Contribution of CYP2E1 and CYP3A to acetaminophen reactive metabolite formation

Clinical Pharmacology and Therapeutics

Volumn 67, Issue 3, 2000, Pages 275-282

  Manyike, Peter T ^b   Kharasch, Evan D ^b   Kalhorn, Thomas F ^b   Slattery, John T ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450 3A; DIMETHYLNITROSAMINE DEMETHYLASE; N ACETYL 1,4 BENZOQUINONE IMINE; PARACETAMOL; RIFAMPICIN; THIOL DERIVATIVE;

ADULT; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG METABOLISM; DRUG OVERDOSE; DRUG URINE LEVEL; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN EXPERIMENT; LIVER MICROSOME; MALE; PRIORITY JOURNAL;

EID: 0005590750     PISSN: 00099236     EISSN: None     Source Type: Journal    
DOI: 10.1067/mcp.2000.104736     Document Type: Article

References (27)

1. 1. Albano E, Rundgren M, Harvison PJ, Nelson SD, Moldeus P. Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity. Mol Pharmacol 1985;28:306-11.
2. 2. Black M. Acetaminophen hepatotoxicity. Annu Rev Med 1984;35:577-93.
3. 3. Raucy JL, Lasker JM, Lieber CS, Black M. Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys 1989; 271:270-83.
4. 4. Patten CJ, Thomas PE, Guy RL, Lee M, Gonzalez FJ, Guengerich FP, et al. Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem Res Toxicol 1993;6: 511-8.
5. 5. Thummel KE, Lee CA, Kunze KL, Nelson SD, Slattery JT. Oxidation of acetaminophen to N-acetyl-p-aminobenzoquinone imine by human CYP3A4. Biochem Pharmacol 1993;45:1563-9.
6. 6. Sarich T, Kalhorn T, Magee S, al-Sayegh F, Adams S, Slattery J, et al. The effect of omeprazole pretreatment on acetaminophen metabolism in rapid and slow metabolizers of S-mephenytoin. Clin Pharmacol Ther 1997;62:21-8.
7. 7. Epstein MM, Nelson SD, Slattery JT, Kalhorn TF, Wall RA, Wright JM. Inhibition of the metabolism of paracetamol by isoniazid. Br J Clin Pharmacol 1991;31:139-42.
8. 8. Zand R, Nelson SD, Slattery JT, Thummel KE, Kalhorn TF, Adams SP, et al. Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther 1993;54:142-9.
9. 9. Chien JY, Thummel KE, Slattery JT. Pharmacokinetic consequences of induction of CYP2E1 by ligand stabilization. Drug Metab Dispos 1997;25:1165-75.
10. 10. Ryan DE, Ramanathan L, Iida S, Thomas PE, Haniu M, Shively JE, et al. Characterization of a major form of rat hepatic microsomal cytochrome P-450 induced by isoniazid. J Biol Chem 1985;260:6385-93.
11. 11. Koop DR, Morgan ET, Tarr GE, Coon MJ. Purification and characterization of a unique isozyme of cytochrome P-450 from liver microsomes of ethanol-treated rabbits. J Biol Chem 1982;257:8472-80.
12. 12. Rando RR. Mechanism-based enzyme inactivators. Pharmacol Rev 1984;36:111-42.
13. 13. Brady JF, Xiao F, Wang MH, Li Y, Ning SM, Gapac JM, et al. Effects of disulfiram on hepatic P450IIE1, other microsomal enzymes, and hepatotoxicity in rats. Toxicol Appl Pharmacol 1991;108:366-73.
14. 14. Kharasch ED, Hankins DC, Baxter PJ, Thummel KE. Single-dose disulfiram does not inhibit CYP2A6 activity. Clin Pharmacol Ther 1998;64:39-45.
15. 15. Kharasch ED, Hankins DC, Jubert C, Thummel KE, Taraday JK. Lack of single-dose disulfiram effects on cytochrome P-450 2C9, 2C19, 2D6, and 3A4 activities: evidence for specificity toward P-450 2E1. Drug Metab Dispos 1999;27:717-23.
16. 16. Forrest JA, Clements JA, Prescott LE Clinical pharmacokinetics of paracetamol. Clin Pharmacokinet 1982;7:93-107.
17. 17. Pichard L, Fabre I, Fabre G, Domergue J, Saint Aubert B, Mourad G, et al. Cyclosporin A drug interactions: screening for inducers and inhibitors of cytochrome P-450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metab Dispos 1990;18:595-606.
18. 18. Gillum JG, Sesler JM, Bruzzese VL, Israel DS, Polk RE. Induction of theophylline clearance by rifampin and rifabutin in healthy male volunteers. Antimicrob Agents Chemother 1996;40:1866-9.
19. 19. Nolan CM, Sandblom RE, Thummel KE, Slattery JT, Nelson SD. Hepatotoxicity associated with acetaminophen usage in patients receiving multiple drug therapy for tuberculosis. Chest 1994;105:408-11.
20. 20. Wilson JM, Slattery JT, Forte AJ, Nelson SD. Analysis of acetaminophen metabolites in urine by high-performance liquid chromatography with UV and amperometric detection. J Chromatogr 1982;227:453-62.
21. 21. Chien JY, Peter RM, Nolan CM, Wartell C, Slattery JT, Nelson SD, et al. Influence of polymorphic N-acetyl-transferase phenotype on the inhibition and induction of acetaminophen bioactivation with long-term isoniazid. Clin Pharmacol Ther 1997;61:24-34.
22. 22. Kharasch ED, Thummel KE, Mhyre J, Lillibridge JH. Single-dose disulfiram inhibition of chlorzoxazone metabolism: a clinical probe for P450 2E1. Clin Pharmacol Ther 1993;53:643-50.
23. 23. Kharasch ED, Thummel KE, Mautz D, Bosse S. Clinical enflurane metabolism by cytochrome P450 2E1. Clin Pharmacol Ther 1994;55:434-40.
24. 24. Kharasch ED, Armstrong AS, Gunn K, Artru A, Cox K, Karol MD. Clinical sevoflurane metabolism and disposition; II: the role of cytochrome P450 2E1 in fluoride and hexafluoroisopropanol formation. Anesthesiology 1995; 82:1379-88.
25. 25. Kharasch ED, Hankins D, Mautz D, Thummel KE. Identification of the enzyme responsible for oxidative halothane metabolism: implications for prevention of halothane hepatitis. Lancet 1996;347:1367-71.
26. 26. Emery M, Jubert C, Thummel KE, Kharasch ED. Duration of cytochrome P450 2E1 (CYP2E1) inhibition and estimation of functional half-life after single-dose disulfiram administration. J Pharmacol Exp Ther 1999;291:213-9.
27. 27. Chen W, Koenigs LL, Thompson SJ, Peter RM, Rettie AE, Trager WF, et al. Oxidation of acetaminophen to its toxic quinone imine and nontoxic catechol metabolites by baculovirus-expressed and purified human cytochromes P450 2E1 and 2A6. Chem Res Toxicol 1998;11:295-301.