Valproic acid metabolism and its effects on mitochondrial fatty acid oxidation: A review
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M. Duran | R. Wanders | R. Wanders | M. Durán | L. Ijlst | J. Ruiter | M. F. Silva | C. Aires | P. B. Luis | I. Tavares de Almeida | M. F. B. Silva | C. C. P. Aires | P. B. M. Luis | J. P. N. Ruiter | L. IJlst | R. J. A. Wanders | I. Tavares de Almeida | P. Luis | P. B. M. Luis
[1] T. Baillie,et al. Metabolic activation of unsaturated derivatives of valproic acid: role of microsomal versus mitochondrial enzyme systems , 1992 .
[2] T. Bohan,et al. Valproylcarnitine: a novel drug metabolite identified by fast atom bombardment and thermospray liquid chromatography-mass spectrometry. , 1985, Clinica chimica acta; international journal of clinical chemistry.
[3] D. Turnbull,et al. The effects of valproate on intermediary metabolism in isolated rat hepatocytes and intact rats. , 1983, Biochemical pharmacology.
[4] D. Cotariu,et al. Valproic acid and the liver. , 1988, Clinical chemistry.
[5] G. Zaccara,et al. Clinical Pharmacokinetics of Valproic Acid — 1988 , 1988, Clinical pharmacokinetics.
[6] W. Loscher,et al. Identification of Metabolites of Valproic Acid in Serum of Humans, Dog, Rat, and Mouse , 1978, Epilepsia.
[7] A. Bröer,et al. Functional and pharmacological characterization of human Na(+)-carnitine cotransporter hOCTN2. , 2000, American journal of physiology. Renal physiology.
[8] S. Kolvraa,et al. The occurrence of C6--C10-dicarboxylic acids in urine from patients and rats treated with dipropylacetate. , 1980, Biochemical medicine.
[9] J. de Jersey,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. , 1992, Biochemical pharmacology.
[10] W. Löscher,et al. Effect of metabolites of valproic acid on the metabolism of GABA in brain and brain nerve endings , 1981, Neuropharmacology.
[11] R. Wanders,et al. Synthesis and intramitochondrial levels of valproyl-coenzyme A metabolites. , 2001, Analytical biochemistry.
[12] H. Nau,et al. Valproic acid and its metabolites: placental transfer, neonatal pharmacokinetics, transfer via mother's milk and clinical status in neonates of epileptic mothers. , 1981, The Journal of pharmacology and experimental therapeutics.
[13] L. Benet,et al. Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? , 1992, Drug metabolism reviews.
[14] S. Servidei,et al. Late onset lipid storage myopathy due to multiple acyl CoA dehydrogenase deficiency triggered by valproate , 1991, Neuromuscular Disorders.
[15] M. Sztajnkrycer. Valproic Acid Toxicity: Overview and Management , 2002, Journal of toxicology. Clinical toxicology.
[16] K Farrell,et al. Identification and characterization of the glutathione and N-acetylcysteine conjugates of (E)-2-propyl-2,4-pentadienoic acid, a toxic metabolite of valproic acid, in rats and humans. , 1991, Drug metabolism and disposition: the biological fate of chemicals.
[17] M. Nagao,et al. Influence of valproic acid on the expression of various acyl‐CoA dehydrogenases in rats , 1999, Pediatrics international : official journal of the Japan Pediatric Society.
[18] R. Hehlmann,et al. Fatal Liver Failure Associated with Valproate Therapy in a Patient with Friedreich's Disease: Review of Valproate Hepatotoxicity in Adults , 1999, Epilepsia.
[19] H. Nau,et al. Binding of a valproate metabolite to the trifunctional protein of fatty acid oxidation , 1996, FEBS letters.
[20] F. Glocker,et al. Valproic acid triggers acute rhabdomyolysis in a patient with carnitine palmitoyltransferase type II deficiency , 2001, Neuromuscular Disorders.
[21] Robert A. Harris,et al. Influence of valproic acid on hepatic carbohydrate and lipid metabolism. , 1983, Archives of biochemistry and biophysics.
[22] K. Moore,et al. Hepatic hydrolysis of octanoyl-CoA and valproyl-CoA in control and valproate-fed animals. , 1988, The International journal of biochemistry.
[23] I. T. de Almeida,et al. Valproyl-dephosphoCoA: a novel metabolite of valproate formed in vitro in rat liver mitochondria. , 2004, Drug metabolism and disposition: the biological fate of chemicals.
