메뉴 건너뛰기




Volumn 26, Issue 8, 2013, Pages 1139-1155

Metabolism of xenobiotic carboxylic acids: Focus on coenzyme a conjugation, reactivity, and interference with lipid metabolism

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; ARACHIDONIC ACID; BEZAFIBRATE; CARBON DIOXIDE; CARBOXYLIC ACID DERIVATIVE; CARNITINE; COENZYME A; CYTOCHROME P450; DOCOSAHEXAENOIC ACID; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; GLUTATHIONE; IBUPROFEN; LIPID; LONG CHAIN FATTY ACID COENZYME A LIGASE; NAFENOPIN; OCTANOIC ACID; OXYGEN; PALMITIC ACID; PIOGLITAZONE; PROPIONIC ACID; RECOMBINANT CYTOCHROME P450; RECOMBINANT ENZYME; ROSIGLITAZONE; TRIACYLGLYCEROL; TROGLITAZONE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALPROIC ACID; XENOBIOTIC AGENT; XENOBIOTIC CARBOXYLIC ACID DERIVATIVE;

EID: 84882632557     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400183y     Document Type: Article
Times cited : (55)

References (89)
  • 1
    • 84882729031 scopus 로고    scopus 로고
    • Food and Drug Administration, Center for Drug Evaluation and Research (CDER) Guidance for Industry: Safety Testing of Drug Metabolites, FDA, Silver Spring, MD
    • Food and Drug Administration, Center for Drug Evaluation and Research (CDER) (2008) Guidance for Industry: Safety Testing of Drug Metabolites, FDA, Silver Spring, MD.
    • (2008)
  • 2
    • 0035996572 scopus 로고    scopus 로고
    • Xenobiotic acyl glucuronides and acyl CoA thioesters as protein-reactive metabolites with the potential to cause idiosyncratic drug reactions
    • Boelsterli, U. A. (2002) Xenobiotic acyl glucuronides and acyl CoA thioesters as protein-reactive metabolites with the potential to cause idiosyncratic drug reactions Curr. Drug Metab. 3, 439-450
    • (2002) Curr. Drug Metab. , vol.3 , pp. 439-450
    • Boelsterli, U.A.1
  • 4
    • 84863945079 scopus 로고    scopus 로고
    • Metabolic activation of mefenamic acid leading to mefenamyl-S-acyl- glutathione adduct formation in vitro and in vivo in rat
    • Grillo, M. P., Lohr, M. T., and Wait, J. C. M. (2012) Metabolic activation of mefenamic acid leading to mefenamyl-S-acyl-glutathione adduct formation in vitro and in vivo in rat Drug Metab. Dispos. 40, 1515-1526
    • (2012) Drug Metab. Dispos. , vol.40 , pp. 1515-1526
    • Grillo, M.P.1    Lohr, M.T.2    Wait, J.C.M.3
  • 5
    • 0344837751 scopus 로고    scopus 로고
    • In vitro studies on the chemical reactivity of 2,4-dichlorophenoxyacetyl- S-acyl-CoA thioester
    • Li, C., Grillo, M. P., and Benet, L. Z. (2003) In vitro studies on the chemical reactivity of 2,4-dichlorophenoxyacetyl-S-acyl-CoA thioester Toxicol. Appl. Pharmacol. 187, 101-109
    • (2003) Toxicol. Appl. Pharmacol. , vol.187 , pp. 101-109
    • Li, C.1    Grillo, M.P.2    Benet, L.Z.3
  • 6
    • 34247381161 scopus 로고    scopus 로고
    • Studies on the metabolism of tolmetin to the chemically reactive acyl-coenzyme A thioester intermediate in rats
    • Olsen, J., Li, C., Skonberg, C., Bjørnsdottir, I., Sidenius, U., Benet, L. Z., and Hansen, S. H. (2007) Studies on the metabolism of tolmetin to the chemically reactive acyl-coenzyme A thioester intermediate in rats Drug Metab. Dispos. 35, 758-764
    • (2007) Drug Metab. Dispos. , vol.35 , pp. 758-764
    • Olsen, J.1    Li, C.2    Skonberg, C.3    Bjørnsdottir, I.4    Sidenius, U.5    Benet, L.Z.6    Hansen, S.H.7
  • 8
    • 79952702137 scopus 로고    scopus 로고
    • Drug-induced toxicity on mitochondria and lipid metabolism: Mechanistic diversity and deleterious consequences for the liver
    • Begriche, K., Massart, J., Robin, M. A., Borgne-Sanchez, A., and Fromenty, B. (2011) Drug-induced toxicity on mitochondria and lipid metabolism: Mechanistic diversity and deleterious consequences for the liver J. Hepatol. 54, 773-794
    • (2011) J. Hepatol. , vol.54 , pp. 773-794
    • Begriche, K.1    Massart, J.2    Robin, M.A.3    Borgne-Sanchez, A.4    Fromenty, B.5
  • 9
    • 53549096792 scopus 로고    scopus 로고
    • Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes
    • Grillo, M. P. and Hua, F. (2008) Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes Chem. Res. Toxicol. 21, 1749-1759
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1749-1759
    • Grillo, M.P.1    Hua, F.2
  • 10
    • 66449102106 scopus 로고    scopus 로고
    • Covalent binding of phenylacetic acid to protein in incubations with freshly isolated rat hepatocytes
    • Grillo, M. P. and Lohr, M. T. (2009) Covalent binding of phenylacetic acid to protein in incubations with freshly isolated rat hepatocytes Drug Metab. Dispos. 37, 1073-1082
    • (2009) Drug Metab. Dispos. , vol.37 , pp. 1073-1082
    • Grillo, M.P.1    Lohr, M.T.2
  • 11
