Metabolic activation of carboxylic acids

Bibliography

• Paulson SK, Hribar JD, Liu NW, et al. Metabolism and excretion of [(14)C]celecoxib in healthy male volunteers. Drug Metab Dispos 2000;28:308-14
   PubMed Web of Science ®Google Scholar
• Bakke OM, Manocchia M, de Abajo F, et al. Drug safety discontinuations in the United Kingdom, the United States, and Spain from 1974 through 1993: a regulatory perspective. Clin Pharmacol Ther 1995;58:108-17
   PubMed Web of Science ®Google Scholar
• Fung M, Thornton A, Mybeck K, et al. Evaluation of the characteristics of safety withdrawals of prescription drugs from worldwide pharmaceutical markets, 1960 to 1999. Drug Info J 2001;35:293-317
   Web of Science ®Google Scholar
• Zimmerman HJ. Update of hepatotoxicity due to classes of drugs in common clinical use: non-steroidal drugs, anti-inflammatory drugs, antibiotics, antihypertensives, and cardiac and psychotropic agents. Semin Liver Dis 1990;10:322-38
   PubMed Web of Science ®Google Scholar
• Zimmerman HJ. Hepatic injury associated with nonsteroidal anti-inflammatory drugs. In: Lewis AJ, Gay GR, editors, Nonsteroidal anti-inflammatory drugs: mechanisms and clinical uses. 2nd edition. New York: Marcel Dekker; 1994. p. 17194
   Google Scholar
• Bailey MJ, Dickinson RG. Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 2003;145:117-37
   PubMed Web of Science ®Google Scholar
• Levy DB, Vasilomanolakis EC. Anaphylactic reaction due to zomepirac. Drug Intell Clin Pharm 1984;18:983-4
   PubMedGoogle Scholar
• Gibson GG, Skett P. Enzymology and molecular mechanisms of drug metabolism reactions. In: Introduction to drug metabolism. 3rd edition. Cheltenham, UK: Nelson Thornes; 2001. p. 3784
   Google Scholar
• Ritter JK. Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 2000;129:171-93
   PubMed Web of Science ®Google Scholar
• Knights KM. Role of hepatic fatty acid:coenzyme A ligases in the metabolism of xenobiotic carboxylic acids. Clin Exp Pharmacol Physiol 1998;25:776-82
   PubMed Web of Science ®Google Scholar
• Knights KM, Sykes MJ, Miners JO. Amino acid conjugation: contribution to the metabolism and toxicity of xenobiotic carboxylic acids. Expert Opin Drug Metab Toxicol 2007;3:159-68
   PubMed Web of Science ®Google Scholar
• Olsen J, Bjornsdottir I, Hansen SH. Identification of coenzyme A-related tolmetin metabolites in rats: relationship with reactive drug metabolites. Xenobiotica 2003;33:561-70
   PubMed Web of Science ®Google Scholar
• Olsen J, Li C, Skonberg C, et al. Studies on the metabolism of tolmetin to the chemically reactive acyl-coenzyme A thioester intermediate in rats. Drug Metab Dispos 2007;35:758-64
   PubMed Web of Science ®Google Scholar
• Olsen J, Li C, Bjornsdottir I, et al. In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats. Chem Res Toxicol 2005;18:1729-36
   PubMed Web of Science ®Google Scholar
• Li C, Grillo MP, Benet LZ. In vivo mechanistic studies on the metabolic activation of 2-phenylpropionic Acid in rat. J Pharmacol Exp Ther 2003;305:250-6
   PubMed Web of Science ®Google Scholar
• Li C, Olurinde MO, Hodges LM, et al. Covalent binding of 2-phenylpropionyl-S-acyl-CoA thioester to tissue proteins in vitro. Drug Metab Dispos 2003;31:727-30
   PubMed Web of Science ®Google Scholar
• Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev 2002;54:589-98
   PubMed Web of Science ®Google Scholar
• Melegh B, Kerner J, Jaszai V, et al. Differential excretion of xenobiotic acyl-esters of carnitine due to administration of pivampicillin and valproate. Biochem Med Metab Biol 1990;43:30-8
   PubMedGoogle Scholar
• Mizojiri K, Futaguchi S, Norikura R, et al. Disposition of S-1108, a new oral cephem antibiotic, and metabolic fate of pivalic acid liberated from [pivaloyl-14C]S-1108 in rats and dogs. Antimicrob Agents Chemother 1995;39:1445-53
