Effect of 1-aminobenzotriazole on the in vitro metabolism and single-dose pharmacokinetics of chlorzoxazone, a selective CYP2E1 substrate in Wistar rats

References

• Balani SK, Li P, Nguyen J, Cardoza K, Zeng H, Mu DX, Wu JT, Gan LS, Lee FW. Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in guinea pigs and mice using serial sampling. Drug Metabolism and Disposition 2004; 32: 32–1095
   Google Scholar
• Balani SK, Zhu T, Yang TJ, Liu Z, He B, Lee FW. Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs and monkeys. Drug Metabolism and Disposition 2002; 30: 30–1062
   Google Scholar
• Bolt HM, Ross PH, Thier R. The cytochrome P-450 isozyme CYP2E1 in the biological processing of industrial chemicals: Consequences for occupational and environmental medicine. International Archives of Occupational and Environmental Health 2003; 76: 76–185
   Google Scholar
• Carriere V, Goasduff T, Ratanasavahh D, Morel F, Gautier JC, Guillouzo A, Beaune P, Berthou F. Both cytochrome P4502E1 and 1A1 are involved in the metabolism of chlorzoxazone. Chemical Research in Toxicology 1993; 6: 6–857
   Google Scholar
• Carriere V, Berthou F, Baird S, Belloc C, Beaune P, De Waziers I. Human cytochrome P450 2E1 (CYP2E1): From genotype to phenotype. Pharmacogenetics 1996; 6: 203–211
   PubMedGoogle Scholar
• Castillo T, Koop DR, Kamimura S, Triadafilopoulos G, Tsukamoto H. Role of cytochrome P-450 2E1 in ethanol-, carbon tetrachloride-, and iron-dependent microsomal lipid peroxidation. Hepatology 1992; 16: 16–996
   Google Scholar
• Chen L, Yang CS. Effects of cytochrome P450 2E1 modulators on the pharmacokinetics of chlorzoxazone and 6-hydroxychlorzoxazone in rats. Life Sciences 1996; 58: 58–1585
   Google Scholar
• Conney AH, Burns JJ. Physiological disposition and metabolic fate of chlorzoxazone (Paraflex) in man. Journal of Pharmacology and Experimental Therapeutics 1960; 128: 128–343
   Google Scholar
• Constan AA, Sprankle CS, Peters JM, Kedderis GL, Everitt JI, Wong BA, Gonzalez FL, Butterworth BE. Metabolism of chloroform by CYP 2E1 is required for induction of toxicity in the liver, kidney and nose of male mice. Toxicology and Applied Pharmacology 1999; 160: 160–126
   Google Scholar
• Dai Y, Rashba-Step J, Cederbaum AI. Stable expression of human cytochrome P4502E1 in HepG2 cells: Characterization of catalytic activities and production of reactive oxygen intermediates. Biochemistry 1993; 32: 32–6937
   PubMedGoogle Scholar
• Desiraju RK, Renzi NL, Jr, Nayak RK, Ng KT. Pharmacokinetics of chlorzoxazone in humans. Journal of Pharmaceutical Sciences 1983; 72: 72–994
   Google Scholar
• Di Re J, Lee C, Riddick DS. Lack of mechanism-base inactivation of rat hepatic microsomal cytochrome P450 by doxorubicin. Canadian Journal of Physiology and Pharmacology 1999; 77: 77–597
   Google Scholar
• Ekstrom G, Ingelman-Sundberg M. Rat liver microsomal NADPH-supported oxidase activity and lipid peroxidation dependent on ethanol-inducible cytochrome p-450 (P-450IIE1). Biochemistry and Pharmacology 1989; 38: 38–1319
   Google Scholar
• Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M. Antipyrine as a probe for human oxidative drug metabolism: Identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and noranti-pyrine formation. Clinical Pharmacology and Therapeutics 1996; 59: 59–623
   Google Scholar
• Garton KJ, Yuen P, Meinwald J, Thummel KE, Kharasch ED. Stereoselective metabolism of enflurane by human liver cytochrome P450 2E1. Drug Metabolism and Disposition 1995; 23: 23–1430
   Google Scholar
• Gibaldi M, Perrier D. Pharmacokinetics. Dekker, New York 1982, 2nd ed.
