Investigating the contribution of CYP2J2 to ritonavir metabolism in vitro and in vivo

Biochemical Pharmacology

Volumn 91, Issue 1, 2014, Pages 109-118

  Kaspera, Rüdiger ^a,c   Kirby, Brian J ^a,d   Sahele, Tariku ^a   Collier, Ann C ^a   Kharasch, Evan D ^b   Unadkat, Jashvant D ^a   Totah, Rheem A ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b WASHINGTON UNIVERSITY   (United States)

^c ASTRAZENECA   (United Kingdom)

^d GILEAD SCIENCES   (United States)

Author keywords

CYP2D6; CYP2J2; CYP3A4; In vivo; Ritonavir; Simcyp; Time dependent inhibition

Indexed keywords

CYTOCHROME P450 2D6; CYTOCHROME P450 2J2; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; RITONAVIR;

AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISPOSITION; DRUG DOSE ESCALATION; DRUG METABOLISM; ENZYME ACTIVITY; GENOTYPE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER CLEARANCE; LIVER MICROSOME; MAXIMUM PLASMA CONCENTRATION; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; PROTEIN FUNCTION;

CYP2D6; CYP2J2; CYP3A4; IN VIVO; RITONAVIR; SIMCYP; TIME DEPENDENT INHIBITION;

CYTOCHROME P-450 ENZYME SYSTEM; DEXTROMETHORPHAN; HUMANS; METABOLIC DETOXICATION, DRUG; MICROSOMES, LIVER; MODELS, BIOLOGICAL; RITONAVIR;

EID: 84905444396     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2014.06.020     Document Type: Article

References (36)