    • 73149114171 scopus 로고    scopus 로고
    • Stereoselective flunoxaprofen-S-acyl-glutathione thioester formation mediated by acyl-CoA formation in rat hepatocytes
    • Grillo, M. P., Wait, J. C. M., Lohr, M. T., Khera, S., and Benet, L. Z. (2010) Stereoselective flunoxaprofen-S-acyl-glutathione thioester formation mediated by acyl-CoA formation in rat hepatocytes Drug Metab. Dispos. 38, 133-142
    • (2010) Drug Metab. Dispos. , vol.38 , pp. 133-142
    • Grillo, M.P.1    Wait, J.C.M.2    Lohr, M.T.3    Khera, S.4    Benet, L.Z.5
  • 12
    • 0036851821 scopus 로고    scopus 로고
    • Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes
    • Li, C., Benet, L. Z., and Grillo, M. P. (2002) Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes Chem. Res. Toxicol. 15, 1480-1487
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1480-1487
    • Li, C.1    Benet, L.Z.2    Grillo, M.P.3
  • 13
    • 0037381306 scopus 로고    scopus 로고
    • In vivo mechanistic studies on the metabolic activation of 2-phenylpropionic acid in rat
    • Li, C., Grillo, M. P., and Benet, L. Z. (2003) In vivo mechanistic studies on the metabolic activation of 2-phenylpropionic acid in rat J. Pharmacol. Exp. Ther. 305, 250-256
    • (2003) J. Pharmacol. Exp. Ther. , vol.305 , pp. 250-256
    • Li, C.1    Grillo, M.P.2    Benet, L.Z.3
  • 14
    • 0037518291 scopus 로고    scopus 로고
    • Covalent binding of 2-phenylpropionyl-s-acyl-CoA thioester to tissue proteins in vitro
    • Li, C., Olurinde, M. O., Hodges, L. M., Grillo, M. P., and Benet, L. Z. (2003) Covalent binding of 2-phenylpropionyl-s-acyl-CoA thioester to tissue proteins in vitro Drug Metab. Dispos. 31, 727-730
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 727-730
    • Li, C.1    Olurinde, M.O.2    Hodges, L.M.3    Grillo, M.P.4    Benet, L.Z.5
  • 15
    • 41549115474 scopus 로고    scopus 로고
    • Differential effects of fibrates on the metabolic activation of 2-phenylpropionic acid in rats
    • Li, C., Grillo, M. P., Badagnani, I., Fife, K. L., and Benet, L. Z. (2008) Differential effects of fibrates on the metabolic activation of 2-phenylpropionic acid in rats Drug Metab. Dispos. 36, 682-687
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 682-687
    • Li, C.1    Grillo, M.P.2    Badagnani, I.3    Fife, K.L.4    Benet, L.Z.5
  • 16
    • 84875152123 scopus 로고    scopus 로고
    • Characterization of the acyl-adenylate linked metabolite of mefenamic acid
    • Horng, H. and Benet, L. Z. (2013) Characterization of the acyl-adenylate linked metabolite of mefenamic acid Chem. Res. Toxicol. 26, 465-476
    • (2013) Chem. Res. Toxicol. , vol.26 , pp. 465-476
    • Horng, H.1    Benet, L.Z.2
  • 17
    • 0037495951 scopus 로고    scopus 로고
    • Identification of coenzyme A-related tolmetin metabolites in rats: Relationship with reactive drug metabolites
    • Olsen, J., Bjørnsdottir, I., and Honoré Hansen, S. (2003) Identification of coenzyme A-related tolmetin metabolites in rats: Relationship with reactive drug metabolites Xenobiotica 33, 561-570
    • (2003) Xenobiotica , vol.33 , pp. 561-570
    • Olsen, J.1    Bjørnsdottir, I.2    Honoré Hansen, S.3
  • 18
    • 32944482358 scopus 로고    scopus 로고
    • In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats
    • Olsen, J., Li, C., Bjørnsdottir, I., Sidenius, U., Hansen, S. H., and Benet, L. Z. (2005) In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats Chem. Res. Toxicol. 18, 1729-1736
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1729-1736
    • Olsen, J.1    Li, C.2    Bjørnsdottir, I.3    Sidenius, U.4    Hansen, S.H.5    Benet, L.Z.6
  • 19
    • 34547154782 scopus 로고    scopus 로고
    • Amino acid conjugation: Contribution to the metabolism and toxicity of xenobiotic carboxylic acids
    • Knights, K. M., Sykes, M. J., and Miners, J. O. (2007) Amino acid conjugation: contribution to the metabolism and toxicity of xenobiotic carboxylic acids Expert Opin. Drug Metab. Toxicol. 3, 159-168
    • (2007) Expert Opin. Drug Metab. Toxicol. , vol.3 , pp. 159-168
    • Knights, K.M.1    Sykes, M.J.2    Miners, J.O.3
  • 20
    • 34547154782 scopus 로고    scopus 로고
    • Amino acid conjugation: Contribution to the metabolism and toxicity of xenobiotic carboxylic acids
    • Knights, K. M., Sykes, M. J., and Miners, J. O. (2007) Amino acid conjugation: Contribution to the metabolism and toxicity of xenobiotic carboxylic acids Expert Opin. Drug Metab. Toxicol. 3, 159-168
    • (2007) Expert Opin. Drug Metab. Toxicol. , vol.3 , pp. 159-168
    • Knights, K.M.1    Sykes, M.J.2    Miners, J.O.3
  • 21
    • 79956269497 scopus 로고    scopus 로고