   Google Scholar
• Gorski JC, Jones DR, Wrighton AS, Hall SD. Contribution of human CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 1997; 27: 27–256
   Google Scholar
• Guengerich FP, Kim DH, Iwasaki M. Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects. Chemical Research in Toxicology 1991; 4: 4–179
   Google Scholar
• Huijzer JC, Adams JD, Jaw JY, Yost GS. Inhibition of 3-methylindole bioactivation by the cytochrome P450 suicide substrates 1-aminobenzotriazole and alpha-methylbenzylaminobenzotriazole. Drug Metabolism and Disposition 1989; 17: 17–42
   Google Scholar
• Jackson TE, Lilly PD, Recio L, Schlosser PM, Medinsky MA. Inhibition of cytochrome P450 2E1 decreases, but does not eliminate, genotoxicity mediated by 1,3-butadiene. Toxicological Sciences 2000; 55: 55–273
   Google Scholar
• Jayyosi Z, Knoble D, Muc M, Erick J, Thomas PE, Kelley M. Cytochrome P-450 2E1 is not the sole catalyst of chlorzoxazone hydroxylation in rat liver microsomes. The Journal of Pharmacology and Experimental Therapeutics 1995; 273: 273–1161
   PubMedGoogle Scholar
• Kharasch ED, Thummel KE, Mhyre J, Lillibridge JH. Single dose of disulfiram inhibition of chlorzoxazone metabolism: A clinical probe for P450 2E1. Clinical Pharmacology and Therapeutics 1993; 53: 53–650
   Google Scholar
• Kharasch ED, Thummel KE, Mautz D, Bosse S. Clinical enflurane metabolism by cytochrome P450 2E1. Clinical Pharmacology and Therapeutics 1994; 55: 55–440
   PubMedGoogle Scholar
• Knickle LC, Bend JR. Dose-dependent, mechanism-based inactivation of cytochrome P450 monooxygenases in vivo by 1-aminobenzotriazole in liver, lung and kidneys of untreated, Phenobarbital-treated and β-napthoflavone-treated guinea pigs. Canadian Journal of Physiology and Pharmacology 1992; 70: 70–1617
   Google Scholar
• Koop DR. Oxidative and reductive metabolism by cytochrome P450 2E1. FASEB 1992; 6: 6–730
   Google Scholar
• Lee SST, Buters JTM, Pineau T, Fernandez-Salguero P, Gonzalez FJ. Role of CYP2E1 in the hepatotoxicity of acetaminophen. Journal of Biological Chemistry 1996; 271: 271–12067
   Google Scholar
• Loi CM, Day JD, Jue SG, Bush ED, Costello P, Dewey lV, Vestal RE. Dose-dependent inhibition of theophylline metabolism by disulfiram in recovering alcoholics. Clinical Pharmacology and Therapeutics 1989; 45: 45–486
   Google Scholar
• Lucas D, Ferrara R, Gonzalez E, Bodenez P, Albores A, Manno M, Berthou R. Chlorzoxazone, a selective probe for phenotyping CYP2E1 in humans. Pharmacogenetics 1999; 9: 9–388
   PubMedGoogle Scholar
• Marczylo T, Ioannides C. Evidence for the presence of a microsomal NADH-dependent enzyme system that can bioactivate aromatic amines in the liver of rats and mice. Toxicology 1999; 134: 134–141
   Google Scholar
• Mathews JN, Raymer JH, Velez GR, Garner CE, Bucher JR. The influence of cytochrome P450 enzyme activity on the composition and quantity of volatile oranics in expired breath. Biomarkers 1996; 1: 1–201
   PubMedGoogle Scholar
• Matzke GR, Frye FR, Early JJ, Straka RJ, Carson SW. Evaluation of the influence of diabetes mellitus on antipyrine metabolism and CYP1A2 and CYP2D6 activity. Pharmacotherapy 2000; 20: 20–190
   Google Scholar
• Meschter CL, Mico BA, Mortillo M, Feldman D, Garland WA, Riley JA, Kaufman LS. A 13-week toxicologic and pathologic evaluation of prolonged cytochrome P450 inhibition by 1-aminobenzotriazole in male rats. Fundamental Applications of Toxicology 1994; 22: 22–381
   Google Scholar
• Mico BA, Federowicz DA, Ripple MG, Kerus W. In vivo inhibition of oxidative drug metabolism by and acute toxicity of 1-aminobenzotriazole (ABT). A tool for biochemical toxicology. Biochemistry and Pharmacology 1988; 37: 37–2519
