2000) Effect of clarithromycin on the pharmacokinetics of tolbutamide. Drug Metabol Drug Interact 16:207-215.
28. Kantola T, Kivistö KT, and Neuvonen PJ (1998) Erythromycin and verapamil considerably increase serum simvastatin and simvastatin acid concentrations. Clin Pharmacol Ther 64:177-182. (Pubitemid 28423853)
29. Kharasch ED, Hoffer C, Whittington D, and Sheffels P (2004) Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadone. Clin Pharmacol Ther 76:250-269. (Pubitemid 39221799)
30. Kim M, Shen DD, Eddy AC, Nelson WL, and Roskos LK (1993) Inhibition of the enantioselective oxidative metabolism of metoprolol by verapamil in human liver microsomes. Drug Metab Dispos 21:309-317. (Pubitemid 23120106)
31. Matic S, Geisler DA, Møller IM, Widell S, and Rasmusson AG (2005) Alamethicin permeabilizes the plasma membrane and mitochondria but not the tonoplast in tobacco (Nicotiana tabacum L. cv Bright Yellow) suspension cells. Biochem J 389:695-704. (Pubitemid 41117329)
32. Mayhew BS, Jones DR, and Hall SD (2000) An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab Dispos 28:1031-1037.
33. McConn DJ 2nd, Lin YS, Allen K, Kunze KL, and Thummel KE (2004) Differences in the inhibition of cytochromes P450 3A4 and 3A5 by metabolite-inhibitor complex-forming drugs. Drug Metab Dispos 32:1083-1091.
34. McLean AJ, Knight R, Harrison PM, and Harper RW (1985) Clearance-based oral drug interaction between verapamil and metoprolol and comparison with atenolol. Am J Cardiol 55:1628-1629. (Pubitemid 15059300)
35. Muirhead GJ, Faulkner S, Harness JA, and Taubel J (2002) The effects of steady-state erythromycin and azithromycin on the pharmacokinetics of sildenafil in healthy volunteers. Br J Clin Pharmacol 53 (Suppl 1):37S-43S. (Pubitemid 41712964)
36. Murdoch DL, Thomson GD, Thompson GG, Murray GD, Brodie MJ, and McInnes GT (1991) Evaluation of potential pharmacodynamic and pharmacokinetic interactions between verapamil and propranolol in normal subjects. Br J Clin Pharmacol 31:323-332.
37. Obach RS, Walsky RL, and Venkatakrishnan K (2007) Mechanism-based inactivation of human cytochrome P450 enzymes and the prediction of drug-drug interactions. Drug Metab Dispos 35:246-255. (Pubitemid 46148737)
38. Obach RS, Walsky RL, Venkatakrishnan K, Houston JB, and Tremaine LM (2005) 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 78:582-592. (Pubitemid 41773634)
39. Olkkola KT, Aranko K, Luurila H, Hiller A, Saarnivaara L, Himberg JJ, and Neuvonen PJ (1993) A potentially hazardous interaction between erythromycin and midazolam. Clin Pharmacol Ther 53:298-305. (Pubitemid 23094372)
40. Phillips JP, Antal EJ, and Smith RB (1986) A pharmacokinetic drug interaction between erythromycin and triazolam. J Clin Psychopharmacol 6:297-299.
41. Phimmasone S and Kharasch ED (2001) A pilot evaluation of alfentanil-induced miosis as a noninvasive probe for hepatic cytochrome P450 3A4 (CYP3A4) activity in humans. Clin Pharmacol Ther 70:505-517. (Pubitemid 34008407)
42. Polasek TM, Elliot DJ, Lewis BC, and Miners JO (2004) Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther 311:996-1007.
43. Rodrigues AD (1999) Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochem Pharmacol 57:465-480.
44. Rodrigues AD, Roberts EM, Mulford DJ, Yao Y, and Ouellet D (1997) Oxidative metabolism of clarithromycin in the presence of human liver microsomes. Major role for the cytochrome P4503A (CYP3A) subfamily. Drug Metab Dispos 25:623-630. (Pubitemid 27213105)
