Impact of time-dependent inactivation on the estimation of enzyme kinetic parameters for midazolam

Drug Metabolism Letters

Volumn 3, Issue 1, 2009, Pages 45-53

  Giragossian, Craig ^a   LaPerle, Jennifer ^a   Kosa, Rachel E ^a   Gillian, Sarah ^a  

^a PFIZER INC   (United States)

Author keywords

Enzyme kinetics; Mechanism based inactivation; Midazolam; Time dependent inactivation

Indexed keywords

MIDAZOLAM;

ARTICLE; CONTROLLED STUDY; DRUG INACTIVATION; DRUG METABOLISM; ENZYME KINETICS; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; LIVER MICROSOME; MATHEMATICAL MODEL; PRIORITY JOURNAL; TIME;

ALGORITHMS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPUTER SIMULATION; DATA INTERPRETATION, STATISTICAL; ENZYMES; HUMANS; HYPNOTICS AND SEDATIVES; KINETICS; MIDAZOLAM; MODELS, STATISTICAL; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 66149135989     PISSN: 18723128     EISSN: None     Source Type: Journal    
DOI: 10.2174/187231209787176353     Document Type: Article

References (21)

1. Bjornsson, T. D.; Callaghan, J. T.; Einolf, H. J.; Fischer, V.; Gan, L.; Grimm, S.; Kao, J.; King, S. P.; Miwa, G.; Ni, L.; Kumar, G.; McLeod, J.; Obach, S. R.; Roberts, S.; Roe, A.; Shah, A.; Snikeris, F.; Sullivan, J. T.; Tweedie, D.; Vega, J. M.; Walsh, J.; Wrighton, S. A. The conduct of in vitro and in vivo drug-drug interaction studies: a PhRMA perspective. J. Clin. Pharmacol., 2003, 43(5), 443-469.
2. Rawden, H. C.; Carlile, D. J.; Tindall, A.; Hallifax, D.; Galetin, A.; Ito, K.; Houston, J. B. Microsomal prediction of in vivo clearance and associated interindividual variability of six benzodiazepines in humans. Xenobiotica, 2005, 35(6), 603-625.
3. Patki, K. C.; Von Moltke, L. L.; Greenblatt, D. J. In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab. Dispos., 2003, 31(7), 938-944.
4. Perloff, M. D.; von Moltke, L. L.; Court, M. H.; Kotegawa, T.; Shader, R. I.; Greenblatt, D. J. Midazolam and triazolam biotransformation in mouse and human liver microsomes: relative contribution of CYP3A and CYP2C isoforms. J. Pharmacol. Exp. Ther., 2000, 292(2), 618-628.
5. Wang, R. W.; Newton, D. J.; Liu, N.; Atkins, W. M.; Lu, A. Y. Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent. Drug Metab. Dispos., 2000, 28(3), 360-366.
6. Maenpaa, J.; Hall, S. D.; Ring, B. J.; Strom, S. C.; Wrighton, S. A. Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenet., 1998, 8(2), 137-155.
7. Wandel, C.; Bocker, R. H.; Bohrer, H.; deVries, J. X.; Hofmann, W.; Walter, K.; Kleingeist, B.; Neff, S.; Ding, R.; Walter-Sack, I.; Martin, E. Relationship between hepatic cytochrome P450 3A content and activity and the disposition of midazolam administered orally. Drug Metab. Dispos., 1998, 26(2), 110-114.
8. Ghosal, A.; Satoh, H.; Thomas, P. E.; Bush, E.; Moore, D. Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cdna-expressed human cytochrome P450. Drug Metab. Dispos., 1996, 24(9), 940-947.
9. Thummel, K. E.; O'Shea, D.; Paine, M. F.; Shen, D. D.; Kunze, K. L.; Perkins, J. D.; Wilkinson, G. R. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3Amediated metabolism. Clin. Pharmacol. Ther., 1996, 59(5), 491-502.
10. Gorski, J. C.; Hall, S. D.; Jones, D. R.; VandenBranden, M.; Wrighton, S. A. Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem. Pharmacol., 1994, 47(9), 1643-1653.
11. Wrighton, S. A.; Ring, B. J. Inhibition of human CYP3A catalyzed 1'-hydroxy midazolam formation by ketoconazole, nifedipine, erythromycin, cimetidine, and nizatidine. Pharm. Res., 1994, 11(6), 921-924.
12. Kronbach, T.; Mathys, D.; Umeno, M.; Gonzalez, F. J.; Meyer, U. A. Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol. Pharmacol., 1989, 36(1), 89-96.
13. Khan, K. K.; He, Y. Q.; Domanski, T. L.; Halpert, J. R. 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., 2002, 61(3), 495-506.
14. Schrag, M. L.; Wienkers, L. C. Covalent alteration of the CYP3A4 active site: evidence for multiple substrate binding domains. Arch. Biochem. Biophys., 2001, 391(1), 49-55.
15. Podoll, W. F.; Kunze, K. L.; Thummel, K. E.; Fisher, J. M.; Trager, W. F. Evidence supporting mechanism-based inactivation of CYP3A by midazolam. ISSX Proc., 1995, 8, 154.
16. Silverman, R. B. Mechanism-based enzyme inactivators. Methods Enzymol., 1995, 249, 240-283.
17. Isin, E. M.; Guengerich, F. P. Kinetics and thermodynamics of ligand binding by cytochrome P450 3A4. J. Biol. Chem., 2006, 281(14), 9127-9136.
18. Shimada, T.; Yamazaki, H.; Mimura, M.; Inui, Y.; Guengerich, F. P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther., 1994, 270(1), 414-423.
19. Hosea, N. A.; Miller, G. P.; Guengerich, F. P. Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochem., 2000, 39(20), 5929-5939.
20. Cameron, M. D.; Wen, B.; Allen, K. E.; Roberts, A. G.; Schuman, J. T.; Campbell, A. P.; Kunze, K. L.; Nelson, S. D. Cooperative binding of midazolam with testosterone and alpha-naphthoflavone within the CYP3A4 active site: a NMR T1 paramagnetic relaxation study. Biochem., 2005, 44(43), 14143-14151.
21. Dixon, M. The determination of enzyme inhibitor constants. Biochem. J., 1953, 55(1), 170-171.