   PubMed Web of Science ®Google Scholar
• Muro H, Tatsuhara T, Sugimoto T, et al. Determination of urinary valproylcarnitine by gas chromatography-mass spectrometry with selected-ion monitoring. J Chromatogr B Biomed Appl 1995;663:83-9
   PubMedGoogle Scholar
• Tatsuhara T, Muro H, Matsuda Y, et al. Determination of valproic acid and its metabolites by gas chromatography-mass spectrometry with selected ion monitoring. J Chromatogr 1987;399:183-95
   PubMed Web of Science ®Google Scholar
• Hutt AJ, Caldwell J. Amino acid conjugation. In: Mulder GJ, editor, Conjugation reactions in drug metabolism. 1st edition. London, UK: Taylor & Francis; 1990. p. 273304
   Google Scholar
• Hall SD, Quan X. The role of coenzyme A in the biotransformation of 2-arylpropionic acids. Chem Biol Interact 1994;90:235-51
   PubMed Web of Science ®Google Scholar
• Wsol V, Skalova L, Szotakova B. Chiral inversion of drugs: coincidence or principle? Curr Drug Metab 2004;5:517-33
   PubMed Web of Science ®Google Scholar
• DeLeve LD, Kaplowitz N. Glutathione metabolism and its role in hepatotoxicity. Pharmacol Ther 1991;52:287-305
   PubMed Web of Science ®Google Scholar
• Grillo MP, Benet LZ. Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro. Drug Metab Dispos 2002;30:55-62
   PubMed Web of Science ®Google Scholar
• Shore LJ, Fenselau C, King AR, et al. Characterization and formation of the glutathione conjugate of clofibric acid. Drug Metab Dispos 1995;23:119-23
   PubMed Web of Science ®Google Scholar
• Li C, Benet LZ, Grillo MP. Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes. Chem Res Toxicol 2002;15:1480-7
   PubMed Web of Science ®Google Scholar
• Shirley MA, Guan X, Kaiser DG, et al. Taurine conjugation of ibuprofen in humans and in rat liver in vitro Relationship to metabolic chiral inversion. J Pharmacol Exp Ther 1994;269:1166-75
   PubMed Web of Science ®Google Scholar
• Grillo MP, Hua F. Identification of zomepirac-s-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile. Drug Metab Dispos 2003;31:1429-36
   PubMed Web of Science ®Google Scholar
• McDonagh AF, Palma LA, Lauff JJ, et al. Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest 1984;74:763-70
   PubMed Web of Science ®Google Scholar
• van Breemen RB, Fenselau C. Acylation of albumin by 1-O-acyl glucuronides. Drug Metab Dispos 1985;13:318-20
   PubMed Web of Science ®Google Scholar
• Drew R, Knights K. Postulated reactive intermediates of NSAIDs. Agents Actions Suppl 1985;17:127-33
   PubMedGoogle Scholar
• Smith PC, McDonagh AF, Benet LZ. Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest 1986;77:934-9
   PubMed Web of Science ®Google Scholar
• Stogniew M, Fenselau C. Electrophilic reactions of acyl-linked glucuronides: formation of clofibrate mercapturate in humans. Drug Metab Dispos 1982;10:609-13
   PubMed Web of Science ®Google Scholar
• Hyneck ML, Smith PC, Munafo A, et al. Disposition and irreversible plasma protein binding of tolmetin in humans. Clin Pharmacol Ther 1988;44:107-14
   PubMed Web of Science ®Google Scholar
• Benet LZ, Spahn-Langguth H, Iwakawa S, et al. Predictability of the covalent binding of acidic drugs in man. Life Sci 1993;53:L141-6
   PubMedGoogle Scholar
• Bolze S, Bromet N, Gay-Feutry C, et al. Development of an in vitro screening model for the biosynthesis of acyl glucuronide metabolites and the assessment of their reactivity toward human serum albumin. Drug Metab Dispos 2002;30:404-13
   PubMed Web of Science ®Google Scholar
• Wang J, Davis M, Li F, et al. A novel approach for predicting acyl glucuronide reactivity via Schiff base formation: development of rapidly formed peptide adducts for LC/MS/MS measurements. Chem Res Toxicol 2004;17:1206-16
   PubMed Web of Science ®Google Scholar