    • Characterization of non-enzymatic acylation of amino or thiol groups of bionucleophiles by the acyl-adenylate or acyl-CoA thioester of cholic acid
    • Mitamura, K., Aoyama, E., Sakai, T., Iida, T., Hofmann, A. F., and Ikegawa, S. (2011) Characterization of non-enzymatic acylation of amino or thiol groups of bionucleophiles by the acyl-adenylate or acyl-CoA thioester of cholic acid Anal. Bioanal Chem. 400, 2253-2259
    • (2011) Anal. Bioanal Chem. , vol.400 , pp. 2253-2259
    • Mitamura, K.1    Aoyama, E.2    Sakai, T.3    Iida, T.4    Hofmann, A.F.5    Ikegawa, S.6
  • 22
    • 0035580993 scopus 로고    scopus 로고
    • Nafenopin-, ciprofibroyl-, and palmitoyl-CoA conjugation in vitro: Kinetic and molecular characterization of marmoset liver microsomes and expressed MLCL1
    • Drogemuller, C. J., Nunthasomboon, S., and Knights, K. M. (2001) Nafenopin-, ciprofibroyl-, and palmitoyl-CoA conjugation in vitro: Kinetic and molecular characterization of marmoset liver microsomes and expressed MLCL1 Arch. Biochem. Biophys. 396, 56-64
    • (2001) Arch. Biochem. Biophys. , vol.396 , pp. 56-64
    • Drogemuller, C.J.1    Nunthasomboon, S.2    Knights, K.M.3
  • 24
    • 37249092959 scopus 로고    scopus 로고
    • Evidence for 26 distinct acyl-coenzyme A synthetase genes in the human genome
    • Watkins, P. A., Maiguel, D., Jia, Z., and Pevsner, J. (2007) Evidence for 26 distinct acyl-coenzyme A synthetase genes in the human genome J. Lipid Res. 48, 2736-2750
    • (2007) J. Lipid Res. , vol.48 , pp. 2736-2750
    • Watkins, P.A.1    Maiguel, D.2    Jia, Z.3    Pevsner, J.4
  • 25
    • 0034232476 scopus 로고    scopus 로고
    • Xenobiotic-CoA ligases: Kinetic and molecular characterization
    • Knights, K. M. and Drogemuller, C. J. (2000) Xenobiotic-CoA ligases: Kinetic and molecular characterization Curr. Drug Metab. 1, 49-66
    • (2000) Curr. Drug Metab. , vol.1 , pp. 49-66
    • Knights, K.M.1    Drogemuller, C.J.2
  • 26
    • 70349612067 scopus 로고    scopus 로고
    • Comparative analyses of disease risk genes belonging to the Acyl-CoA synthetase medium-chain (ACSM) family in human liver and cell lines
    • Boomgaarden, I., Vock, C., Klapper, M., and Döring, F. (2009) Comparative analyses of disease risk genes belonging to the Acyl-CoA synthetase medium-chain (ACSM) family in human liver and cell lines Biochem. Genet. 47, 739-748
    • (2009) Biochem. Genet. , vol.47 , pp. 739-748
    • Boomgaarden, I.1    Vock, C.2    Klapper, M.3    Döring, F.4
  • 27
    • 33748752324 scopus 로고    scopus 로고
    • Rat long-chain acyl-CoA synthetase mRNA, protein, and activity vary in tissue distribution and in response to diet
    • Mashek, D. G., Li, L. O., and Coleman, R. A. (2006) Rat long-chain acyl-CoA synthetase mRNA, protein, and activity vary in tissue distribution and in response to diet J. Lipid Res. 47, 2004-2010
    • (2006) J. Lipid Res. , vol.47 , pp. 2004-2010
    • Mashek, D.G.1    Li, L.O.2    Coleman, R.A.3
  • 28
    • 79953655654 scopus 로고    scopus 로고
    • Drug-s-acyl-glutathione thioesters: Synthesis, bioanalytical properties, chemical reactivity, biological formation and degradation
    • Grillo, M. P. (2011) Drug-s-acyl-glutathione thioesters: Synthesis, bioanalytical properties, chemical reactivity, biological formation and degradation Curr. Drug Metab. 12, 229-244
    • (2011) Curr. Drug Metab. , vol.12 , pp. 229-244
    • Grillo, M.P.1
  • 29
    • 0035816532 scopus 로고    scopus 로고
    • Acyl-CoA synthetase isoforms 1, 4, and 5 are present in different subcellular membranes in rat liver and can be inhibited independently
    • Lewin, T. M., Kim, J.-H., Granger, D. A., Vance, J. E., and Coleman, R. A. (2001) Acyl-CoA synthetase isoforms 1, 4, and 5 are present in different subcellular membranes in rat liver and can be inhibited independently J. Biol. Chem. 276, 24674-24679
    • (2001) J. Biol. Chem. , vol.276 , pp. 24674-24679
    • Lewin, T.M.1    Kim, J.-H.2    Granger, D.A.3    Vance, J.E.4    Coleman, R.A.5
  • 30
    • 43249086785 scopus 로고    scopus 로고
    • Mammalian long-chain acyl-CoA synthetases
    • Soupene, E. and Kuypers, F. A. (2008) Mammalian long-chain acyl-CoA synthetases Exp. Biol. Med. 233, 507-521
    • (2008) Exp. Biol. Med. , vol.233 , pp. 507-521
    • Soupene, E.1    Kuypers, F.A.2
  • 31
    • 0030438696 scopus 로고    scopus 로고
    • Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human liver microsomes and nine recombinant human cytochromes P450
    • Zhao, X. J., Yokoyama, H., Chiba, K., Wanwimolruk, S., and Ishizaki, T. (1996) Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human liver microsomes and nine recombinant human cytochromes P450 J. Pharmacol. Exp. Ther. 279, 1327-1334