   PubMedGoogle Scholar
• Mugford CA, Mortillo M, Mico BA, Tarloff JB. 1-Aminobenzotriazole destruction of hepatic and renal cytochrome P450 in male SD rats. Fundamental Applications of Toxicology 1992; 19: 19–49
   Google Scholar
• Mugford CA, Tarloff JB. Contribution of oxidative and deacetylation to the bioactivation of acetaminophen in vitro in liver and kidneys from male and female SD rats. Drug Metabolism and Disposition 1995; 23: 23–294
   Google Scholar
• Nolin TD, Gastonguay MR, Bies RR, Matzke GR, Frye RF. Impaired 6-hydroxychlorzoxazone elimination in patients with kidney disease: Implication for cytochrome P450 2E1 pharmacogenetic studies. Clinical Pharmacology and Therapeutics 2003; 74: 74–568
   Google Scholar
• Nomeir AA, Ruegg C, Shoemaker M, Favreau LV, Palamande JR, Silber P, Lin CC. Inhibition of CYP3A4 in a rapid microtiter plate assay using recombinant enzyme and in human liver microsomes using conventional substrates. Drug Metabolism and Disposition 2001; 29: 29–753
   Google Scholar
• Ono S, Hatamak T, Hotta H, Tsutsui M, Satoh T, Gonzalez FJ. Chlorzoxazone is metabolized by human CYP1A2 as well as by human CYP2E1. Pharmacogenetics 1995; 5: 5–150
   Google Scholar
• Ortiz de Montellano PR, Mathews JM. Autocatalytic alkylation of the cytochrome P450 prosthetic haem group by 1-aminobenzotriazole. Biochemical Journal 1981; 195: 195–764
   Google Scholar
• Peter R, Bocker R, Beaune PH, Iwasaki M, Guengerich FP, Yang CS. Hydroxylation of chlorzoxazone, as a specific probe for human liver cytochrome P-450 2E1. Chemical Research in Toxicology 1990; 3: 3–573
   Google Scholar
• Poloyac SM, Tosheva RT, Gardner BM, Shedlofsky SI, Blouin AR. The effect of endotoxin administration on the pharmacokinetics of chlorzoxazone in humans. Clinical Pharmacology and Therapeutics 1999; 66: 66–562
   PubMedGoogle Scholar
• Rao MNVS, Biju B, Khan AA, Mujeeb S, Mullangi R, Srinivas NR. Open access generic method for continuous determination of major human CYP 450 substrates/metabolites and its application in drug metabolism studies. Xenobiotica 2003; 33: 33–1245
   Google Scholar
• Raucy JE, Lasker JM, Lieber CS, Black M. Acetaminophen activation by human liver cytochrome P450 2E1 and 1A2. Archives in Biochemistry and Biophysics 1989; 271: 271–283
   Google Scholar
• Raucy JL, Kraner JC, Lasker JM. Bioactivation of halogenated hydrocarbons by cytochrome P4502E1. Critical Reviews in Toxicology 1993; 23: 23–20
   Google Scholar
• Rockich K, Blouin R. Effect of the acute-phase response on the pharmacokinetics of chlorzoxazone and cytochrome P-450 2E1 in vitro activity in rats. Drug Metabolism and Disposition 1999; 27: 27–1077
   Google Scholar
• Spracklin DK, Hankins DC, Fisher JM, Thummel KE, Kharasch ED. Cytochrome P4502E1 is the principal catalyst of human oxidative halothane metabolism in vitro. Journal of Pharmacology and Experimental Therapeutics 1997; 281: 281–411
   Google Scholar
• Su P, Kaushal KM, Kroetz DL. Inhibition of renal arachidonic acid omega-hydroxylase activity with ABT reduces blood pressure in the SHR. American Journal of Physiology 1998; 275: R426–438
   PubMed Web of Science ®Google Scholar
• Town C, Henderson L, Chang D, Mortillo M, Garland W. Distribution of 1-aminobenzotriazole in male rats after administration of an oral dose. Xenobiotica 1993; 23: 23–390
   Google Scholar
• Wong SG, Lin EH, Marks GS. Cytochrome sources of N-alkylprotoporphyrin IX after administration of porphyrnogenic xenobiotics to rats. Drug Metabolism and Disposition 1999; 27: 27–965
   Google Scholar
• Xu D, Voigt JM, Mico BA, Kominami S, Takemori S, Colby HD. Biochemistry Pharmacology 1994; 48: 48–1426
   Google Scholar