메뉴 건너뛰기




Volumn 23, Issue 11, 2010, Pages 1691-1700

Neutrophil- and myeloperoxidase-mediated metabolism of reduced nimesulide: Evidence for bioactivation

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; MYELOPEROXIDASE; NIMESULIDE; NUCLEOPHILE; REACTIVE NITROGEN SPECIES;

EID: 78649274348     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx1001496     Document Type: Article
Times cited : (16)

References (29)
  • 1
    • 34250807222 scopus 로고    scopus 로고
    • Nimesulide-induced hepatotoxicity and fatal hepatic failure
    • Tan, H., Ong, W. M. C., Lai, S. H., and Chow, W. C. (2007) Nimesulide-induced hepatotoxicity and fatal hepatic failure Singapore Med. J. 48, 582-585
    • (2007) Singapore Med. J. , vol.48 , pp. 582-585
    • Tan, H.1    Ong, W.M.C.2    Lai, S.H.3    Chow, W.C.4
  • 2
    • 37349002705 scopus 로고    scopus 로고
    • Liver transplantation for nonsteroidal anti-inflammatory drug-induced liver failure: Nimesulide as the first implicated compound
    • Dastis, S. N., Rahier, J., Lerut, J., and Geubel, A. P. (2007) Liver transplantation for nonsteroidal anti-inflammatory drug-induced liver failure: Nimesulide as the first implicated compound Eur. J. Gastroenterol. Hepatol. 19, 919-922
    • (2007) Eur. J. Gastroenterol. Hepatol. , vol.19 , pp. 919-922
    • Dastis, S.N.1    Rahier, J.2    Lerut, J.3    Geubel, A.P.4
  • 3
    • 0036881097 scopus 로고    scopus 로고
    • Hepatotoxicity associated with nimesulide: Data from the spanish pharmacovigilance system
    • Macia, M. A., Carvajal, A., del Pozo, J. G., Vera, E., and del Pino, A. (2002) Hepatotoxicity associated with nimesulide: Data from the spanish pharmacovigilance system Clin. Pharmacol. Ther. 72, 596-597
    • (2002) Clin. Pharmacol. Ther. , vol.72 , pp. 596-597
    • MacIa, M.A.1    Carvajal, A.2    Del Pozo, J.G.3    Vera, E.4    Del Pino, A.5
  • 5
    • 0038721790 scopus 로고    scopus 로고
    • Cohort study of hepatotoxicity associated with nimesulide and other non-steroidal anti-inflammatory drugs
    • Traversa, G., Bianchi, C., Da Cas, R., Abraha, I., Menniti-Ippolito, F., and Venegoni, M. (2003) Cohort study of hepatotoxicity associated with nimesulide and other non-steroidal anti-inflammatory drugs Br. Med. J. 327, 18-22
    • (2003) Br. Med. J. , vol.327 , pp. 18-22
    • Traversa, G.1    Bianchi, C.2    Da Cas, R.3    Abraha, I.4    Menniti-Ippolito, F.5    Venegoni, M.6
  • 6
    • 33748491500 scopus 로고    scopus 로고
    • Current status of the therapeutic uses and actions of the preferential cyclo-oxygenase-2 NSAID, nimesulide
    • Rainsford, K. D. (2006) Current status of the therapeutic uses and actions of the preferential cyclo-oxygenase-2 NSAID, nimesulide Inflammopharmacology 14, 120-137
    • (2006) Inflammopharmacology , vol.14 , pp. 120-137
    • Rainsford, K.D.1
  • 7
    • 0036051341 scopus 로고    scopus 로고
    • Mechanisms of NSAID-induced hepatotoxicity: Focus on nimesulide
    • Boelsterli, U. A. (2002) Mechanisms of NSAID-induced hepatotoxicity: Focus on nimesulide Drug Saf. 25, 633-648
    • (2002) Drug Saf. , vol.25 , pp. 633-648
    • Boelsterli, U.A.1
  • 8
    • 0031753851 scopus 로고    scopus 로고
    • Clinical pharmacokinetics of nimesulide
    • Bernareggi, A. (1998) Clinical pharmacokinetics of nimesulide Clin. Pharmacokinet. 4, 247-274
    • (1998) Clin. Pharmacokinet. , vol.4 , pp. 247-274
    • Bernareggi, A.1
  • 9
    • 61849137161 scopus 로고    scopus 로고
    • In vitro nimesulide studies toward understanding idiosyncratic hepatotoxicity: Diiminoquinone formation and conjugation
    • Li, F., Chordia, M. D., Huang, T., and Macdonald, T. L. (2009) In vitro nimesulide studies toward understanding idiosyncratic hepatotoxicity: Diiminoquinone formation and conjugation Chem. Res. Toxicol. 22, 72-80
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 72-80
    • Li, F.1    Chordia, M.D.2    Huang, T.3    MacDonald, T.L.4
  • 10
    • 33746073769 scopus 로고    scopus 로고
    • Metabolism of nomifensine to a dihydroisoquinolonium ion metabolite by human myeloperoxidase, hemoglobin, monoamine oxidase A and cytochrome P450 enzymes
