Inhibition of CYP2C19 and CYP3A4 by omeprazole metabolites and their contribution to drug-drug interactionss

Drug Metabolism and Disposition

Volumn 41, Issue 7, 2013, Pages 1414-1424

  Shirasaka, Yoshiyuki ^a,c   Sager, Jennifer E ^a   Lutz, Justin D ^a   Davis, Connie ^b   Isoherranen, Nina ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b Seattle Children's Hospital   (United States)

^c KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYOMEPRAZOLE; 5' O NOROMEPRAZOLE; CAFFEINE; CARBOXYOMEPRAZOLE; CYTOCHROME P450 2C19; CYTOCHROME P450 3A4; DEXTROMETHORPHAN; DRUG METABOLITE; MIDAZOLAM; OMEPRAZOLE; OMEPRAZOLE SULFONE; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; ARTICLE; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG COMPETITION; DRUG ELIMINATION; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MALE; NORMAL HUMAN; PREDICTION; PRIORITY JOURNAL; RISK ASSESSMENT; SINGLE DRUG DOSE;

ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 CYP3A; DRUG INTERACTIONS; ENZYME INHIBITORS; HUMANS; OMEPRAZOLE;

EID: 84879068823     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.051722     Document Type: Article

References (32)

1. Andersson T, Miners JO, VeroneseME, and Birkett DJ (1994) Identification of human liver cytochrome P450 isoforms mediating secondary omeprazole metabolism. Br J Clin Pharmacol 37:597-604.
2. Andersson T and Weidolf L (2008) Stereoselective disposition of proton pump inhibitors. Clin Drug Investig 28:263-279.
3. Angiolillo DJ, Gibson CM, Cheng S, Ollier C, Nicolas O, Bergougnan L, Perrin L, LaCreta FP, Hurbin F, and Dubar M (2011) Differential effects of omeprazole and pantoprazole on the pharmacodynamics and pharmacokinetics of clopidogrel in healthy subjects: Randomized, placebo-controlled, crossover comparison studies. Clin Pharmacol Ther 89:65-74.
4. Berry LM and Zhao Z (2008) An examination of IC50 and IC50-shift experiments in assessing time-dependent inhibition of CYP3A4, CYP2D6 and CYP2C9 in human liver microsomes. Drug Metab Lett 2:51-59.
5. Boulenc X, Djebli N, Shi J, Perrin L, Brian W, Van Horn R, and Hurbin F (2012) Effects of omeprazole and genetic polymorphism of CYP2C19 on the clopidogrel active metabolite. Drug Metab Dispos 40:187-197.
6. Dixit RK, Chawla AB, Kumar N, and Garg SK (2001) Effect of omeprazole on the pharmacokinetics of sustained-release carbamazepine in healthy male volunteers. Methods Find Exp Clin Pharmacol 23:37-39.
7. Fahmi OA, Boldt S, Kish M, Obach RS, and Tremaine LM (2008) Prediction of drug-drug interactions from in vitro induction data: Application of the relative induction score approach using cryopreserved human hepatocytes. Drug Metab Dispos 36:1971-1974.
8. Fujioka Y, Kunze KL, and Isoherranen N (2012) Risk assessment of mechanism-based inactivation in drug-drug interactions. Drug Metab Dispos 40:1653-1657.
9. Funck-Brentano C, Becquemont L, Lenevu A, Roux A, Jaillon P, and Beaune P (1997) Inhibition by omeprazole of proguanil metabolism: Mechanism of the interaction in vitro and prediction of in vivo results from the in vitro experiments. J Pharmacol Exp Ther 280:730-738.
10. Grimm SW, Einolf HJ, Hall SD, He K, Lim H-K, Ling KH, Lu C, Nomeir AA, Seibert E, and 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.
11. Ishizaki T, Chiba K, Manabe K, Koyama E, Hayashi M, Yasuda S, Horai Y, Tomono Y, Yamato C, and Toyoki T (1995) Comparison of the interaction potential of a new proton pump inhibitor, E3810, versus omeprazole with diazepam in extensive and poor metabolizers of Smephenytoin 49-hydroxylation. Clin Pharmacol Ther 58:155-164.
12. Isoherranen N, Hachad H, Yeung CK, and Levy RH (2009) Qualitative analysis of the role of metabolites in inhibitory drug-drug interactions: Literature evaluation based on the metabolism and transport drug interaction database. Chem Res Toxicol 22:294-298.
13. Li XQ, Andersson TB, Ahlström M, and Weidolf L (2004) Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos 32:821-827.
