Metabolic activation by human arylacetamide deacetylase, CYP2E1, and CYP1A2 causes phenacetin-induced methemoglobinemia

Biochemical Pharmacology

Volumn 84, Issue 9, 2012, Pages 1196-1206

  Kobayashi, Yuki ^a   Fukami, Tatsuki ^a   Higuchi, Ryota ^a   Nakajima, Miki ^a   Yokoi, Tsuyoshi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Arylacetamide deacetylase; Cytochrome P450; Methemoglobinemia; Phenacetin

Indexed keywords

ARYLACETAMIDE DEACETYLASE; CYTOCHROME P450 1A2; CYTOCHROME P450 2E1; ENZYME; ESTERASE INHIBITOR; METHEMOGLOBIN; PARA PHENETIDINE; PHENACETIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; ERYTHROCYTE; HEMOGLOBIN BLOOD LEVEL; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MALE; METABOLIC ACTIVATION; METHEMOGLOBINEMIA; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ADULT; ANALGESICS; ANIMALS; ANTIPYRETICS; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 CYP2E1; ERYTHROCYTES; HUMANS; HYDROLYSIS; MALE; METHEMOGLOBIN; METHEMOGLOBINEMIA; MICE; MICE, INBRED C57BL; MICROSOMES, LIVER; ORGANOPHOSPHONATES; PHENACETIN; PHENETIDINE; PHYSOSTIGMINE; YOUNG ADULT;

EID: 84866633738     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.08.015     Document Type: Article

References (38)