• Tishler SL, Goldman P. Properties and reactions of salicyl-coenzyme A. Biochem Pharmacol 1970;19:143-50
   PubMed Web of Science ®Google Scholar
• Watt JA, Dickinson RG. Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions. Biochem Pharmacol 1990;39:1067-75
   PubMed Web of Science ®Google Scholar
• Corcoran O, Mortensen RW, Hansen SH, et al. HPLC/1H NMR spectroscopic studies of the reactive alpha-1-O-acyl isomer formed during acyl migration of S-naproxen beta-1-O-acyl glucuronide. Chem Res Toxicol 2001;14:1363-70
   PubMed Web of Science ®Google Scholar
• Mortensen RW, Corcoran O, Cornett C, et al. S-naproxen-beta-1-O-acyl glucuronide degradation kinetic studies by stopped-flow high-performance liquid chromatography-1H NMR and high-performance liquid chromatography-UV. Drug Metab Dispos 2001;29:375-80
   PubMed Web of Science ®Google Scholar
• Mortensen RW, Sidelmann UG, Tjornelund J, et al. Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide. Chirality 2002;14:305-12
   PubMed Web of Science ®Google Scholar
• Rachmel A, Hazelton GA, Yergey AL, et al. Furosemide 1-O-acyl glucuronide: in vitro biosynthesis and pH-dependent isomerization to beta-glucuronidase-resistant forms. Drug Metab Dispos 1985;13:705-10
   PubMed Web of Science ®Google Scholar
• Hasegawa J, Smith PC, Benet LZ. Apparent intramolecular acyl migration of zomepirac glucuronide. Drug Metab Dispos 1982;10:469-73
   PubMed Web of Science ®Google Scholar
• Bailey MJ, Dickinson RG. Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. Chem Res Toxicol 1996;9:659-66
   PubMed Web of Science ®Google Scholar
• Williams AM, Worrall S, de Jersey J, et al. Studies on the reactivity of acyl glucuronides-III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans. Biochem Pharmacol 1992;43:745-55
   PubMed Web of Science ®Google Scholar
• Sidelmann U, Hansen SH, Gavaghan C, et al. Development of a simple liquid chromatographic method for the separation of mixtures of positional isomers and anomers of synthetic 2-, 3- and 4-fluorobenzoic acid glucuronides formed via acyl migration reactions. J Chromatogr B Biomed Appl 1996;685:113-22
   PubMedGoogle Scholar
• Ding A, Ojingwa JC, McDonagh AF, et al. Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc Natl Acad Sci USA 1993;90:3797-801
   PubMed Web of Science ®Google Scholar
• Ding A, Ziaamirhosseini P, McDonagh AF, et al. Reactivity of tolmetin glucuronide with human serum-albumin: identification of binding-sites and mechanisms of reaction by tandem mass-spectrometry. Drug Metab Dispos 1995;23:369-76
   PubMed Web of Science ®Google Scholar
• Dickinson RG, King AR. Studies on the reactivity of acyl glucuronides: II. Interaction of diflunisal acyl glucuronide and its isomers with human serum albumin in vitro. Biochem Pharmacol 1991;42:2301-6
   PubMed Web of Science ®Google Scholar
• Smith PC, Benet LZ, McDonagh AF. Covalent binding of zomepirac glucuronide to proteins: evidence for a Schiff base mechanism. Drug Metab Dispos 1990;18:639-44
   PubMed Web of Science ®Google Scholar
• Y, Burlingame AL, Benet LZ. Mechanisms for covalent binding of benoxaprofen glucuronide to human serum albumin: studies by tandem mass spectrometry. Drug Metab Dispos 1998;26:246-56
   PubMed Web of Science ®Google Scholar
• Kretz-Rommel A, Boelsterli UA. Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos 1994;22:956-61
   PubMed Web of Science ®Google Scholar
• Bradow G, Kan LS, Fenselau C. Studies of intramolecular rearrangements of acyl-linked glucuronides using salicylic acid, flufenamic acid, and (S)- and (R)-benoxaprofen and confirmation of isomerization in acyl-linked delta 9-11-carboxytetrahydrocannabinol glucuronide. Chem Res Toxicol 1989;2:316-24
   PubMed Web of Science ®Google Scholar