    • (1996) J. Pharmacol. Exp. Ther. , vol.279 , pp. 1327-1334
    • Zhao, X.J.1    Yokoyama, H.2    Chiba, K.3    Wanwimolruk, S.4    Ishizaki, T.5
  • 32
    • 8844224917 scopus 로고    scopus 로고
    • Effects of β-estradiol and propofol on the 4-methylumbelliferone glucuronidation in recombinant human UGT isozymes 1A1, 1A8 and 1A9
    • Mano, Y., Usui, T., and Kamimura, H. (2004) Effects of β-estradiol and propofol on the 4-methylumbelliferone glucuronidation in recombinant human UGT isozymes 1A1, 1A8 and 1A9 Biopharm. Drug Dispos. 25, 339-344
    • (2004) Biopharm. Drug Dispos. , vol.25 , pp. 339-344
    • Mano, Y.1    Usui, T.2    Kamimura, H.3
  • 33
    • 0035816590 scopus 로고    scopus 로고
    • Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones
    • Kim, J. H., Lewin, T. M., and Coleman, R. A. (2001) Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones J. Biol. Chem. 276, 24667-24673
    • (2001) J. Biol. Chem. , vol.276 , pp. 24667-24673
    • Kim, J.H.1    Lewin, T.M.2    Coleman, R.A.3
  • 34
    • 78651374376 scopus 로고    scopus 로고
    • Valproate uncompetitively inhibits arachidonic acid acylation by rat acyl-CoA synthetase 4: Relevance to valproate's efficacy against bipolar disorder
    • Shimshoni, J. A., Basselin, M., Li, L. O., Coleman, R. A., Rapoport, S. I., and Modi, H. R. (2011) Valproate uncompetitively inhibits arachidonic acid acylation by rat acyl-CoA synthetase 4: Relevance to valproate's efficacy against bipolar disorder Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1811, 163-169
    • (2011) Biochim. Biophys. Acta Mol. Cell Biol. Lipids , vol.1811 , pp. 163-169
    • Shimshoni, J.A.1    Basselin, M.2    Li, L.O.3    Coleman, R.A.4    Rapoport, S.I.5    Modi, H.R.6
  • 35
    • 0027471547 scopus 로고
    • Metabolic inversion of (R)-ibuprofen: Formation of ibuprofenyl-coenzyme A
    • Tracy, T. S., Wirthwein, D. P., and Hall, S. D. (1993) Metabolic inversion of (R)-ibuprofen: Formation of ibuprofenyl-coenzyme A Drug Metab. Dispos. 21, 114-120
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 114-120
    • Tracy, T.S.1    Wirthwein, D.P.2    Hall, S.D.3
  • 36
    • 0028262304 scopus 로고
    • Xenobiotic acyl-CoA formation: Evidence of kinetically distinct hepatic microsomal long-chain fatty acid and nafenopin-CoA ligases
    • Knights, K. M. and Roberts, B. J. (1994) Xenobiotic acyl-CoA formation: Evidence of kinetically distinct hepatic microsomal long-chain fatty acid and nafenopin-CoA ligases Chem.-Biol. Interact. 90, 215-224
    • (1994) Chem.-Biol. Interact. , vol.90 , pp. 215-224
    • Knights, K.M.1    Roberts, B.J.2
  • 37
    • 0036136379 scopus 로고    scopus 로고
    • Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro
    • Grillo, M. P. and Benet, L. Z. (2002) Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro Drug Metab. Dispos. 30, 55-62
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 55-62
    • Grillo, M.P.1    Benet, L.Z.2
  • 38
    • 0036802060 scopus 로고    scopus 로고
    • Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites
    • Li, C., Benet, L. Z., and Grillo, M. P. (2002) Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites Chem. Res. Toxicol. 15, 1309-1317
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1309-1317
    • Li, C.1    Benet, L.Z.2    Grillo, M.P.3
  • 39
    • 1642457324 scopus 로고    scopus 로고
    • In vitro reactivity of carboxylic acid-CoA thioesters with glutathione
    • Sidenius, U., Skonberg, C., Olsen, J., and Hansen, S. H. (2004) In vitro reactivity of carboxylic acid-CoA thioesters with glutathione Chem. Res. Toxicol. 17, 75-81
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 75-81
    • Sidenius, U.1    Skonberg, C.2    Olsen, J.3    Hansen, S.H.4
  • 40
    • 0142150004 scopus 로고    scopus 로고
    • Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile
    • Grillo, M. P. and Hua, F. (2003) Identification of zomepirac-S-acyl- glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile Drug Metab. Dispos. 31, 1429-1436
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 1429-1436
    • Grillo, M.P.1    Hua, F.2
  • 41
    • 0142212151 scopus 로고    scopus 로고
    • Studies on the chemical reactivity of diclofenac acyl glucuronide with glutathione: Identification of diclofenac-S-acyl-glutathione in rat bile
    • Grillo, M. P., Knutson, C. G., Sanders, P. E., Waldon, D. J., Hua, F., and Ware, J. A. (2003) Studies on the chemical reactivity of diclofenac acyl glucuronide with glutathione: identification of diclofenac-S-acyl-glutathione in rat bile Drug Metab. Dispos. 31, 1327-1336
    • (2003) Drug Metab. Dispos. , vol.31 , pp. 1327-1336
    • Grillo, M.P.1    Knutson, C.G.2    Sanders, P.E.3    Waldon, D.J.4    Hua, F.5    Ware, J.A.6
