Comprehensive kinetic analysis and influence of reaction components for chlorzoxazone 6-hydroxylation in human liver microsomes with CYP antibodies

References

• Andersson TB, Sjöberg H, Hoffmann KJ, et al. (2001). An assessment of human liver-derived in vitro systems to predict the in vivo metabolism and clearance of almokalant. Drug Metab Dispos 29:712–20
   PubMed Web of Science ®Google Scholar
• Anzenbacherová E, Baranová J, Zuber R, et al. (2005). Model systems based on experimental animals for studies on drug metabolism in man: (mini)pig cytochromes P450 3A29 and 2E1. Basic Clin Pharmacol Toxicol 96:244–5
   PubMed Web of Science ®Google Scholar
• Baranová J, Anzenbacherová E, Anzenbacher P, Souček P. (2005). Minipig cytochrome P450 2E1: comparison with human enzyme. Drug Metab Dispos 33:862–5
   PubMedGoogle Scholar
• Bogaards JJP, Bertrand M, Jackson P, et al. (2000). Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, dog, micropig, monkey and man. Xenobiotica 30:1131–52
   PubMed Web of Science ®Google Scholar
• Chauret N, Gauthier A, Nicoll-Griffith DA. (1998). Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes. Drug Metab Dispos 26:1–4
   PubMed Web of Science ®Google Scholar
• Clarke SE. (1998). In vitro assessment of human cytochrome P450. Xenobiotica 28:1167–202
   PubMed Web of Science ®Google Scholar
• Court MH, Von Moltke LL, Shader RI, Greenblatt DJ. (1997). Biotransformation of chlorzoxazone by hepatic microsomes from humans and ten other mammalian species. Biopharm Drug Dispos 18:213–26
   PubMed Web of Science ®Google Scholar
• Easterbrook J, Fackett D, Li AP. (2001). A comparison of aroclor 1254-induced and uninduced rat liver microsomes to human liver microsomes in phenytoin O-deethylation, coumarin 7-hydroxylation, tolbutamide 4-hydroxylation, S-mephenytoin 4′-hydroxylation, chlorzoxazone 6-hydroxylation and testosterone 6β-hydroxylation. Chem Biol Interact 25:243–9
   Google Scholar
• Fairhead M, Giannini S, Gillam EMJ, Gilardi G. (2005). Functional characterisation of an engineered multidomain human P450 2E1 by molecular Lego. J Biol Inorg Chem 10:842–53
   PubMedGoogle Scholar
• Food and Drug Administration (FDA). (2006). Guidance for industry drug interaction studies-study design, data analysis, and implications for dosing and labeling. Rockville, MD: Center for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research (CBER)
   Google Scholar
• Fukami T, Katoh M, Yamazaki H, et al. (2008). Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: naphthalene, styrene, and toluene. Chem Res Toxicol 21:720–5
   PubMed Web of Science ®Google Scholar
• Gorski JC, Jones DR, Wrighton SA, Hall SD. (1997). Contribution of human CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 27:243–56
   PubMed Web of Science ®Google Scholar
• Guengerich FP, Kim DH, Iwasaki M. (1991). Role of human cytochrome P450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4:168–79
   PubMed Web of Science ®Google Scholar
• Hanioka N, Tanaka-Kagawa T, Miyata Y, et al. (2003). Functional characterization of three human cytochrome P450 2E1 variants with amino acid substitutions. Xenobiotica 33:575–86
   PubMed Web of Science ®Google Scholar
• Hanioka N, Yamamoto M, Tanaka-Kagawa T, et al. (2010). Functional characterization of human cytochrome P450 2E1 allelic variants: in vitro metabolism of benzene and toluene by recombinant enzymes expressed in yeast cells. Arch Toxicol 84:363–71
   PubMedGoogle Scholar
• Hickman D, Wang JP, Wang Y, Unadkat JD. (1998). Evaluation of the selectivity of in vitro probes and suitability of organic solvents for measurement of human cytochrome P450 monooxygenase activities. Drug Metab Dispos 26:207–15
   PubMed Web of Science ®Google Scholar
• Johnsrud EK, Koukouritaki SB, Divakaran K, et al. (2003). Human hepatic CYP2E1 expression during development. J Pharmacol Exp Ther 307:402–7
   PubMed Web of Science ®Google Scholar
• Kharasch ED, Hankins DC, Thummel KE. (1995). Human kidney methoxyflurane and sevoflurane metabolism: intrarenal fluoride production as a possible mechanism of methoxyflurane nephrotoxicity. Anesthesiology 82:689–99