• Ebner T, Heinzel G, Prox A, et al. Disposition and chemical stability of telmisartan 1-O-acylglucuronide. Drug Metab Dispos 1999;27:1143-9
   PubMed Web of Science ®Google Scholar
• Hyneck ML, Munafo A, Benet LZ. Effect of pH on acyl migration and hydrolysis of tolmetin glucuronide. Drug Metab Dispos 1988;16:322-4
   PubMed Web of Science ®Google Scholar
• Vanderhoeven SJ, Lindon JC, Troke J, et al. NMR and QSAR studies on the transacylation reactivity of model 1beta-O-acyl glucuronides. I. Design, synthesis and degradation rate measurement. Xenobiotica 2004;34:73-85
   PubMed Web of Science ®Google Scholar
• Williams AM, Dickinson RG. Studies on the reactivity of acyl glucuronidesVI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem Pharmacol 1994;47:457-67
   PubMed Web of Science ®Google Scholar
• Sallustio BC, Nunthasomboon S, Drogemuller CJ, et al. In vitro covalent binding of nafenopin-CoA to human liver proteins. Toxicol Appl Pharmacol 2000;163:176-82
   PubMed Web of Science ®Google Scholar
• Sidenius U, Skonberg C, Olsen J, et al. In vitro reactivity of carboxylic acid-CoA thioesters with glutathione. Chem Res Toxicol 2004;17:75-81
   PubMed Web of Science ®Google Scholar
• Olsen J, Bjornsdottir I, Tjornelund J, et al. Chemical reactivity of the naproxen acyl glucuronide and the naproxen coenzyme A thioester towards bionucleophiles. J Pharm Biomed Anal 2002;29:7-15
   PubMed Web of Science ®Google Scholar
• Li C, Benet LZ, Grillo MP. Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites. Chem Res Toxicol 2002;15:1309-17
   PubMed Web of Science ®Google Scholar
• Grillo MP, Knutson CG, Sanders PE, et al. Studies on the chemical reactivity of diclofenac acyl glucuronide with lutathione: identification of diclofenac-S-acyl-glutathione in rat bile. Drug Metab Dispos 2003;31:1327-36
   PubMed Web of Science ®Google Scholar
• Li C, Grillo MP, Benet LZ. In vitro studies on the chemical reactivity of 2,4-dichlorophenoxyacetyl-S-acyl-CoA thioester. Toxicol Appl Pharmacol 2003;187:101-9
   PubMed Web of Science ®Google Scholar
• Hargus SJ, Amouzedeh HR, Pumford NR, et al. Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem Res Toxicol 1994;7:575-82
   PubMed Web of Science ®Google Scholar
• Olsen J, Bjornsdottir I, Tjornelund J, et al. Identification of the amino acids of human serum albumin involved in the reaction with the naproxen acyl coenzyme A thioester using liquid chromatography combined with fluorescence and mass spectrometric detection. Anal Biochem 2003;312:148-56
   PubMed Web of Science ®Google Scholar
• Bakke OM, Wardell WM, Lasagna L. Drug discontinuations in the United Kingdom and the United States, 1964 to 1983: issues of safety. Clin Pharmacol Ther 1984;35:559-67
   PubMed Web of Science ®Google Scholar
• Hart FD, Boardman PL. Ibufenac (4-isobutylphenyl acetic acid). Ann Rheum Dis 1965;24:61-5
   PubMed Web of Science ®Google Scholar
• Zimmerman, HJ. Drug-induced hepatic disease. In: Plaa GL, Hewitt WR, editors, Toxicology of the liver. 2nd edition. Washington, DC: Taylor & Francis; 1997.p. 360
   Google Scholar
• Chatfield DH, Green JN. Disposition and metabolism of benoxaprofen in laboratory animals and man. Xenobiotica 1978;8:133-44
   PubMed Web of Science ®Google Scholar
• Dong JQ, Liu J, Smith PC. Role of benoxaprofen and flunoxaprofen acyl glucuronides in covalent binding to rat plasma and liver proteins in vivo. Biochem Pharmacol 2005;70:937-48
   PubMed Web of Science ®Google Scholar
• Ayrton AD, Ioannides C, Parke DV. Induction of the cytochrome-P450 I-family and Iv-family and peroxisomal proliferation in the liver of rats treated with benoxaprofen possible implications in its hepatotoxicity. Biochem Pharmacol 1991;42:109-15
   PubMed Web of Science ®Google Scholar
