Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: Midazolam, testosterone, and nifedipine

Drug Metabolism and Disposition

Volumn 31, Issue 9, 2003, Pages 1108-1116

  Galetin, Aleksandra ^a   Clarke, Stephen E ^b   Houston, J Brian ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A4; FELODIPINE; MIDAZOLAM; NIFEDIPINE; TESTOSTERONE; UK 58790; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG PROTEIN BINDING; ENZYME KINETICS; HUMAN; HUMAN CELL; LYMPHOBLAST; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN INTERACTION;

BINDING SITES; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; FELODIPINE; HUMANS; KINETICS; MIDAZOLAM; MODELS, BIOLOGICAL; NIFEDIPINE; SUBSTRATE SPECIFICITY; TESTOSTERONE; TUMOR CELLS, CULTURED;

EID: 0042357511     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.31.9.1108     Document Type: Article

References (40)

1. Atkins WM, Lu WD, and Cook DL (2002) Is there a toxicological advantage for nonhyperbolic kinetics in cytochrome P450 catalysis? J Biol Chem 277:33258-33266.
2. Domanski TL, He Y-A, Khan KK, Roussel F, Wang Q, and Halpert JR (2001) Phenylalanine and tryptophan scanning mutagenesis of CYP3A4 substrate recognition site residues and effect on substrate oxidation and cooperativity. Biochemistry 40:10150-10160.
3. Egnell A-C, Houston JB, and Boyer S (2003) In vivo heteroactivation is a possible mechanism for the drug interaction between felbamate and carbamazepine cooperativity. J Pharmacol Exp Ther 305:1251-1262.
4. Eriksson UG, Lundahl J, Bäärnhielm C, and Regårdh CG (1991) Stereoselective metabolism of felodipine in liver microsomes from rat, dog and human. Drug Metab Dispos 19:889-894.
5. Galetin A, Clarke SE, and Houston JB (2002) Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos 30:1512-1522.
6. Ghosal A, Satoh H, Thomas PE, Bush E, and Moore D (1996) Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human and cDNA-expressed human cytochrome P450. Drug Metab Dispos 24:940-947.
7. Gorski JC, Hall SD, Jones DR, Vandenbranden M, and Wrighton SA (1994) Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 47:1643-1653.
8. He YA, Roussel F, and Halpert JR (2003) Analysis of homotropic and heterotropic cooperativity of diazepam oxidation by CYP3A4 using site-directed mutagenesis and kinetic modeling. Arch Biochem Biophys 409:92-101.
9. Hosea NA, Miller GP, and Guengerich FP (2000) Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry 39:5929-5939.
10. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254.
11. Hutzler JM, Frye RF, Korzekwa KR, Branch RA, Huang S-M, and Tracy TS (2001a) Minimal in vivo activation of CYP2C9-mediated flurbiprofen metabolism by dapsone. Eur J Pharm Sci 14:47-52.
12. Hutzler JM, Hauer MJ, and Tracy TS (2001b) Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model. Drug Metab Dispos 29:1029-1034.
13. Kenworthy K, Bloomer JC, Clarke SE, and Houston JB (1999) CYP3A4 drug interactions: correlation of ten in vitro probe substrates. Br J Clin Pharmacol 48:716-727.
14. Kenworthy KE, Clarke SE, Andrews J, and Houston JB (2001) Multi-site kinetic models for CYP3A4: simultaneous activation and inhibition of diazepam and testosterone metabolism. Drug Metab Dispos 29:1-8.
15. Khan KK, He YQ, Domanski TL, and Halpert JR (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 61:495-506.
16. Korzekwa KR, Krishnamachary N, Shou M, Ogai A, Parise RA, Rettie AE, Gonzalez FJ, and Tracy TS (1998) Evaluation of atypical cytochrome P450 kinetics with two-substrute models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37:4127-4147.
17. Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, and Shou M (2001) Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos 29:368-374.
18. Lu P, Lin Y, Rodrigues AD, Rushmore TH, Baillie TA, and Shou M (2001) Testosterone, 7-benzyloxyquinoline and 7-benzyloxy-4-trifluoromethyl-coumarin bind to different domains within the active site of cytochrome P450 3A4, Drug Metab Dispos 29:1473-1479.