45. Rodvold KA (1999) Clinical pharmacokinetics of clarithromycin. Clin Pharmacokinet 37:385-398.
46. Rostami-Hodjegan A and Tucker GT (2007) Simulation and prediction of in vivo drug metabolism in human populations from in vitro data. Nat Rev Drug Discov 6:140-148. (Pubitemid 46745341)
47. Saeki T, Ueda K, Tanigawara Y, Hori R, and Komano T (1993) P-glycoprotein-mediated transcellular transport of MDR-reversing agents. FEBS Lett 324:99-102. (Pubitemid 23165045)
48. Sirmans SM, Pieper JA, Lalonde RL, Smith DG, and Self TH (1988) Effect of calcium channel blockers on theophylline disposition. Clin Pharmacol Ther 44:29-34. (Pubitemid 18191285)
49. Sketris IS, Wright MR, and West ML (1996) Possible role of the intestinal P-450 enzyme system in a cyclosporine-clarithromycin interaction. Pharmacotherapy 16:301-305. (Pubitemid 26087940)
50. Sutton D, Butler AM, Nadin L, and Murray M (1997) Role of CYP3A4 in human hepatic diltiazem N-demethylation: inhibition of CYP3A4 activity by oxidized diltiazem metabolites. J Pharmacol Exp Ther 282:294-300. (Pubitemid 27425554)
51. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, and Murakami T (1998) Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol 358:289-294. (Pubitemid 28498189)
52. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, and Wilkinson GR (1996) Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 59:491-502. (Pubitemid 26193889)
53. Tracy TS, Korzekwa KR, Gonzalez FJ, and Wainer IW (1999) Cytochrome P450 isoforms involved in metabolism of the enantiomers of verapamil and norverapamil. Br J Clin Pharmacol 47:545-552. (Pubitemid 29199727)
54. von Moltke LL, Greenblatt DJ, Schmider J, Wright CE, Harmatz JS, and Shader RI (1998) In vitro approaches to predicting drug interactions in vivo. Biochem Pharmacol 55:113-122. (Pubitemid 28006177)
55. Wadhwa NK, Schroeder TJ, O'Flaherty E, Pesce AJ, Myre SA, Munda R, and First MR (1987) Interaction between erythromycin and cyclosporine in a kidney and pancreas allograft recipient. Ther Drug Monit 9:123-125. (Pubitemid 17028036)
56. Wang JS, Wang W, Xie HG, Huang SL, and Zhou HH (1997a) Effect of troleandomycin on the pharmacokinetics of imipramine in Chinese: the role of CYP3A. Br J Clin Pharmacol 44:195-198. (Pubitemid 27327077)
57. Wang RW, Newton DJ, Scheri TD, and Lu AY (1997b) Human cytochrome P450 3A4-catalyzed testosterone 6β-hydroxylation and erythromycin N-demethylation. Competition during catalysis. Drug Metab Dispos 25:502-507.
58. Warot D, Bergougnan L, Lamiable D, Berlin I, Bensimon G, Danjou P, and Puech AJ (1987) Troleandomycin-triazolam interaction in healthy volunteers: pharmacokinetic and psychometric evaluation. Eur J Clin Pharmacol 32:389-393. (Pubitemid 17077187)
59. Wester MR, Lasker JM, Johnson EF, and Raucy JL (2000) CYP2C19 participates in tolbutamide hydroxylation by human liver microsomes. Drug Metab Dispos 28:354-359.
60. Yang J, Jamei M, Heydari A, Yeo KR, de la Torre R, Farré M, Tucker GT, and Rostami-Hodjegan A (2006) Implications of mechanism-based inhibition of CYP2D6 for the pharmacokinetics and toxicity of MDMA. J Psychopharmacol 20:842-849. (Pubitemid 44622750)
61. Yang J, Jamei M, Yeo KR, Tucker GT, and Rostami-Hodjegan A (2007) Prediction of intestinal first-pass drug metabolism. Curr Drug Metab 8:676-684. (Pubitemid 47578116)
62. Yang J, Liao M, Shou M, Jamei M, Yeo KR, Tucker GT, and Rostami-Hodjegan A (2008) Cytochrome p450 turnover: regulation of synthesis and degradation, methods for determining rates, and implications for the prediction of drug interactions. Curr Drug Metab 9:384-394. (Pubitemid 352025193)
63. Yasui N, Otani K, Kaneko S, Ohkubo T, Osanai T, Sugawara K, Chiba K, and Ishizaki T (1996) A kinetic and dynamic study of oral alprazolam with and without erythromycin in humans: in vivo evidence for the involvement of CYP3A4 in alprazolam metabolism. Clin Pharmacol Ther 59:514-519. (Pubitemid 26193890)
64. Yeates RA, Laufen H, and Zimmermann T (1996) Interaction between midazolam and clarithromycin: comparison with azithromycin. Int J Clin Pharmacol Ther 34:400-405. (Pubitemid 26305815)
65. Yeo KR and Yeo WW (2001) Inhibitory effects of verapamil and diltiazem on simvastatin metabolism in human liver microsomes. Br J Clin Pharmacol 51:461-470. (Pubitemid 32852984)
66. Zimmermann T, Yeates RA, Laufen H, Scharpf F, Leitold M, and Wildfeuer A (1996) Influence of the antibiotics erythromycin and azithromycin on the pharmacokinetics and pharmacodynamics of midazolam. Arzneimittelforschung 46:213-217. (Pubitemid 26080111)