• Banks AT, Zimmerman HJ, Ishak KG, et al. Diclofenac-associated hepatotoxicity: analysis of 180 cases reported to the Food and Drug Administration as adverse reactions. Hepatology 1995;22:820-7
   PubMed Web of Science ®Google Scholar
• Greaves RR, Agarwal A, Patch D, et al. Inadvertent diclofenac rechallenge from generic and non-generic prescribing, leading to liver transplantation for fulminant liver failure. Eur J Gastroenterol Hepatol 2001;13:71-3
   PubMed Web of Science ®Google Scholar
• Kretz-Rommel A, Boelsterli UA. Cytotoxic activity of T cells and non-T cells from diclofenac-immunized mice against cultured syngeneic hepatocytes exposed to diclofenac. Hepatology 1995;22:213-22
   PubMed Web of Science ®Google Scholar
• Bougie D, Johnson ST, Weitekamp LA, et al. Sensitivity to a metabolite of diclofenac as a cause of acute immune hemolytic anemia. Blood 1997;90:407-13
   PubMed Web of Science ®Google Scholar
• Kretz-Rommel A, Boelsterli UA. Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol Appl Pharmacol 1993;120:155-61
   PubMed Web of Science ®Google Scholar
• Kretz-Rommel A, Boelsterli UA. Selective protein adducts to membrane proteins in cultured rat hepatocytes exposed to diclofenac: radiochemical and immunochemical analysis. Mol Pharmacol 1994;45:237-44
   PubMed Web of Science ®Google Scholar
• Hargus SJ, Martin BM, George JW, et al. Covalent modification of rat liver dipeptidyl peptidase IV (CD26) by the nonsteroidal anti-inflammatory drug diclofenac. Chem Res Toxicol 1995;8:993-6
   PubMed Web of Science ®Google Scholar
• Seitz S, Kretz-Rommel A, Oude Elferink RP, et al. Selective protein adduct formation of diclofenac glucuronide is critically dependent on the rat canalicular conjugate export pump (Mrp2). Chem Res Toxicol 1998;11:513-9
   PubMed Web of Science ®Google Scholar
• Wang M, Gorrell MD, McGaughan GW, et al. Dipeptidyl peptidase IV is a target for covalent adduct formation with the acyl glucuronide metabolite of the anti-inflammatory drug zomepirac. Life Sci 2001;68:785-97
   PubMed Web of Science ®Google Scholar
• Wang M, Gorrell MD, Abbott CA, et al. Hepatic covalent adduct formation with zomepirac in the CD26-deficient mouse. J Gastroenterol Hepatol 2002;17:66-71
   PubMed Web of Science ®Google Scholar
• Boelsterli UA. Diclofenac-induced liver injury: a paradigm of idiosyncratic drug toxicity. Toxicol Appl Pharmacol 2003;192:307-22
   PubMed Web of Science ®Google Scholar
• Masubuchi Y, Nakayama S, Horie T. Role of mitochondrial permeability transition in diclofenac-induced hepatocyte injury in rats. Hepatology 2002;35:544-51
   PubMed Web of Science ®Google Scholar
• Mingatto FE, Santos AC, Uyemura SA, et al. In vitro interaction of nonsteroidal anti-inflammatory drugs on oxidative phosphorylation of rat kidney mitochondria: respiration and ATP synthesis. Arch Biochem Biophys 1996;334:303-8
   PubMed Web of Science ®Google Scholar
• Masubuchi Y, Yamada S, Horie T. Possible mechanism of hepatocyte injury induced by diphenylamine and its structurally related nonsteroidal anti-inflammatory drugs. J Pharmacol Exp Ther 2000;292:982-7
   PubMed Web of Science ®Google Scholar
• Hertz R, Bar-Tana J. The acylation of proteins by xenobiotic amphipathic carboxylic acids in cultured rat hepatocytes. Biochem J 1988;254:39-44
   PubMed Web of Science ®Google Scholar
• Dodds PF, Chou SC, Ranasinghe A, et al. Metabolism of fenbufen by cultured 3T3-L1 adipocytes: synthesis and metabolism of xenobiotic glycerolipids. J Lipid Res 1995;36:2493-503
   PubMed Web of Science ®Google Scholar
• Moorhouse KG, Dodds PF, Hutson DH. Xenobiotic triacylglycerol formation in isolated hepatocytes. Biochem Pharmacol 1991;41:1179-85
   PubMed Web of Science ®Google Scholar
• Williams K, Day R, Knihinicki R, et al. The stereoselective uptake of ibuprofen enantiomers into adipose tissue. Biochem Pharmacol 1986;35:3403-5