  • 42
    • 0037142356 scopus 로고    scopus 로고
    • Chemical reactivity of the naproxen acyl glucuronide and the naproxen coenzyme A thioester towards bionucleophiles
    • Olsen, J., Bjørnsdottir, I., Tjørnelund, J., and Hansen, S. H. (2002) Chemical reactivity of the naproxen acyl glucuronide and the naproxen coenzyme A thioester towards bionucleophiles J. Pharm. Biomed. Anal. 29, 7-15
    • (2002) J. Pharm. Biomed. Anal. , vol.29 , pp. 7-15
    • Olsen, J.1    Bjørnsdottir, I.2    Tjørnelund, J.3    Hansen, S.H.4
  • 43
    • 0028837297 scopus 로고
    • Characterization and formation of the glutathione conjugate of clofibric acid
    • Shore, L. J., Fenselau, C., King, A. R., and Dickinson, R. G. (1995) Characterization and formation of the glutathione conjugate of clofibric acid Drug Metab. Dispos. 23, 119-123
    • (1995) Drug Metab. Dispos. , vol.23 , pp. 119-123
    • Shore, L.J.1    Fenselau, C.2    King, A.R.3    Dickinson, R.G.4
  • 44
    • 0029129057 scopus 로고
    • Drug safety discontinuations in the United Kingdom, the United States, and Spain from 1974 through 1993: A regulatory perspective
    • Bakke, O. M., Manocchia, M., de Abajo, F., Kaitin, K. I., and Lasagna, L. (1995) Drug safety discontinuations in the United Kingdom, the United States, and Spain from 1974 through 1993: a regulatory perspective Clin. Pharmacol. Ther. 58, 108-117
    • (1995) Clin. Pharmacol. Ther. , vol.58 , pp. 108-117
    • Bakke, O.M.1    Manocchia, M.2    De Abajo, F.3    Kaitin, K.I.4    Lasagna, L.5
  • 45
    • 9444229982 scopus 로고    scopus 로고
    • Liver injury induced by the non-steroidal anti-inflammatory drug mefenamic acid
    • Somchit, N., Sanat, F., Gan, E. H., Shahrin, I. A. W., and Zuraini, A. (2004) Liver injury induced by the non-steroidal anti-inflammatory drug mefenamic acid Singapore Med. J. 45, 530-532
    • (2004) Singapore Med. J. , vol.45 , pp. 530-532
    • Somchit, N.1    Sanat, F.2    Gan, E.H.3    Shahrin, I.A.W.4    Zuraini, A.5
  • 46
    • 77955627127 scopus 로고    scopus 로고
    • Increased risk of hospitalization for acute hepatitis in patients with previous exposure to NSAIDs
    • Lee, C. H., Wang, J. D., and Chen, P. C. (2010) Increased risk of hospitalization for acute hepatitis in patients with previous exposure to NSAIDs Pharmacoepidemiol. Drug Saf. 19, 708-714
    • (2010) Pharmacoepidemiol. Drug Saf. , vol.19 , pp. 708-714
    • Lee, C.H.1    Wang, J.D.2    Chen, P.C.3
  • 47
    • 14044263396 scopus 로고    scopus 로고
    • Application of quantitative structure-toxicity relationships for acute NSAID cytotoxicity in rat hepatocytes
    • Siraki, A. G., Chevaldina, T., and O'Brien, P. J. (2005) Application of quantitative structure-toxicity relationships for acute NSAID cytotoxicity in rat hepatocytes Chem.-Biol. Interact. 151, 177-191
    • (2005) Chem.-Biol. Interact. , vol.151 , pp. 177-191
    • Siraki, A.G.1    Chevaldina, T.2    O'Brien, P.J.3
  • 49
    • 0030923886 scopus 로고    scopus 로고
    • 'Golf ball liver': Agent orange hepatitis
    • Leonard, C., Burke, C. M., O'Keane, C., and Doyle, J. S. (1997) 'Golf ball liver': Agent orange hepatitis Gut 40, 687-688
    • (1997) Gut , vol.40 , pp. 687-688
    • Leonard, C.1    Burke, C.M.2    O'Keane, C.3    Doyle, J.S.4
  • 50
    • 0027292101 scopus 로고
    • Acyl-CoA synthetase mRNA expression is controlled by fibric-acid derivatives, feeding and liver proliferation
    • Schoonjans, K., Staels, B., Grimaldi, P., and Auwerx, J. (1993) Acyl-CoA synthetase mRNA expression is controlled by fibric-acid derivatives, feeding and liver proliferation Eur. J. Biochem. 216, 615-622
    • (1993) Eur. J. Biochem. , vol.216 , pp. 615-622
    • Schoonjans, K.1    Staels, B.2    Grimaldi, P.3    Auwerx, J.4
  • 51
    • 0028232515 scopus 로고
    • Relationship between plasma lipids and palmitoyl-CoA hydrolase and synthetase activities with peroxisomal proliferation in rats treated with fibrates
    • Alegret, M., Ferrando, R., Vazquez, M., Adzet, T., Merlos, M., and Laguna, J. C. (1994) Relationship between plasma lipids and palmitoyl-CoA hydrolase and synthetase activities with peroxisomal proliferation in rats treated with fibrates Br. J. Pharmacol. 112, 551-556
    • (1994) Br. J. Pharmacol. , vol.112 , pp. 551-556
    • Alegret, M.1    Ferrando, R.2    Vazquez, M.3    Adzet, T.4    Merlos, M.5    Laguna, J.C.6
  • 52
    • 84882692429 scopus 로고    scopus 로고
    • DailyMed, (accessed Oct)
    • DailyMed, http://dailymed.nlm.nih.gov/dailymed/about.cfm?CFID= 24634960&CFTOKEN=a143b2b0cf8a571f-D429041D-F5C5-F2B8- 7A03CEF43F77CDD3&jsessionid=8430601e71298b08962b465aa6530417d503 (accessed Oct, 2012).