1. M.A. Thompson, J.A. Aberg, J.F. Hoy, A. Telenti, C. Benson, and P. Cahn et al. Antiretroviral treatment of adult HIV infection: 2012 recommendations of the International Antiviral Society-USA panel JAMA 308 2012 387 402
2. A.A. Mathias, S. West, J. Hui, and B.P. Kearney Dose-response of ritonavir on hepatic CYP3A activity and elvitegravir oral exposure Clin Pharmacol Ther 85 2009 64 70
3. R.K. Zeldin, and R.A. Petruschke Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients J Antimicrob Chemother 53 2004 4 9 (Pubitemid 38072176)
4. E. Gangl, I. Utkin, N. Gerber, and P. Vouros Structural elucidation of metabolites of ritonavir and indinavir by liquid chromatography-mass spectrometry J Chromatogr A 974 2002 91 101
5. A. Hsu, G.R. Granneman, G. Witt, C. Locke, J. Denissen, and A. Molla et al. Multiple-dose pharmacokinetics of ritonavir in human immunodeficiency virus-infected subjects Antimicrob Agents Chemother 41 1997 898 905 (Pubitemid 27194157)
6. T. Koudriakova, E. Iatsimirskaia, I. Utkin, E. Gangl, P. Vouros, and E. Storozhuk et al. 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 1998 552 561 (Pubitemid 28498361)
7. G.N. Kumar, J. Dykstra, E.M. Roberts, V.K. Jayanti, D. Hickman, and J. Uchic et al. Potent inhibition of the cytochrome P-450 3A-mediated human liver microsomal metabolism of a novel HIV protease inhibitor by ritonavir: a positive drug-drug interaction Drug Metab Dispos 27 1999 902 908 (Pubitemid 29347590)
8. M.G. Soars, K. Grime, and R.J. Riley Comparative analysis of substrate and inhibitor interactions with CYP3A4 and CYP3A5 Xenobiotica 36 2006 287 299
9. B.J. Kirby, A.C. Collier, E.D. Kharasch, D. Whittington, K.E. Thummel, and J.D. Unadkat Complex drug interactions of HIV protease inhibitors 1: inactivation, induction, and inhibition of cytochrome P450 3A by ritonavir or nelfinavir Drug Metab Dispos 39 2011 1070 1078
10. B.J. Kirby, A.C. Collier, E.D. Kharasch, V. Dixit, P. Desai, and D. Whittington et al. Complex drug interactions of HIV protease inhibitors 2: in vivo induction and in vitro to in vivo correlation of induction of cytochrome P450 1A2, 2B6, and 2C9 by ritonavir or nelfinavir Drug Metab Dispos 39 2011 2329 2337
11. B.J. Kirby, A.C. Collier, E.D. Kharasch, D. Whittington, K.E. Thummel, and J.D. Unadkat Complex drug interactions of the HIV protease inhibitors 3: effect of simultaneous or staggered dosing of digoxin and ritonavir, nelfinavir, rifampin, or bupropion Drug Metab Dispos 40 2012 610 616
12. M. Ingelman-Sundberg Genetic polymorphisms of cytochrome P450 2D6 (CYP2D6): clinical consequences, evolutionary aspects and functional diversity Pharmacogenomics J 5 2005 6 13 (Pubitemid 40220611)
13. I. Fleming Vascular cytochrome p450 enzymes: physiology and pathophysiology Trends Cardiovascul Med 18 2008 20 25
14. T. Hashizume, S. Imaoka, M. Mise, Y. Terauchi, T. Fujii, and H. Miyazaki et al. Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes J Pharmacol Exp Ther 300 2002 298 304 (Pubitemid 34028540)
15. P. Lafite, S. Dijols, D.C. Zeldin, P.M. Dansette, and D. Mansuy Selective, competitive and mechanism-based inhibitors of human cytochrome P450 2J2 Arch Biochem Biophys 464 2007 155 168 (Pubitemid 47210920)
16. K.H. Liu, M.G. Kim, D.J. Lee, Y.J. Yoon, M.J. Kim, and J.H. Shon et al. Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A Drug Metab Dispos 34 2006 1793 1797
17. S. Matsumoto, T. Hirama, T. Matsubara, K. Nagata, and Y. Yamazoe Involvement of CYP2J2 on the intestinal first-pass metabolism of antihistamine drug, astemizole Drug Metab Dispos 30 2002 1240 1245 (Pubitemid 35265831)
18. S. Matsumoto, and Y. Yamazoe Involvement of multiple human cytochromes P450 in the liver microsomal metabolism of astemizole and a comparison with terfenadine Br J Clin Pharmacol 51 2001 133 142 (Pubitemid 32216061)
19. C.A. Lee, D. Neul, A. Clouser-Roche, D. Dalvie, M.R. Wester, and Y. Jiang et al. Identification of novel substrates for human cytochrome P450 2J2 Drug Metab Dispos 38 2010 347 356
20. M. Xu, W. Ju, H. Hao, and G. Wang Li P. Cytochrome P450 2J2: distribution, function, regulation, genetic polymorphisms and clinical significance Drug Metab Rev 45 2013 311 352
21. M.F. Paine, M. Khalighi, J.M. Fisher, D.D. Shen, K.L. Kunze, and C.L. Marsh et al. Characterization of interintestinal and intraintestinal variations in human CYP3A-dependent metabolism J Pharmacol Exp Ther 283 1997 1552 1562 (Pubitemid 28016533)
22. Y.S. Lin, A.L. Dowling, S.D. Quigley, F.M. Farin, J. Zhang, and J. Lamba et al. Co-regulation of CYP3A4 and CYP3A5 and contribution to hepatic and intestinal midazolam metabolism Mol Pharmacol 62 2002 162 172 (Pubitemid 34680528)
23. C.A. Lee, J.P. Jones III, J. Katayama, R. Kaspera, Y. Jiang, and S. Freiwald et al. Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity Drug Metab Dispos 40 2012 943 951
24. R.S. Obach, and A.E. Reed-Hagen Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach Drug Metab Dispos 30 2002 831 837 (Pubitemid 34671096)
25. J. Barre, J.M. Chamouard, G. Houin, and J.P. Tillement Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid Clin Chem 31 1985 60 64 (Pubitemid 15079346)
26. Y. Yang, M.F. Grubb, C.E. Luk, W.G. Humphreys, and J.L. Josephs Quantitative estimation of circulating metabolites without synthetic standards by ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry in combination with UV correction Rapid Commun Mass Spectrom 25 2011 3245 3251
27. L. Brunton, B. Chabner, and B. Knollman Goodman and Gilman's the pharmacological basis of therapeutics 2010 McGraw-Hill Professional New York
28. C.S. Ernest 2nd, S.D. Hall, and D.R. Jones Mechanism-based inactivation of CYP3A by HIV protease inhibitors J Pharmacol Exp Ther 312 2005 583 591 (Pubitemid 40189555)
29. J.F. Denissen, B.A. Grabowski, M.K. Johnson, A.M. Buko, D.J. Kempf, and S.B. Thomas et al. Metabolism and disposition of the HIV-1 protease inhibitor ritonavir (ABT-538) in rats, dogs, and humans Drug Metab Dispos 25 1997 489 501 (Pubitemid 27209374)
30. E.G. Hrycay, and S.M. Bandiera Cytochrome P454 enzymes S.C. Gad, Preclinical development handbook: ADME and biopharmaceutical properties 2008 Wiley & Sons New York
31. M. Ingelman-Sundberg, S.C. Sim, A. Gomez, and C. Rodriguez-Antona Influence of cytochrome P450 polymorphisms on drug therapies: pharmacogenetic, pharmacoepigenetic and clinical aspects Pharmacol Ther 116 2007 496 526 (Pubitemid 350116943)
32. W.F. Bierman, G.L. Scheffer, A. Schoonderwoerd, G. Jansen, M.A. van Agtmael, and S.A. Danner et al. Protease inhibitors atazanavir, lopinavir and ritonavir are potent blockers, but poor substrates, of ABC transporters in a broad panel of ABC transporter-overexpressing cell lines J Antimicrob Chemother 65 2010 1672 1680
33. E.D. Kharasch, P.S. Bedynek, S. Park, D. Whittington, A. Walker, and C. Hoffer Mechanism of ritonavir changes in methadone pharmacokinetics and pharmacodynamics: I. Evidence against CYP3A mediation of methadone clearance Clin Pharmacol Ther 84 2008 497 505
34. R. DiCenzo, D.R. Peterson, K. Cruttenden, P. Mariuz, N.L. Rezk, and J. Hochreiter et al. Effects of minocycline and valproic acid coadministration on atazanavir plasma concentrations in human immunodeficiency virus-infected adults receiving atazanavir-ritonavir Antimicrob Agents Chemother 52 2008 3035 3039
35. D. Ouellet, A. Hsu, J. Qian, J.E. Lamm, J.H. Cavanaugh, and J.M. Leonard et al. Effect of fluoxetine on pharmacokinetics of ritonavir Antimicrob Agents Chemother 42 1998 3107 3112 (Pubitemid 28553726)
36. A.M. Filppula, M. Neuvonen, J. Laitila, P.J. Neuvonen, and J.T. Backman Autoinhibition of CYP3A4 leads to major role of CYP2C8 in imatinib metabolism: variability in CYP2C8 activity may alter plasma concentrations and response Drug Metab Dispos 4 2013 50 59