   PubMed Web of Science ®Google Scholar
• Dodds PF. Xenobiotic lipids: the inclusion of xenobiotic compounds in pathways of lipid biosynthesis. Prog Lipid Res 1995;34:219-47
   PubMed Web of Science ®Google Scholar
• Fromenty B, Pessayre D. Inhibition of mitochondrial beta-oxidation as a mechanism of hepatotoxicity. Pharmacol Ther 1995;67:101-54
   PubMed Web of Science ®Google Scholar
• Deschamps D, Fisch C, Fromenty B, et al. Inhibition by salicylic acid of the activation and thus oxidation of long chain fatty acids. Possible role in the development of Reye's syndrome. J Pharmacol Exp Ther 1991;259:894-904
   PubMed Web of Science ®Google Scholar
• Bjorge SM, Baillie TA. Inhibition of medium-chain fatty acid beta-oxidation in vitro by valproic acid and its unsaturated metabolite, 2-n-propyl-4-pentenoic acid. Biochem Biophys Res Commun 1985;132:245-52
   PubMed Web of Science ®Google Scholar
• Silva MF, Ruiter JP, Ijlst L, et al. Synthesis and intramitochondrial levels of valproyl-coenzyme A metabolites. Anal Biochem 2001;290:60-7
   PubMed Web of Science ®Google Scholar
• Silva MF, Ijlst L, Allers P, et al. Valproyl-dephosphoCoA: a novel metabolite of valproate formed in vitro in rat liver mitochondria. Drug Metab Dispos 2004;32:1304-10
   PubMed Web of Science ®Google Scholar
• Stanley H, Sherratt A, Osmundsen H. On the mechanisms of some pharmacological actions of the hypoglycaemic toxins hypoglycin and pent-4-enoic acid. A way out of the present confusion. Biochem Pharmacol 1976;25:743-50
   PubMed Web of Science ®Google Scholar
• Wenz A, Thorpe C, Ghisla S. Inactivation of general acyl-CoA dehydrogenase from pig kidney by a metabolite of hypoglycin A. J Biol Chem 1981;256:9809-12
   PubMed Web of Science ®Google Scholar
• Lieu YK, Hsu BY, Price WA, et al. Carnitine effects on coenzyme A profiles in rat liver with hypoglycin inhibition of multiple dehydrogenases. Am J Physiol 1997;272:E359-66
   PubMed Web of Science ®Google Scholar
• Kassahun K, Hu P, Grillo MP, et al. Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes. Chem Biol Interact 1994;90:253-75
   PubMed Web of Science ®Google Scholar
• Tang W, Borel AG, Fujimiya T, et al. Fluorinated analogs as mechanistic probes in valproic acid hepatotoxicity: hepatic microvesicular steatosis and glutathione status. Chem Res Toxicol 1995;8:671-82
   PubMed Web of Science ®Google Scholar
• Grillo MP, Chiellini G, Tonelli M, et al. Effect of alpha-fluorination of valproic acid on valproyl-S-acyl-CoA formation in vivo in rats. Drug Metab Dispos 2001;29:1210-5
   PubMed Web of Science ®Google Scholar
• Gillette JR. Commentary. A perspective on the role of chemically reactive metabolites of foreign compounds in toxicity. I. Correlation of changes in covalent binding of reactivity metabolites with changes in the incidence and severity of toxicity. Biochem Pharmacol 1974;23:2785-94
   PubMed Web of Science ®Google Scholar
• Olsen J. Reactive drug metabolites: formation, metabolism and reactivity of acyl coenzyme A thioesters in vitro and in vivo. PhD thesis, Department of Analytical and Pharmaceutical Chemistry, Royal Danish School of Pharmacy, Copenhagen; 2002
   Google Scholar
• Boelsterli UA, Zimmerman HJ, Kretz-Rommel A. Idiosyncratic liver toxicity of nonsteroidal antiinflammatory drugs: molecular mechanisms and pathology. Crit Rev Toxicol 1995;25:207-35
   PubMed Web of Science ®Google Scholar
• Rabinovitz M, Van Thiel DH. Hepatotoxicity of nonsteroidal anti-inflammatory drugs. Am J Gastroenterol 1992;87:1696-704
   PubMed Web of Science ®Google Scholar
• Von Holt C, Chang J, von Holt M, et al. Metabolism and metabolic effects of hypoglycin. Biochim Biophys Acta 1964;90:611-3
   PubMed Web of Science ®Google Scholar