    • (2012)
  • 53
    • 0028865215 scopus 로고
    • Xenobiotic lipids: The inclusion of xenobiotic compounds in pathways of lipid biosynthesis
    • Dodds, P. F. (1995) Xenobiotic lipids: the inclusion of xenobiotic compounds in pathways of lipid biosynthesis Prog. Lipid Res. 34, 219-247
    • (1995) Prog. Lipid Res. , vol.34 , pp. 219-247
    • Dodds, P.F.1
  • 54
    • 0029127584 scopus 로고
    • Inhibition of mitochondrial beta-oxidation as a mechanism of hepatotoxicity
    • Fromenty, B. and Pessayre, D. (1995) Inhibition of mitochondrial beta-oxidation as a mechanism of hepatotoxicity Pharmacol. Ther. 67, 101-154
    • (1995) Pharmacol. Ther. , vol.67 , pp. 101-154
    • Fromenty, B.1    Pessayre, D.2
  • 55
    • 0032490937 scopus 로고    scopus 로고
    • Triclosan targets lipid synthesis
    • McMurry, L. M., Oethinger, M., and Levy, S. B. (1998) Triclosan targets lipid synthesis Nature 394, 531-532
    • (1998) Nature , vol.394 , pp. 531-532
    • McMurry, L.M.1    Oethinger, M.2    Levy, S.B.3
  • 56
    • 21244461963 scopus 로고    scopus 로고
    • Triclosan inhibition of fatty acid synthesis and its effect on growth of Escherichia coli and Pseudomonas aeruginosa
    • Escalada, M. G., Harwood, J. L., Maillard, J. Y., and Ochs, D. (2005) Triclosan inhibition of fatty acid synthesis and its effect on growth of Escherichia coli and Pseudomonas aeruginosa J. Antimicrob. Chemother. 55, 879-882
    • (2005) J. Antimicrob. Chemother. , vol.55 , pp. 879-882
    • Escalada, M.G.1    Harwood, J.L.2    Maillard, J.Y.3    Ochs, D.4
  • 57
    • 0028128604 scopus 로고
    • Interactions of anti-inflammatory 2-arylpropionates (profens) with the metabolism of fatty acids: In vitro studies
    • Mayer, J. M., Roy-De Vos, M., Audergon, C., Testa, B., and Etter, J. C. (1994) Interactions of anti-inflammatory 2-arylpropionates (profens) with the metabolism of fatty acids: In vitro studies Int. J. Tissue React. 16, 59-72
    • (1994) Int. J. Tissue React. , vol.16 , pp. 59-72
    • Mayer, J.M.1    Roy-De Vos, M.2    Audergon, C.3    Testa, B.4    Etter, J.C.5
  • 58
    • 0029620688 scopus 로고
    • Metabolism of fenbufen by cultured 3T3-L1 adipocytes: Synthesis and metabolism of xenobiotic glycerolipids
    • Dodds, P. F., Chou, S. C., Ranasinghe, A., and Coleman, R. A. (1995) Metabolism of fenbufen by cultured 3T3-L1 adipocytes: synthesis and metabolism of xenobiotic glycerolipids J. Lipid Res. 36, 2493-2503
    • (1995) J. Lipid Res. , vol.36 , pp. 2493-2503
    • Dodds, P.F.1    Chou, S.C.2    Ranasinghe, A.3    Coleman, R.A.4
  • 59
    • 79959410970 scopus 로고    scopus 로고
    • Chiral inversion of 2-arylpropionyl-CoA esters by human alpha-methylacyl-CoA racemase 1A (P504S)-A potential mechanism for the anti-cancer effects of ibuprofen
    • Woodman, T. J., Wood, P. J., Thompson, A. S., Hutchings, T. J., Steel, G. R., Jiao, P., Threadgill, M. D., and Lloyd, M. D. (2011) Chiral inversion of 2-arylpropionyl-CoA esters by human alpha-methylacyl-CoA racemase 1A (P504S)-a potential mechanism for the anti-cancer effects of ibuprofen Chem. Commun. (Cambridge, U.K.) 47, 7332-7334
    • (2011) Chem. Commun. (Cambridge, U.K.) , vol.47 , pp. 7332-7334
    • Woodman, T.J.1    Wood, P.J.2    Thompson, A.S.3    Hutchings, T.J.4    Steel, G.R.5    Jiao, P.6    Threadgill, M.D.7    Lloyd, M.D.8
  • 60
    • 40349098747 scopus 로고    scopus 로고
    • Alpha-methylacyl-CoA racemase-An 'obscure' metabolic enzyme takes centre stage
    • Lloyd, M. D., Darley, D. J., Wierzbicki, A. S., and Threadgill, M. D. (2008) Alpha-methylacyl-CoA racemase-an 'obscure' metabolic enzyme takes centre stage FEBS J. 275, 1089-1102
    • (2008) FEBS J. , vol.275 , pp. 1089-1102
    • Lloyd, M.D.1    Darley, D.J.2    Wierzbicki, A.S.3    Threadgill, M.D.4
  • 61
    • 83955162185 scopus 로고    scopus 로고
    • Study on the metabolic mechanism of chiral inversion of S-mandelic acid in vitro
    • Gao, L. B., Wang, J. Z., Yao, T. W., and Zeng, S. (2012) Study on the metabolic mechanism of chiral inversion of S-mandelic acid in vitro Chirality 24, 86-95
    • (2012) Chirality , vol.24 , pp. 86-95
    • Gao, L.B.1    Wang, J.Z.2    Yao, T.W.3    Zeng, S.4
  • 62
    • 67651171546 scopus 로고    scopus 로고
    • Children's toxicology from bench to bed-Liver injury (1): Drug-induced metabolic disturbance-Toxicity of 5-FU for pyrimidine metabolic disorders and pivalic acid for carnitine metabolism
    • Ito, T. (2009) Children's toxicology from bench to bed-liver injury (1): Drug-induced metabolic disturbance-toxicity of 5-FU for pyrimidine metabolic disorders and pivalic acid for carnitine metabolism J. Toxicol. Sci. 34, SP217-SP222
    • (2009) J. Toxicol. Sci. , vol.34