[24] I. T. de Almeida,et al. Studies on the extra-mitochondrial CoA -ester formation of valproic and Delta4 -valproic acids. , 2007, Biochimica et biophysica acta.
[25] D. Shen,et al. Absorption, distribution, and excretion , 1999 .
[26] M. Leão. Valproate as a Cause of Hyperammonemia in Heterozygotes With ornithine-transcarbamylase Deficiency , 1995, Neurology.
[27] T. Bohan,et al. l‐Carnitine Supplementation in Childhood Epilepsy: Current Perspectives , 1998, Epilepsia.
[28] T. Bohan,et al. Effect of l-carnitine treatment for valproate-induced hepatotoxicity , 2001, Neurology.
[29] D. Pessayre,et al. Impaired mitochondrial function in microvesicular steatosis. Effects of drugs, ethanol, hormones and cytokines. , 1997, Journal of hepatology.
[30] N. Reynolds,et al. Human brain, plasma, and cerebrospinal fluid concentration of sodium valproate after 72 hours of therapy , 1981, Neurology.
[31] G. Carraz,et al. [Pharmacodynamic properties of N-dipropylacetic acid]. , 1963, Therapie.
[32] F. Abbott,et al. Chemistry and biotransformation , 1999 .
[33] I. Tein,et al. Reversal of valproic acid-associated impairment of carnitine uptake in cultured human skin fibroblasts. , 1994, Biochemical and biophysical research communications.
[34] M. Bailey,et al. Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. , 1996, Chemical research in toxicology.
[35] D. Pessayre,et al. Mitochondrial dysfunction in NASH: causes, consequences and possible means to prevent it. , 2006, Mitochondrion.
[36] M. Hjelm,et al. Evidence of inherited urea cycle defect in a case of fatal valproate toxicity. , 1986, British medical journal.
[37] S. Shorvon. Epidemiology, classification, natural history, and genetics of epilepsy , 1990, The Lancet.
[38] T. Baillie,et al. Biotransformation and pharmacokinetics in the rhesus monkey of 2-n-propyl-4-pentenoic acid, a toxic metabolite of valproic acid. , 1986, Drug metabolism and disposition: the biological fate of chemicals.
[39] T. Woolf. Handbook of Drug Metabolism , 1999 .
[40] G. Avanzini,et al. Clinical Pharmacokinetics of Antiepileptic Drugs in Paediatric Patients , 1995, Clinical pharmacokinetics.
[41] T. Kuhara,et al. Metabolism of branched medium chain length fatty acid. II--beta-oxidation of sodium dipropylacetate in rats. , 1974, Biomedical mass spectrometry.
[42] C. Stanley,et al. Relationship between unusual hepatic acyl coenzyme A profiles and the pathogenesis of Reye syndrome. , 1988, The Journal of clinical investigation.
[43] D. Pessayre,et al. Hepatotoxicity due to mitochondrial dysfunction , 2004, Cell Biology and Toxicology.
[44] W. Löscher. Basic Pharmacology of Valproate , 2002 .
[45] A. Munnich,et al. Valproate-induced hepatic failure in a case of cytochromec oxidase deficiency , 1994, European Journal of Pediatrics.
[46] Thomas K. H. Chang,et al. Oxidative Stress as a Mechanism of Valproic Acid-Associated Hepatotoxicity , 2006, Drug metabolism reviews.
[47] M. Gris,et al. Science review: Carnitine in the treatment of valproic acid-induced toxicity – what is the evidence? , 2005, Critical care.
[48] T. Baillie,et al. Studies on the metabolic fate of valproic acid in the rat using stable isotope techniques. , 1987, Xenobiotica; the fate of foreign compounds in biological systems.
[49] U. Stephani,et al. Severe Hepatotoxicity During Valproate Therapy: An Update and Report of Eight New Fatalities , 1994, Epilepsia.
[50] J. Nezu,et al. Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. , 1999, The Journal of pharmacology and experimental therapeutics.
[51] A. Kamiya,et al. Urinary metabolites of valproic acid in epileptic patients. , 1998, Biological & pharmaceutical bulletin.
[52] Paul B Watkins,et al. Drug‐induced liver injury: Summary of a single topic clinical research conference , 2006, Hepatology.