19. Ludwig E, Jochen S, Beschke K, and Ebner T (1999) Activation of human cytochrome P-450 3A4-catalyzed meloxicam 5′-methylhydroxylation by quinidine and hydroquinidine in vitro. J Pharmacol Exp Ther 290:1-8.
20. Mäenpää J, Hall SD, Ring BJ, Strom SC, and Wrighton SA (1998) Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by α-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 8:137-155.
21. cam. Arch Biochem Biophys 353:228-238.
22. Ngui JS, Chen Q, Shou M, Wang RW, Stearns RA, Baillie TA, and Tang W (2001) In vitro stimulation of warfarin metabolism by quinidine: increases in the formation of 4′- and 10-hydroxywarfarin. Drug Metab Dispos 29:877-886.
23. Ngui JS, Tang W, Stearns RA, Shou M, Miller RR, Zhang Y, Lin JH, and Baillie TA (2000) Cytochrome P450 3A4-mediated interaction of diclofenac and quinidine. Drug Metab Dispos 28:1043-1050.
24. Schrag ML and Wienkers LC (2001) Triazolam substrate inhibition: evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. Drug Metab Dispos 29:70-75.
25. Segel IH (1975) Enzyme Kinetics: Behaviour and Analysis of Rapid Equilibrium and Steady State Enzyme Systems. John Wiley & Sons. Inc., New York.
26. Shou M, Dai R, Cui D, Korzekwa KR, Baillie TA, and Rushmore TH (2001a) A kinetic model for the metabolic interaction of two substrates at the active site of cytochrome P450 3A4. J Biol Chem 276:2256-2262.
27. Shou M, Grogan J, Miancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV, and Korzekwa KR (1994) Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33:6450-6455.
28. Shou M, Lin Y, Lu P, Tang C, Mei Q, Cui D, Tang W, Ngui JS, Lin CC, Singh R, et al. (2001b) Enzyme kinetics of cytochrome P450-mediated reactions. Curr Drug Metab 2:17-36.
29. Shou M, Mei Q, Ettore W Jr, Dai R, Baillie T, and Rushmore TH (1999) Sigmoidal kinetic model for two cooperative substrate-binding sites in a cytochrome P450 3A4 active site: an example of the metabolism of diazepam and its derivatives. Biochem J 340:845-853
30. Soons PA, Mulders TM, Uchida E, Schoemaker HC, Cohen AF, and Breimer DD (1993) Stereoselective pharmacokinetics of oral felodipine and nitrendipine in healthy subjects: correlation with nifedipine pharmacokinetics. Eur J Clin Pharmacol 44:163-169.
31. Stone AN, Mackenzie PI, Galetin A, Houston JB, and Miners JO (2003) Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human UDP-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 31:1086-1089.
32. Stresser DM, Blanchard AP, Turner SD, Erve JC, Dandeneau AA, Miller VP, and Crespi CL (2000) Substrate-dependent modulation of CYP3A4 catalytic activity: analysis of 27 test compounds with four fluorometric substrates. Drug Metab Dispos 28:1440-1448.
33. Tang W and Stearns RA (2001) Heterotropic cooperativity of cytochrome P450 3A4 and potential drug-drug interactions. Curr Drug Metab 2:185-198.
34. Tang W, Stearns RA, Kwei GY, Iliff SA, Miller RR, Egan MA, Yu NX, Dean DC, Kumar S, Shou M, et al. (1999) Interaction of diclofenac and quinidine in monkeys: stimulation of diclofenac metabolism. J Pharmacol Exp Ther 291:1068-1074.
35. Ueng Y-F, Kuwabara T, Chun Y-J, and Guengerich FP (1997) Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Biochemistry 36:370-381.
36. Venkatakrishnan K, von Moltke LL, Court MH, Harmatz JS, Crespi CL, and Greenblat DJ (2000) Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metab Dispos 28:1493-1504.
37. Wang RW, Newton DJ, Liu N, Atkins WM, and Lu AYH (2000) Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent. Drug Metab Dispos 28:360-366.
38. Wang RW, Newton DJ, Scheri TD, and Lu AYH (1997) Human cytochrome P450 3A4-catalyzed testosterone 6β-hydroxylation and erythromycin N-demethylation. Drug Metab Dispos 25:502-507.
39. Williams JA, Ring BJ, Cantrell VE, Campanelle K, Jones DR, Hall SD, and Wrighton SA (2002) Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes. Drug Metab Dispos 30:1266-1273.
40. Yuan R, Madani S, Wei X-X, Reynolds K, and Huang S-M (2002) Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab Dispos 30:1311-1319.