Effect of α-fluorination of valproic acid on valproyl-S-acyl-CoA formation in vivo in rats

Drug Metabolism and Disposition

Volumn 29, Issue 9, 2001, Pages 1210-1215

  Grillo, M P ^a   Chiellini, G ^a   Tonelli, M ^a   Benet, L Z ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; FATTY ACID; THIOESTER; VALPROIC ACID; VALPROIC ACID DERIVATIVE;

ANIMAL TISSUE; ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER; LIVER TOXICITY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; RAT;

ACYL COENZYME A; ANIMALS; FLUORINE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIVER; MALE; RATS; RATS, SPRAGUE-DAWLEY; VALPROIC ACID;

EID: 0034876276     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Chemical and immunological comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma
2. Metabolism of valproate to hepatotoxic intermediates
3. Influence of valproic acid on hepatic carbohydrate and lipid metabolism
4. o glycoprotein and a synthetic peptide containing the palmitoylation site are both autoacylated
5. Inhibition of medium-chain fatty acid β-oxidation in vitro by valproic acid and its unsaturated metabolite, 2-n-propyl-4-pentenoic acid
6. Overview of coenzyme A metabolism and its role in cellular toxicity
7. Xenobiotic acyl-coenzymes A: Critical intermediates in the biochemical pharmacology and toxicology of carboxylic acids
8. Species variation in the taurine conjugation of clofibric acid
9. Carnitine deficiency: A possible mechanism for valproate hepatotoxicity
10. Disposition of valproic acid in the rat: Dose-dependent metabolism, distribution, enterohepatic recirculation and choleretic effect
11. Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs
12. The acylation of proteins by xenobiotic amphipathic carboxylic acids in cultured rat hepatocytes
13. In vivo formation of the thiol conjugates of reactive metabolites of 4-ene VPA and its analog 4-pentenoic acid
14. Identification and characterization of the glutathione and N-acetyl-cysteine conjugates of (E)-2-propyl-2,4-pentadienoic acid, a toxic metabolite of valproic acid, in rats and humans
15. Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes
16. The hepatotoxicity of valproic acid and its metabolites in rats. I. Toxicological, biochemical and histopathological studies
17. Lack of evidence for perfluorodecanoylor perfluorooctanoyl-coenzyme A formation in male and female rats
18. Valproate-induced hepatic steatogenisis in rats
19. Effects of valproate and E-2-en valproate on functional and morphological parameters of rat liver. II. Influence of phenobarbital comedication
20. Covalent and noncovalent interactions in acute lethal cell injury caused by chemicals
21. The covalent binding to protein of valproic acid and its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid, in rats and in isolated rat hepatocytes
22. In vitro covalent binding of nafenopin-CoA to human liver proteins
23. Mitochondrial β-oxidation
24. Alpha-fluoro-acid and alpha-fluoro amide analogs of acetyl-CoA as inhibitors of citrate synthase: Effect of pKa matching on binding affinity and hydrogen bond length
25. Valproate (VPA) metabolites in various clinical conditions of probable VPA-associated hepatotoxicity
26. D, L-alpha-fluoropalmitic acid inhibits sphingosine base formation and accumulates in membrane lipids of cultured mammalian cells
27. Preparation and assay of acyl coenzyme A and other thiol esters: Use of hydroxylamine
28. A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its α-fluorinated analogue: Phase II metabolism and pharmacokinetics
29. Time course of α-fluorinated valproic acid in mouse brain and serum and its effect on synaptosomal γ-aminobutyric acid levels in comparison with valproic acid
30. The reductive half-reaction in the acyl-CoA dehydrogenases
31. A single therapeutic dose of valproate affects liver carbohydrate, fat, adenylate, amino acid, coenzyme A, and carnitine metabolism in infant mice: Possible clinical significance
32. Properties and reactions of salicyl-coenzyme A
33. Fluorinated acids and esters
34. Valproate-induced hepatic injury: Analysis of 23 fatal cases