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Chemical Compound Review:

CHEMBL1367 2-propylpent-4-enoic acid

Synonyms: R,S-4-en-VPA, AG-E-06577, AC1L2XON, CTK4C9400, AR-1E5224, ...

Siemes, H. et al., Rettenmeier, A.W. et al., Rettie, A.E. et al., Levy, R.H. et al., Tang, W. et al., et al.

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Disease relevance of 2-Allylpentanoic acid

Increased values of 2-n-propyl-4-pentenoic acid metabolite of VPA (4-ene-VPA), could be detected only in 1 of the 5 patients with fulminant liver failure and in one other child with a slight hepatic dysfunction, indicating that this VPA metabolite is not the decisive hepatotoxin or indicator of hepatotoxicity [1].

High impact information on 2-Allylpentanoic acid

The cytochrome P-450-mediated desaturation of valproic acid (VPA) to its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid (4-ene-VPA), was examined in liver microsomes from rats, mice, rabbits and humans [2].
A minor valproic acid metabolite, 2-propyl-4-pentenoic acid (4-ene-VPA), formed by a cytochrome P450-mediated reaction, has been shown to be a potent inducer of microvesicular steatosis in rats [3].
A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its alpha-fluorinated analogue: phase II metabolism and pharmacokinetics [4].
Characterization of thiol-conjugated metabolites of 2-propylpent-4-enoic acid (4-ene VPA), a toxic metabolite of valproic acid, by electrospray tandem mass spectrometry [5].
Pharmacokinetics and enterohepatic circulation of 2-n-propyl-4-pentenoic acid in the rat [6].

Biological context of 2-Allylpentanoic acid

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 [7].

References

Valproate (VPA) metabolites in various clinical conditions of probable VPA-associated hepatotoxicity. Siemes, H., Nau, H., Schultze, K., Wittfoht, W., Drews, E., Penzien, J., Seidel, U. Epilepsia (1993) [Pubmed]
Cytochrome P-450-catalyzed desaturation of valproic acid in vitro. Species differences, induction effects, and mechanistic studies. Rettie, A.E., Boberg, M., Rettenmeier, A.W., Baillie, T.A. J. Biol. Chem. (1988) [Pubmed]
Effects of polytherapy with phenytoin, carbamazepine, and stiripentol on formation of 4-ene-valproate, a hepatotoxic metabolite of valproic acid. Levy, R.H., Rettenmeier, A.W., Anderson, G.D., Wilensky, A.J., Friel, P.N., Baillie, T.A., Acheampong, A., Tor, J., Guyot, M., Loiseau, P. Clin. Pharmacol. Ther. (1990) [Pubmed]
A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its alpha-fluorinated analogue: phase II metabolism and pharmacokinetics. Tang, W., Abbott, F.S. Drug Metab. Dispos. (1997) [Pubmed]
Characterization of thiol-conjugated metabolites of 2-propylpent-4-enoic acid (4-ene VPA), a toxic metabolite of valproic acid, by electrospray tandem mass spectrometry. Tang, W., Abbott, F.S. Journal of mass spectrometry : JMS. (1996) [Pubmed]
Pharmacokinetics and enterohepatic circulation of 2-n-propyl-4-pentenoic acid in the rat. Singh, K., Orr, J.M., Abbott, F.S. Drug Metab. Dispos. (1988) [Pubmed]
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. Rettenmeier, A.W., Prickett, K.S., Gordon, W.P., Bjorge, S.M., Chang, S.L., Levy, R.H., Baillie, T.A. Drug Metab. Dispos. (1985) [Pubmed]

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