[53] C. Gau,et al. Interaction between Anticonvulsants and Human Placental Carnitine Transporter , 2004, Epilepsia.
[54] R. Gugler,et al. Clinical Pharmacokinetics of Valproic Acid , 1980, Clinical pharmacokinetics.
[55] F. Dreifuss,et al. Valproic acid hepatic fatalities. III. U.S. experience since 1986 , 1996, Neurology.
[56] J. Sarles,et al. Inappropriate liver transplantation in a child with Alpers–Huttenlocher syndrome misdiagnosed as valproate‐induced acute liver failure , 2000, Pediatric transplantation.
[57] N. Gerber,et al. Reye-like syndrome associated with valproic acid therapy. , 1979, The Journal of pediatrics.
[58] T. Baillie,et al. Effects of polytherapy with phenytoin, carbamazepine, and stiripentol on formation of 4‐ene‐valproate, a hepatotoxic metabolite of valproic acid , 1990, Clinical pharmacology and therapeutics.
[59] G. Donnan,et al. Human brain, plasma, and cerebrospinal fluid concentration of sodium valproate after 72 hours of therapy. , 1981, Neurology.
[60] Devane Cl. Pharmacokinetics, drug interactions, and tolerability of valproate. , 2003, Psychopharmacology bulletin.
[61] W. Löscher,et al. Valproic acid: brain and plasma levels of the drug and its metabolites, anticonvulsant effects and gamma-aminobutyric acid (GABA) metabolism in the mouse. , 1982, The Journal of pharmacology and experimental therapeutics.
[62] G. Granneman,et al. The Hepatotoxicity of Valproic Acid and Its Metabolites in Rats. II. Intermediary and Valproic Acid Metabolism , 1984, Hepatology.
[63] R. Wanders,et al. Complete beta-oxidation of valproate: cleavage of 3-oxovalproyl-CoA by a mitochondrial 3-oxoacyl-CoA thiolase. , 2002, The Biochemical journal.
[64] C. Nemeroff,et al. Pharmacology of valproate. , 2003, Psychopharmacology bulletin.
[65] J. Fong,et al. On the rate-determining step of fatty acid oxidation in heart. Inhibition of fatty acid oxidation by 4-pentenoic acid. , 1978, The Journal of biological chemistry.
[66] B. Burchell. Transformation Reactions: Glucuronidation , 1999 .
[67] A. Mato,et al. Valproic Acid for the Treatment of Myeloid Malignancies , 2008, Cancer.
[68] A. Sandor,et al. Inhibition of carnitine biosynthesis by valproic acid in rats--the biochemical mechanism of inhibition. , 1996, Biochemical pharmacology.
[69] K. Brouwer,et al. Hepatobiliary disposition of valproic acid and valproate glucuronide: Use of a pharmacokinetic model to examine the rate‐limiting steps and potential sites of drug interactions , 1996, Hepatology.
[70] H. Nau,et al. Valproic Acid and Metabolites: Pharmacological and Toxicological Studies , 1984, Epilepsia.
[71] R. Davis,et al. Valproic acid. A reappraisal of its pharmacological properties and clinical efficacy in epilepsy. , 1994, Drugs.
[72] I. T. de Almeida,et al. Differential effect of valproate and its Delta2- and Delta4-unsaturated metabolites, on the beta-oxidation rate of long-chain and medium-chain fatty acids. , 2001, Chemico-biological interactions.
[73] W. Dodson,et al. Chronic valproate administration reduces fasting ketonemia in children , 1983, Neurology.
[74] K. Farrell,et al. Identification and characterization of N-acetylcysteine conjugates of valproic acid in humans and animals. , 2000, Drug metabolism and disposition: the biological fate of chemicals.
[75] G. Kong,et al. Gene expression profiles of murine fatty liver induced by the administration of valproic acid. , 2007, Toxicology and applied pharmacology.
[76] J. Williams,et al. Mitochondrial myopathy, encephalopathy, lactic acidosis and stroke-like episodes (MELAS) triggered by valproate therapy , 1997, European Journal of Pediatrics.
[77] J. Raskind,et al. The Role of Carnitine Supplementation during Valproic Acid Therapy , 2000, The Annals of pharmacotherapy.
[78] S. Krähenbühl,et al. Mitochondrial diseases represent a risk factor for valproate-induced fulminant liver failure. , 2000, Liver.