    • Ito, T.1
  • 63
    • 0023475402 scopus 로고
    • Pivampicillin-promoted excretion of pivaloylcarnitine in humans
    • Melegh, B., Kerner, J., and Bieber, L. L. (1987) Pivampicillin-promoted excretion of pivaloylcarnitine in humans Biochem. Pharmacol. 36, 3405-3409
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 3405-3409
    • Melegh, B.1    Kerner, J.2    Bieber, L.L.3
  • 64
    • 0022891180 scopus 로고
    • Serum carnitine during valproic acid therapy
    • Laub, M. C., Paetzke-Brunner, I., and Jaeger, G. (1986) Serum carnitine during valproic acid therapy Epilepsia 27, 559-562
    • (1986) Epilepsia , vol.27 , pp. 559-562
    • Laub, M.C.1    Paetzke-Brunner, I.2    Jaeger, G.3
  • 65
    • 0022549245 scopus 로고
    • The role of carnitine in the conjugation of acidic xenobiotics
    • Quistad, G. B., Staiger, L. E., and Schooley, D. A. (1986) The role of carnitine in the conjugation of acidic xenobiotics Drug Metab. Dispos. 14, 521-525
    • (1986) Drug Metab. Dispos. , vol.14 , pp. 521-525
    • Quistad, G.B.1    Staiger, L.E.2    Schooley, D.A.3
  • 68
    • 0030447091 scopus 로고    scopus 로고
    • Nonsteroidal antiinflammatory drugs and uncoupling of mitochondrial oxidative phosphorylation
    • Mahmud, T., Rafi, S. S., Scott, D. L., Wrigglesworth, J. M., and Bjarnason, I. (1996) Nonsteroidal antiinflammatory drugs and uncoupling of mitochondrial oxidative phosphorylation Arthritis Rheum. 39, 1998-2003
    • (1996) Arthritis Rheum. , vol.39 , pp. 1998-2003
    • Mahmud, T.1    Rafi, S.S.2    Scott, D.L.3    Wrigglesworth, J.M.4    Bjarnason, I.5
  • 69
    • 0018938695 scopus 로고
    • Transport of protons across membranes by weak acids
    • McLaughlin, S. G. and Dilger, J. P. (1980) Transport of protons across membranes by weak acids Physiol. Rev. 60, 825-863
    • (1980) Physiol. Rev. , vol.60 , pp. 825-863
    • McLaughlin, S.G.1    Dilger, J.P.2
  • 70
    • 0037652327 scopus 로고    scopus 로고
    • Nonsteroidal antiinflammatory drugs and a selective cyclooxygenase 2 inhibitor uncouple mitochondria in intact cells
    • Krause, M. M., Brand, M. D., Krauss, S., Meisel, C., Vergin, H., Burmester, G. R., and Buttgereit, F. (2003) Nonsteroidal antiinflammatory drugs and a selective cyclooxygenase 2 inhibitor uncouple mitochondria in intact cells Arthritis Rheum. 48, 1438-1444
    • (2003) Arthritis Rheum. , vol.48 , pp. 1438-1444
    • Krause, M.M.1    Brand, M.D.2    Krauss, S.3    Meisel, C.4    Vergin, H.5    Burmester, G.R.6    Buttgereit, F.7
  • 73
    • 0033004051 scopus 로고    scopus 로고
    • Stereoselective and substrate-dependent inhibition of hepatic mitochondrial β-oxidation and oxidative phosphorylation by the non-steroidal anti inflammatory drugs ibuprofen, flurbiprofen, and ketorolac
    • Browne, G. S., Nelson, C., Nguyen, T., Ellis, B. A., Day, R. O., and Williams, K. M. (1999) Stereoselective and substrate-dependent inhibition of hepatic mitochondrial β-oxidation and oxidative phosphorylation by the non-steroidal anti inflammatory drugs ibuprofen, flurbiprofen, and ketorolac Biochem. Pharmacol. 57, 837-844
    • (1999) Biochem. Pharmacol. , vol.57 , pp. 837-844
    • Browne, G.S.1    Nelson, C.2    Nguyen, T.3    Ellis, B.A.4    Day, R.O.5    Williams, K.M.6
  • 74
    • 79251483520 scopus 로고    scopus 로고
    • CYP4F enzymes are responsible for the elimination of fingolimod (FTY720), a novel treatment of relapsing multiple sclerosis
    • Jin, Y., Zollinger, M., Borell, H., Zimmerlin, A., and Patten, C. J. (2011) CYP4F enzymes are responsible for the elimination of fingolimod (FTY720), a novel treatment of relapsing multiple sclerosis Drug Metab. Dispos. 39, 191-198
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 191-198
    • Jin, Y.1    Zollinger, M.2    Borell, H.3    Zimmerlin, A.4    Patten, C.J.5
  • 75
    • 84866331511 scopus 로고    scopus 로고
    • In vitro evaluation of major in vivo drug metabolic pathways using primary human hepatocytes and HepaRG cells in suspension and a dynamic three-dimensional bioreactor system
    • Darnell, M., Ulvestad, M., Ellis, E., Weidolf, L., and Andersson, T. B. (2012) In vitro evaluation of major in vivo drug metabolic pathways using primary human hepatocytes and HepaRG cells in suspension and a dynamic three-dimensional bioreactor system J. Pharmacol. Exp. Ther. 343, 134-144
    • (2012) J. Pharmacol. Exp. Ther. , vol.343 , pp. 134-144
    • Darnell, M.1    Ulvestad, M.2    Ellis, E.3    Weidolf, L.4    Andersson, T.B.5
  • 76
    • 84872712319 scopus 로고    scopus 로고
    • Metabolism and pharmacokinetics of 3-n-butylphthalide (NBP) in humans: The role of cytochrome P450s and alcohol dehydrogenase in biotransformation