    • Obach, R. S. and Dalvie, D. K. (2006) Metabolism of nomifensine to a dihydroisoquinolonium ion metabolite by human myeloperoxidase, hemoglobin, monoamine oxidase A and cytochrome P450 enzymes Drug Metab. Dispos. 34, 1310-1316
    • (2006) Drug Metab. Dispos. , vol.34 , pp. 1310-1316
    • Obach, R.S.1    Dalvie, D.K.2
  • 11
    • 0033028710 scopus 로고    scopus 로고
    • Methemoglobin formation by hydroxylamine metabolites of sulfamethoxazole and dapsone: Implications for differences in adverse drug reactions
    • Reilly, T. P., Woster, P. M., and Svensson, C. K. (1999) Methemoglobin formation by hydroxylamine metabolites of sulfamethoxazole and dapsone: Implications for differences in adverse drug reactions J. Pharmacol. Exp. Ther. 288, 951-959
    • (1999) J. Pharmacol. Exp. Ther. , vol.288 , pp. 951-959
    • Reilly, T.P.1    Woster, P.M.2    Svensson, C.K.3
  • 12
    • 33749437211 scopus 로고    scopus 로고
    • Bioactivation and hepatotoxicity of nitroaromatic drugs
    • Boelsterli, U. A., Ho, H. K., Zhou, S. F., and Leow, K. Y. (2006) Bioactivation and hepatotoxicity of nitroaromatic drugs Curr. Drug Metab. 7, 715-727
    • (2006) Curr. Drug Metab. , vol.7 , pp. 715-727
    • Boelsterli, U.A.1    Ho, H.K.2    Zhou, S.F.3    Leow, K.Y.4
  • 13
    • 45849146846 scopus 로고    scopus 로고
    • Peroxidase mediated bioactivation of hydroxylated metabolites of carbamazepine and phenytoin
    • Lu, W. and Uetrecht, J. P. (2008) Peroxidase mediated bioactivation of hydroxylated metabolites of carbamazepine and phenytoin Drug Metab. Dispos. 36, 1624-1636
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 1624-1636
    • Lu, W.1    Uetrecht, J.P.2
  • 14
    • 0030989616 scopus 로고    scopus 로고
    • Oxidation of dichlofenac to reactive intermediates by neutrophils, myeloperoxidase and hypochlorus acid
    • Miyamoto, G., Zahid, N., and Uetrecht, J. P. (1997) Oxidation of dichlofenac to reactive intermediates by neutrophils, myeloperoxidase and hypochlorus acid Chem. Res. Toxicol. 10, 414-419
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 414-419
    • Miyamoto, G.1    Zahid, N.2    Uetrecht, J.P.3
  • 15
    • 0036040079 scopus 로고    scopus 로고
    • N-oxidation of drugs associated with idiosyncratic drug reactions
    • Uetrecht, J. (2002) N-oxidation of drugs associated with idiosyncratic drug reactions Drug Metab. Rev. 34, 651-665
    • (2002) Drug Metab. Rev. , vol.34 , pp. 651-665
    • Uetrecht, J.1
  • 16
    • 25444527734 scopus 로고    scopus 로고
    • A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo
    • Gardner, I., Popovic, M., Zahid, N., and Uetrecht, J. P. (2005) A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo Chem. Res. Toxicol. 18, 1384-1394
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1384-1394
    • Gardner, I.1    Popovic, M.2    Zahid, N.3    Uetrecht, J.P.4
  • 17
    • 0027376813 scopus 로고
    • Myeloperoxidase-mediated activation of xenobiotics by human leukocytes
    • Hofstra, A. H. and Uetrecht, J. P. (1993) Myeloperoxidase-mediated activation of xenobiotics by human leukocytes Toxicology 82, 221-242
    • (1993) Toxicology , vol.82 , pp. 221-242
    • Hofstra, A.H.1    Uetrecht, J.P.2
  • 18
    • 10144260620 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: Metabolic bioactivation as a pathogenic mechanism
    • Pirmohamed, M., Madden, S., and Park, B. K. (1996) Idiosyncratic drug reactions: Metabolic bioactivation as a pathogenic mechanism Clin. Pharmacokinet. 31, 215-230
    • (1996) Clin. Pharmacokinet. , vol.31 , pp. 215-230
    • Pirmohamed, M.1    Madden, S.2    Park, B.K.3
  • 19
    • 73449143528 scopus 로고    scopus 로고
    • Myeloperoxidase: Molecular mechanisms of action and their relevance to human health and disease
    • van der Veen, B. S., de Winther, M. P. J., and Heeringa, P. (2009) Myeloperoxidase: Molecular mechanisms of action and their relevance to human health and disease Antioxid. Redox Signaling 11, 2899-2937
    • (2009) Antioxid. Redox Signaling , vol.11 , pp. 2899-2937
    • Van Der Veen, B.S.1    De Winther, M.P.J.2    Heeringa, P.3
  • 20
    • 0032881830 scopus 로고    scopus 로고
    • Metabolism of trimethoprim to a reactive iminoquinone methide by activated human neutrophils and hepatic microsomes