[79] F. Chiarelli,et al. Valproate-Induced Hyperammonemic Encephalopathy , 2002, Metabolic Brain Disease.
[80] W. Hofmann,et al. Fatal Liver Failure in 16 Children with Valproate Therapy , 1988, Epilepsia.
[81] T. Baillie,et al. Studies on the biotransformation in the perfused rat liver of 2-n-propyl-4-pentenoic acid, a metabolite of the antiepileptic drug valproic acid. Evidence for the formation of chemically reactive intermediates. , 1985, Drug metabolism and disposition: the biological fate of chemicals.
[82] K. Ishak,et al. Valproate‐Induced Hepatic Injury: Analyses of 23 Fatal Cases , 2007, Hepatology.
[83] A. Evans,et al. Pharmacokinetics of L-Carnitine , 2003, Clinical pharmacokinetics.
[84] E. Perucca,et al. Pharmacological and Therapeutic Properties of Valproate , 2002, CNS drugs.
[85] T. Kuhara,et al. Metabolism of sodium dipropylacetate in human , 1978, European journal of drug metabolism and pharmacokinetics.
[86] D. Norwood,et al. Mitochondrial metabolism of valproic acid. , 1991, Biochemistry.
[87] F. Van hoof,et al. In vitro effects of valproate and valproate metabolites on mitochondrial oxidations. Relevance of CoA sequestration to the observed inhibitions. , 1992, Biochemical pharmacology.
[88] T. Baillie,et al. Studies on the beta-oxidation of valproic acid in rat liver mitochondrial preparations. , 1991, Drug metabolism and disposition: the biological fate of chemicals.
[89] G. Finocchiaro,et al. The enzymatic basis for the metabolism and inhibitory effects of valproic acid: dehydrogenation of valproyl-CoA by 2-methyl-branched-chain acyl-CoA dehydrogenase. , 1990, Biochimica et biophysica acta.
[90] W. Löscher. Basic pharmacology of valproate: a review after 35 years of clinical use for the treatment of epilepsy. , 2002, CNS drugs.
[91] M. Oechsner,et al. Hyperammonaemic encephalopathy after initiation of valproate therapy in unrecognised ornithine transcarbamylase deficiency , 1998, Journal of neurology, neurosurgery, and psychiatry.
[92] T. Baillie,et al. Cytochrome P-450--catalyzed formation of delta 4-VPA, a toxic metabolite of valproic acid. , 1987, Science.
[93] T. Baillie,et al. Metabolic activation of valproic acid and drug-mediated hepatotoxicity. Role of the terminal olefin, 2-n-propyl-4-pentenoic acid. , 1988, Chemical research in toxicology.
[94] G. Granneman,et al. The Hepatotoxicity of Valproic Acid and Its Metabolites in Rats. I. Toxicologic, Biochemical and Histopathologic Studies , 1984, Hepatology.
[95] W. Löscher. Pharmacological effects and mechanisms of action , 1999 .
[96] S. Russell. Carnitine as an antidote for acute valproate toxicity in children , 2007, Current opinion in pediatrics.
[97] H. Schulz,et al. The relationship between mitochondrial activation and toxicity of some substituted carboxylic acids. , 1994, Chemico-biological interactions.
[98] D. Schmidt. Adverse effects and interactions with other drugs , 1999 .
[99] T. Baillie,et al. Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes. , 1994, Chemico-biological interactions.
[100] I. T. de Almeida,et al. Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. , 2001, Clinical biochemistry.
[101] Thomas K. H. Chang,et al. Valproic acid I: time course of lipid peroxidation biomarkers, liver toxicity, and valproic acid metabolite levels in rats. , 2005, Toxicological sciences : an official journal of the Society of Toxicology.
[102] R. Wanders,et al. Progressive Infantile Neurodegeneration Caused by 2-Methyl-3-Hydroxybutyryl-CoA Dehydrogenase Deficiency: A Novel Inborn Error of Branched-Chain Fatty Acid and Isoleucine Metabolism , 2000, Pediatric Research.
[103] F. Dreifuss,et al. Valproic acid hepatic fatalities. , 1989, Neurology.
[104] A. Rettie,et al. Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene-valproic acid. , 1997, The Journal of pharmacology and experimental therapeutics.
[105] E. Longin,et al. Effects of Valproate on Acylcarnitines in Children with Epilepsy Using ESI‐MS/MS , 2007, Epilepsia.