   PubMed Web of Science ®Google Scholar
• Kharasch ED, Thummel KE. (1993). Identification of cytochrome P450 2E1 as the predominant enzyme catalyzing human liver microsomal defluorination of sevoflurane, isoflurane, and methoxyflurane. Anesthesiology 79:795–807
   PubMed Web of Science ®Google Scholar
• Koop DR. (1992). Oxidative and reductive metabolism by cytochrome P450 2E1. FASEB J 6:724–30
   PubMed Web of Science ®Google Scholar
• Koyama N, Sasabe H, Miyamoto G. (2002). Involvement of cytochrome P450 in the metabolism of rebamipide by the human liver. Xenobiotica 32:573–86
   PubMed Web of Science ®Google Scholar
• Lieber CS. (1997). Cytochrome P-4502E1: its physiological and pathological role. Physiol Rev 77:517–44
   PubMed Web of Science ®Google Scholar
• Lucas D, Ferrara R, Gonzalez E, et al. (1999). Chlorzoxazone, a selective probe for phenotyping CYP2E1 in humans. Pharmacogenetics 9:377–88
   PubMedGoogle Scholar
• Mapoles J, Berthou F, Alexander A, et al. (1993). Mammalian PC-12 cell genetically engineered for human cytochrome P450 2E1 expression. Eur J Biochem 214:735–45
   PubMedGoogle Scholar
• Nelson AC, Huang W, Moody DE. (2001). Variables in human liver microsome preparation: impact on the kinetics of L-α-acetylmethadol (LAAM) N-demethylation and dextromethorphan O-demethylation. Drug Metab Dispos 29:319–25
   PubMed Web of Science ®Google Scholar
• Ono S, Hatanaka T, Hotta H, et al. (1995). Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics 5:143–50
   PubMedGoogle Scholar
• Özdemir V, Kalow W, Tang BK, et al. (2000). Evaluation of the genetic component of variability in CYP3A4 activity: a repeated drug administration method. Pharmacogenetics 10:373–88
   PubMedGoogle Scholar
• Peter R, Böcker R, Beaune PH, et al. (1990). Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450ΙΙE1. Chem Res Toxicol 3:566–73
   PubMed Web of Science ®Google Scholar
• Schmider J, Greenblatt DJ, Von Moltke LL, et al. (1996). Characterization of six in vitro reactions mediated by human cytochrome P450: application to the testing of cytochrome P450-directed antibodies. Pharmacology 52:125–34
   PubMed Web of Science ®Google Scholar
• Shimada T, Tsumura F, Yamazaki H. (1999). Prediction of human liver microsomal oxidation of 7-ethoxycoumarin and chlorzoxazone with kinetic parameters of recombinant cytochrome P-450 enzymes. Drug Metab Dispos 27:1274–80
   PubMed Web of Science ®Google Scholar
• Shou M, Lu T, Krausz KW, et al. (2000). Use of inhibitory monoclonal antibodies to assess the contribution of cytochromes P450 to human drug metabolism. Eur J Pharmacol 394:199–209
   PubMed Web of Science ®Google Scholar
• Syme MR, Paxton JW, Keelan JA. (2004). Drug transfer and metabolism by the human placenta. Clin Pharmacokinet 43:487–514
   PubMed Web of Science ®Google Scholar
• Umehara K, Shimokawa Y, Miyamoto G. (2002). Effect of probucol on cytochrome P450 activities in human liver microsomes. Biol Pharm Bull 25:1112–14
   PubMedGoogle Scholar
• Upadhya SC, Tirumalai PS, Boyd MR, et al. (2000). Cytochrome P4502E (CYP2E) in brain: constitutive expression, induction by ethanol and localization by fluorescence in situ hybridization. Arch Biochem Biophys 373:23–34
   PubMed Web of Science ®Google Scholar
• Walsky RL, Obach RS. (2004). Validated assays for human cytochrome P450 activities. Drug Metab Dispos 32:647–60
   PubMed Web of Science ®Google Scholar
• Yin H, Racha J, Li SY, et al. (2000). Automated high throughput human CYP isoform activity assay using SPE-LC/MS method: application in CYP inhibition evaluation. Xenobiotica 30:141–54
   PubMed Web of Science ®Google Scholar
• Yuan R, Madani S, Wei XX, et al. (2002). Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab Dispos 30:1311–19
   PubMed Web of Science ®Google Scholar
• Zand R, Nelson SD, Slattery JT, et al. (1993). Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther 54:142–9
   PubMed Web of Science ®Google Scholar