    • Diao, X., Deng, P., Xie, C., Li, X., Zhong, D., Zhang, Y., and Chen, X. (2013) Metabolism and pharmacokinetics of 3-n-butylphthalide (NBP) in humans: the role of cytochrome P450s and alcohol dehydrogenase in biotransformation Drug Metab. Dispos. 41, 430-444
    • (2013) Drug Metab. Dispos. , vol.41 , pp. 430-444
    • Diao, X.1    Deng, P.2    Xie, C.3    Li, X.4    Zhong, D.5    Zhang, Y.6    Chen, X.7
  • 77
    • 54349093845 scopus 로고    scopus 로고
    • Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism
    • Fer, M., Corcos, L., Dréano, Y., Plée-Gautier, E., Salaün, J. P., Berthou, F., and Amet, Y. (2008) Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism J. Lipid Res. 49, 2379-2389
    • (2008) J. Lipid Res. , vol.49 , pp. 2379-2389
    • Fer, M.1    Corcos, L.2    Dréano, Y.3    Plée-Gautier, E.4    Salaün, J.P.5    Berthou, F.6    Amet, Y.7
  • 79
    • 62249155473 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from nonhepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction
    • Bauman, J. N., Kelly, J. M., Tripathy, S., Zhao, S. X., Lam, W. W., Kalgutkar, A. S., and Obach, R. S. (2009) Can in vitro metabolism-dependent covalent binding data distinguish hepatotoxic from nonhepatotoxic drugs? An analysis using human hepatocytes and liver S-9 fraction Chem. Res. Toxicol. 22, 332-340
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 332-340
    • Bauman, J.N.1    Kelly, J.M.2    Tripathy, S.3    Zhao, S.X.4    Lam, W.W.5    Kalgutkar, A.S.6    Obach, R.S.7
  • 81
    • 0032464529 scopus 로고    scopus 로고
    • Structural requirements for the hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes
    • Masubuchi, Y., Saito, H., and Horie, T. (1998) Structural requirements for the hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes J. Pharmacol. Exp. Ther. 287, 208-213
    • (1998) J. Pharmacol. Exp. Ther. , vol.287 , pp. 208-213
    • Masubuchi, Y.1    Saito, H.2    Horie, T.3
  • 84
    • 84866596506 scopus 로고    scopus 로고
    • Prediction of liver injury induced by chemicals in human with a multiparametric assay on isolated mouse liver mitochondria
    • Porceddu, M., Buron, N., Roussel, C., Labbe, G., Fromenty, B., and Borgne-Sanchez, A. (2012) Prediction of liver injury induced by chemicals in human with a multiparametric assay on isolated mouse liver mitochondria Toxicol. Sci. 129, 332-345
    • (2012) Toxicol. Sci. , vol.129 , pp. 332-345
    • Porceddu, M.1    Buron, N.2    Roussel, C.3    Labbe, G.4    Fromenty, B.5    Borgne-Sanchez, A.6
  • 85
    • 33947204690 scopus 로고    scopus 로고
    • Mitochondrial abnormalities-A link to idiosyncratic drug hepatotoxicity?
    • Boelsterli, U. A. and Lim, P. L. K. (2007) Mitochondrial abnormalities-A link to idiosyncratic drug hepatotoxicity? Toxicol. Appl. Pharmacol. 220, 92-107
    • (2007) Toxicol. Appl. Pharmacol. , vol.220 , pp. 92-107
    • Boelsterli, U.A.1    Lim, P.L.K.2
  • 86
    • 84857307490 scopus 로고    scopus 로고
    • The primary role of hepatic metabolism in idiosyncratic drug-induced liver injury
    • Amacher, D. E. (2012) The primary role of hepatic metabolism in idiosyncratic drug-induced liver injury Expert Opin. Drug Metab. Toxicol. 8, 335-347
    • (2012) Expert Opin. Drug Metab. Toxicol. , vol.8 , pp. 335-347
    • Amacher, D.E.1
  • 87
    • 84866598263 scopus 로고    scopus 로고
    • Palmitate increases the susceptibility of cells to drug-induced toxicity: An in vitro method to identify drugs with potential contraindications in patients with metabolic disease
    • Luo, Y., Rana, P., and Will, Y. (2012) Palmitate increases the susceptibility of cells to drug-induced toxicity: An in vitro method to identify drugs with potential contraindications in patients with metabolic disease Toxicol. Sci. 129, 346-362
    • (2012) Toxicol. Sci. , vol.129 , pp. 346-362
    • Luo, Y.1    Rana, P.2    Will, Y.3
  • 88
    • 46449089949 scopus 로고    scopus 로고
    • Evaluation of HepaRG cells as an in vitro model for human drug metabolism studies
    • Kanebratt, K. P. and Andersson, T. B. (2008) Evaluation of HepaRG cells as an in vitro model for human drug metabolism studies Drug Metab. Dispos. 36, 1444-1452
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 1444-1452
    • Kanebratt, K.P.1    Andersson, T.B.2
  • 89
    • 0035349906 scopus 로고    scopus 로고
    • The genetics and pathology of oxidative phosphorylation
    • Smeitink, J., van den Heuvel, L., and DiMauro, S. (2001) The genetics and pathology of oxidative phosphorylation Nat. Rev. Genet. 2, 342-352
    • (2001) Nat. Rev. Genet. , vol.2 , pp. 342-352
    • Smeitink, J.1    Van Den Heuvel, L.2    Dimauro, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.