14. Lutz JD and Isoherranen N (2012) Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: Dextromethorphan and omeprazole. Drug Metab Dispos 40: 159-168.
15. Nishiya Y, Hagihara K, Kurihara A, Okudaira N, Farid NA, Okazaki O, and Ikeda T (2009) Comparison of mechanism-based inhibition of human cytochrome P450 2C19 by ticlopidine, clopidogrel, and prasugrel. Xenobiotica 39:836-843.
16. 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.
17. Ogilvie BW, Yerino P, Kazmi F, Buckley DB, Rostami-Hodjegan A, Paris BL, Toren P, and Parkinson A (2011) The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: Implications for coadministration with clopidogrel. Drug Metab Dispos 39:2020-2033.
18. Reese MJ, Wurm RM, Muir KT, Generaux GT, St John-Williams L, and McConn DJ (2008) An in vitro mechanistic study to elucidate the desipramine/bupropion clinical drug-drug interaction. Drug Metab Dispos 36:1198-1201.
19. Regårdh CG, Andersson T, Lagerström PO, Lundborg P, and Skånberg I (1990) The pharmacokinetics of omeprazole in humans-a study of single intravenous and oral doses. Ther Drug Monit 12:163-172.
20. Rowland Yeo K, Jamei M, Yang J, Tucker GT, and Rostami-Hodjegan A (2010) Physiologically based mechanistic modelling to predict complex drug-drug interactions involving simultaneous competitive and time-dependent enzyme inhibition by parent compound and its metabolite in both liver and gut-the effect of diltiazem on the time-course of exposure to triazolam. Eur J Pharm Sci 39:298-309.
21. Ryu JY, Song IS, Sunwoo YE, Shon JH, Liu KH, Cha IJ, and Shin JG (2007) Development of the "Inje cocktail" for high-throughput evaluation of five human cytochrome P450 isoforms in vivo. Clin Pharmacol Ther 82:531-540.
22. Soons PA, van den Berg G, Danhof M, van Brummelen P, Jansen JB, Lamers CB, and Breimer DD (1992) Influence of single-and multiple-dose omeprazole treatment on nifedipine pharmacokinetics and effects in healthy subjects. Eur J Clin Pharmacol 42:319-324.
23. Templeton IE, Thummel KE, Kharasch ED, Kunze KL, Hoffer C, Nelson WL, and Isoherranen N (2008) Contribution of itraconazole metabolites to inhibition of CYP3A4 in vivo. Clin Pharmacol Ther 83:77-85.
24. VandenBrink BM and Isoherranen N (2010) The role of metabolites in predicting drug-drug interactions: Focus on irreversible cytochrome P450 inhibition. Curr Opin Drug Discov Devel 13:66-77.
25. Waley SG (1985) Kinetics of suicide substrates. Practical procedures for determining parameters. Biochem J 227:843-849.
26. Yamaoka K, Tanigawara T, Nakagawa T, and Uno T (1981) A pharmacokinetic analysis program (MULTI) for microcomputer. J Pharmacobiodyn 4:879-885.
27. Yeung CK, Fujioka Y, Hachad H, Levy RH, and Isoherranen N (2011) Are circulating metabolites important in drug-drug interactions?: Quantitative analysis of risk prediction and inhibitory potency. Clin Pharmacol Ther 89:105-113.
28. Yu H and Tweedie D (2013) A perspective on the contribution of metabolites to drug-drug interaction potential: The need to consider both circulating levels and inhibition potency. Drug Metab Dispos 41:536-540.
29. Yu KS, Yim DS, Cho JY, Park SS, Park JY, Lee KH, Jang IJ, Yi SY, Bae KS, and Shin SG (2001) Effect of omeprazole on the pharmacokinetics of moclobemide according to the genetic polymorphism of CYP2C19. Clin Pharmacol Ther 69:266-273.
30. Zhang X, Jones DR, and Hall SD (2009a) Prediction of the effect of erythromycin, diltiazem, and their metabolites, alone and in combination, on CYP3A4 inhibition. Drug Metab Dispos 37: 150-160.
31. Zhang X, Quinney SK, Gorski JC, Jones DR, and Hall SD (2009b) Semiphysiologically based pharmacokinetic models for the inhibition of midazolam clearance by diltiazem and its major metabolite. Drug Metab Dispos 37:1587-1597.
32. Zvyaga T, Chang SY, Chen C, Yang Z, Vuppugalla R, Hurley J, Thorndike D, Wagner A, Chimalakonda A, and Rodrigues AD (2012) Evaluation of six proton pump inhibitors as inhibitors of various human cytochromes P450: Focus on cytochrome P450 2C19. Drug Metab Dispos 40:1698-1711.