1. C.B. Jensen, and D.J. Jollow The role of N-hydroxyphenetidine in phenacetin-induced hemolytic anemia Toxicol Appl Pharmacol 111 1991 1 12
2. M. Gago-Dominguez, J.M. Yuan, J.E. Castelao, R.K. Ross, and M.C. Yu Regular use of analgesics is a risk factor for renal cell carcinoma Br J Cancer 81 1999 542 548
3. PA (P-450IA2), the phenacetin O-deethylase, is primarily responsible for the hepatic 3-demethylation of caffeine and N-oxidation of carcinogenic arylamines Proc Natl Acad Sci USA 86 1989 7696 7700
4. K. Kobayashi, M. Nakajima, K. Oshima, N. Shimada, T. Yokoi, and K. Chiba Involvement of CYP2E1 as a low-affinity enzyme in phenacetin O-deethylation in human liver microsomes Drug Metab Dispos 27 1999 860 865
5. S. Kudo, K. Umehara, M. Hosokawa, G. Miyamoto, K. Chiba, and T. Satoh Phenacetin deacetylase activity in human liver microsomes: distribution, kinetics, and chemical inhibition and stimulation J Pharmacol Exp Ther 294 2000 80 88
6. P.J. Wirth, P. Alewood, I. Calder, and S.S. Thorgeirsson Mutagenicity of N-hydroxy-2-acetylaminofluorene and N-hydroxy-phenacetin and their respective deacetylated metabolites in nitroreductase deficient Salmonella TA98FR and TA100FR Carcinogenesis 3 1982 167 170
7. T.J. Moore, C.S. Walsh, and M.R. Cohen Reported adverse event cases of methemoglobinemia associated with benzocaine products Arch Intern Med 164 2004 1192 1196
8. L.F. Rodriguez, L.M. Smolik, and A.J. Zbehlik Benzocaine-induced methemoglobinemia: report of a severe reaction and review of the literature Ann Pharmacother 28 1994 643 649
9. A. Watanabe, T. Fukami, S. Takahashi, Y. Kobayashi, N. Nakagawa, and M. Nakajima Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen Drug Metab Dispos 38 2010 1532 1537
10. A. Watanabe, T. Fukami, M. Nakajima, M. Takamiya, Y. Aoki, and T. Yokoi Human arylacetamide deacetylase is a principal enzyme in flutamide hydrolysis Drug Metab Dispos 37 2009 1513 1520
11. A. Nakajima, T. Fukami, Y. Kobayashi, A. Watanabe, M. Nakajima, and T. Yokoi Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: rifampicin, rifabutin, and rifapentine Biochem Pharmacol 82 2011 1747 1756
12. N. Nakayama, and Y. Masuda Suppression of phenacetin-induced methemoglobinemia by diethyldithiocarbamate and carbon disulfide and its relation to phenacetin metabolism in mice J Pharmacobiodyn 8 1985 868 876
13. J. Wang, B. Sun, Y. Cao, and Y. Tian Protection of wheat bran feruloyl oligosaccharides against free radical-induced oxidative damage in normal human erythrocytes Food Chem Toxicol 47 2009 1591 1599
14. Y. Kobayashi, T. Fukami, A. Nakajima, A. Watanabe, M. Nakajima, and T. Yokoi Species differences in tissue distribution and enzyme activities of arylacetamide deacetylase in human, rat, and mouse Drug Metab Dispos 40 2012 671 679
15. M. Nakajima, M. Itoh, H. Sakai, T. Fukami, M. Katoh, and H. Yamazaki CYP2A13 expressed in human bladder metabolically activates 4-aminobiphenyl Int J Cancer 119 2006 2520 2526
16. A. Yano, S. Higuchi, K. Tsuneyama, T. Fukami, M. Nakajima, and T. Yokoi Involvement of immune-related factors in diclofenac-induced acute liver injury in mice Toxicology 293 2012 107 114
17. M.M. Bradford A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal Biochem 72 1976 248 254
18. T. Fukami, M. Nakajima, H. Sakai, M. Katoh, and T. Yokoi CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin, and theophylline Drug Metab Dispos 35 2007 335 339
19. T. Fukami, S. Takahashi, N. Nakagawa, T. Maruichi, M. Nakajima, and T. Yokoi In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human carboxylesterase activities Drug Metab Dispos 38 2010 2173 2178
20. S.G. Emeigh Hart, W.P. Beierschmitt, J.B. Bartolone, D.S. Wyand, E.A. Khairallah, and S.D. Cohen Evidence against deacetylation and for cytochrome P450-mediated activation in acetaminophen-induced nephrotoxicity in the CD-1 mouse Toxicol Appl Pharmacol 107 1991 1 15
21. J. Wang, E.T. Williams, J. Bourgea, Y.N. Wong, and C.J. Patten Characterization of recombinant human carboxylesterases: fluorescein diacetate as a probe substrate for human carboxylesterase 2 Drug Metab Dispos 39 2011 1329 1333
22. H. Büch, W. Buzello, E. Heymann, and K. Krisch Inhibition of phenacetin- and acetanilide-induced methemoglobinemia in the rat by the carboxylesterase inhibitor bis-[p-nitrophenyl] phosphate Biochem Pharmacol 18 1969 801 811
23. S.D. Cohen, and S.D. Murphy Carboxylesterase inhibition as an indicator of malathione potentiation in mice J Pharmacol Exp Ther 176 1971 733 742
24. R.W. Freeman, and R.D. Harbison The role of benzoylmethylecgonine in cocaine-induced hepatotoxicity J Pharmacol Exp Ther 218 1981 558 567
25. F.P. Guengerich Cytochrome P450 and chemical toxicology Chem Res Toxicol 21 2008 70 83
26. A.D. Rodrigues Integrated cytochrome P450 reaction phenotyping: attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes Biochem Pharmacol 57 1999 465 480
27. H.C. Rawden, G.O. Kokwaro, S.A. Ward, and G. Edwards Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes Br J Clin Pharmacol 49 2000 313 322
28. M.E. Veronese, S. McLean, C.A. D'souza, and N.W. Davies Formation of reactive metabolites of phenacetin in humans and rats Xenobiotica 15 1985 929 940
29. O. Jbilo, C.F. Bartels, A. Chatonnet, J.P. Toutant, and O. Lockridge Tissue distribution of human acetylcholinesterase and butyrylcholinesterase messenger RNA Toxicon 32 1994 1445 1457
30. B. Li, M. Sedlacek, I. Manoharan, R. Boopathy, E.G. Duysen, and P. Masson Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma Biochem Pharmacol 70 2005 1673 1684
31. A.T. Guertler, and W.A. Pearce A prospective evaluation of benzocaine-associated methemoglobinemia in human beings Ann Emerg Med 24 1994 626 630
32. C. Vage, N. Saab, P.M. Woster, and C.K. Svensson Dapsone-induced hematologic toxicity: comparison of the methemoglobin-forming ability of hydroxylamine metabolites of dapsone in rat and human blood Toxicol Appl Pharmacol 129 1994 309 316
33. T.P. Reilly, P.M. Woster, and C.K. Svensson Methemoglobin formation by hydroxylamine metabolites of sulfamethoxazole and dapsone: implications for differences in adverse drug reactions J Pharmacol Exp Ther 288 1999 951 959
34. K.G. Eckert, and P. Eyer Differences in the reactions of isomeric ortho- and para-aminophenols with hemoglobin Biochem Pharmacol 32 1983 1019 1027
35. C.C. Winterbourn, B.M. McGrath, and R.W. Carrell Reactions involving superoxide and normal and unstable heamoglobins Biochem J 155 1976 493 502
36. C.C. Winterbourn, J.K. French, and R.F. Claridge Superoxide dismutase as an inhibitor of reactions of semiquinone radicals FEBS Lett 94 1978 269 272
37. A.M. Khan, N.T. Singh, and S. Bilgrami Flutamide induced methemoglobinemia J Urol 157 1997 1363
38. J.R. Jaenike Micropuncture study of methemoglobin-induced acute renal failure in the rat J Lab Clin Med 73 1969 459 468