    • Lai, W. G., Zahid, N., and Uetrecht, J. P. (1999) Metabolism of trimethoprim to a reactive iminoquinone methide by activated human neutrophils and hepatic microsomes J. Pharmacol. Exp. Ther. 291, 292-299
    • (1999) J. Pharmacol. Exp. Ther. , vol.291 , pp. 292-299
    • Lai, W.G.1    Zahid, N.2    Uetrecht, J.P.3
  • 21
    • 0014941814 scopus 로고
    • Myeloperoxidase: Contribution to the microbicidal activity of intact leukocytes
    • Klebanoff, S. J. (1970) Myeloperoxidase: Contribution to the microbicidal activity of intact leukocytes Science 169, 1095-1097
    • (1970) Science , vol.169 , pp. 1095-1097
    • Klebanoff, S.J.1
  • 22
    • 0018860572 scopus 로고
    • Simultaneous preparation of mononuclear and polymorphonuclear leukocytes from horse blood on Ficoll-Hypaque medium
    • Ferrantei, A. and Thong, Y. H. (1980) Simultaneous preparation of mononuclear and polymorphonuclear leukocytes from horse blood on Ficoll-Hypaque medium J. Immunol. Methods 34, 279-285
    • (1980) J. Immunol. Methods , vol.34 , pp. 279-285
    • Ferrantei, A.1    Thong, Y.H.2
  • 23
    • 0026066014 scopus 로고
    • N-Chlorination and oxidation of procainamide by myeloperoxidase: Toxicological implications
    • Uetrecht, J. P. and Zahid, N. (1991) N-Chlorination and oxidation of procainamide by myeloperoxidase: Toxicological implications Chem. Res. Toxicol. 4, 218-222
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 218-222
    • Uetrecht, J.P.1    Zahid, N.2
  • 25
    • 34247399590 scopus 로고    scopus 로고
    • Unaltered hepatic oxidative phosphorylation and mitochondrial permeability transition in Wistar Rats treated with nimesulide: Relevance for nimesulide toxicity characterization
    • Moreno, A. J., Oliveira, P. J., Nova, C. D., Alvaro, A. R., Moreira, R. A., Santos, S. M. D., and Macedo, T. (2007) Unaltered hepatic oxidative phosphorylation and mitochondrial permeability transition in Wistar Rats treated with nimesulide: Relevance for nimesulide toxicity characterization J. Biochem. Mol. Toxicol. 21, 53-61
    • (2007) J. Biochem. Mol. Toxicol. , vol.21 , pp. 53-61
    • Moreno, A.J.1    Oliveira, P.J.2    Nova, C.D.3    Alvaro, A.R.4    Moreira, R.A.5    Santos, S.M.D.6    MacEdo, T.7
  • 26
    • 77952360237 scopus 로고    scopus 로고
    • Nimesulide-induced electrophile stress activates Nrf2 in human hepatocytes and mice but is not sufficient to induce hepatotoxicity in Nrf2-deficient mice
    • Kale, V., Hsiao, C. J., and Boelsterli, U. A. (2010) Nimesulide-induced electrophile stress activates Nrf2 in human hepatocytes and mice but is not sufficient to induce hepatotoxicity in Nrf2-deficient mice Chem. Res. Toxicol. 23, 967-976
    • (2010) Chem. Res. Toxicol. , vol.23 , pp. 967-976
    • Kale, V.1    Hsiao, C.J.2    Boelsterli, U.A.3
  • 27
    • 33750564770 scopus 로고    scopus 로고
    • Reactions of myeloperoxidase-derived oxidants with biological substrates: Gaining chemical insight into human inflammatory diseases
    • Pattison, D. I. and Davies, M. J. (2006) Reactions of myeloperoxidase-derived oxidants with biological substrates: Gaining chemical insight into human inflammatory diseases Curr. Med. Chem. 13, 3271-3290
    • (2006) Curr. Med. Chem. , vol.13 , pp. 3271-3290
    • Pattison, D.I.1    Davies, M.J.2
  • 28
    • 41849119477 scopus 로고    scopus 로고
    • In vitro metabolism of a model cyclopropylamine to reactive intermediate: Insights into trovafloxacin-induced hepatotoxicity
    • Sun, Q., Zhu, R., Foss, F. W., and Macdonald, T. L. (2008) In vitro metabolism of a model cyclopropylamine to reactive intermediate: Insights into trovafloxacin-induced hepatotoxicity Chem. Res. Toxicol. 21, 711-719
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 711-719
    • Sun, Q.1    Zhu, R.2    Foss, F.W.3    MacDonald, T.L.4
  • 29
    • 0027493984 scopus 로고
    • N-Chlorination of sulfamethoxazole and dapsone by the myeloperoxidase system
    • Uetrecht, J. P., Shear, N. H., and Zahid, N. (1993) N-Chlorination of sulfamethoxazole and dapsone by the myeloperoxidase system Drug Metab. Dispos. 21, 830-834
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 830-834
    • Uetrecht, J.P.1    Shear, N.H.2    Zahid, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.