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Chemical Compound Review

Depamide     2-propylpentanamide

Synonyms: Valpramide, Valpromida, Valpromide, Valpromidum, Depamide (TN), ...
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Disease relevance of alpha-Propylvaleramide


Psychiatry related information on alpha-Propylvaleramide


High impact information on alpha-Propylvaleramide

  • In contrast, valpromide, an analogue of VPA that does not induce histone acetylation, does not induce demethylation or expression of CMV-GFP [5].
  • The VPA derivative N-methyl-2,2,3,3,-tetramethyl-cyclopropane carboxamide reduces MIP synthase activity and has an affect similar to that of VPA on rat neurons, whereas another VPA derivative, valpromide, poorly affects the activity and has no affect on neurons [6].
  • The log metabolic ratio detected pronounced inhibition of epoxide hydrolase by valpromide (six subjects; median ratio, 0.91) and induction by phenobarbital/phenytoin (six subjects; median ratio, 2.42) [7].
  • Valpromide (KI = 5 mumol/L) was 100 times more potent than valproic acid (KI = 550 mumol/L) as an inhibitor of carbamazepine epoxide hydrolysis in microsomes [8].
  • Compared with valproic acid. valpromide has a very short half-life (mean +/- SD: 0.84 +/- 0.33h; n = 6), a high clearance value (70 +/- 31 L/h) and a large volume of distribution (75 +/- 13L) [9].

Chemical compound and disease context of alpha-Propylvaleramide

  • Whereas plasma peak levels and signs of central nervous system depression occur within a few hours after the acute ingestion of regular-release forms of valproate sodium, delayed toxicity and time to peak levels following valpromide ingestion can be seen as shown by the three reported cases [3].

Biological context of alpha-Propylvaleramide


Anatomical context of alpha-Propylvaleramide

  • Valpromide (0.5-2.0 mM) did not increase histone acetylation or P-gp expression in rat livers, but induced CYP3A expression.Conclusions:Valproic acid increased P-gp expression and function in human tumour cell lines and in rat liver [13].

Associations of alpha-Propylvaleramide with other chemical compounds


Gene context of alpha-Propylvaleramide


Analytical, diagnostic and therapeutic context of alpha-Propylvaleramide


  1. Lupus-like syndrome and vasculitis induced by valpromide. Bonnet, F., Morlat, P., De Witte, S., Combe, C., Beylot, J. J. Rheumatol. (2003) [Pubmed]
  2. In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy. Lindekens, H., Smolders, I., Khan, G.M., Bialer, M., Ebinger, G., Michotte, Y. Pharm. Res. (2000) [Pubmed]
  3. Delayed toxicity following acute ingestion of valpromide. Payen, C., Frantz, P., Martin, O., Parant, F., Moulsma, M., Pulce, C., Descotes, J. Human & experimental toxicology. (2004) [Pubmed]
  4. Valpromide increases amplitude of heart rate circadian rhythm in remitted bipolar and unipolar disorders. A placebo-controlled study. Lemoine, P., Fondarai, J., Faivre, T. Eur. Psychiatry (2000) [Pubmed]
  5. Valproate induces replication-independent active DNA demethylation. Detich, N., Bovenzi, V., Szyf, M. J. Biol. Chem. (2003) [Pubmed]
  6. Valproate decreases inositol biosynthesis. Shaltiel, G., Shamir, A., Shapiro, J., Ding, D., Dalton, E., Bialer, M., Harwood, A.J., Belmaker, R.H., Greenberg, M.L., Agam, G. Biol. Psychiatry (2004) [Pubmed]
  7. Measurement of in vivo microsomal epoxide hydrolase activity in white subjects. Kroetz, D.L., Kerr, B.M., McFarland, L.V., Loiseau, P., Wilensky, A.J., Levy, R.H. Clin. Pharmacol. Ther. (1993) [Pubmed]
  8. Inhibition of human liver microsomal epoxide hydrolase by valproate and valpromide: in vitro/in vivo correlation. Kerr, B.M., Rettie, A.E., Eddy, A.C., Loiseau, P., Guyot, M., Wilensky, A.J., Levy, R.H. Clin. Pharmacol. Ther. (1989) [Pubmed]
  9. Clinical pharmacology of valpromide. Bialer, M. Clinical pharmacokinetics. (1991) [Pubmed]
  10. Increased dipropylacetic acid bioavailability from dipropylacetamide by food. Pisani, F., D'Agostino, A.A., Fazio, A., Oteri, G., Primerano, G., Di Perri, R. Epilepsia (1982) [Pubmed]
  11. Sodium valproate and valpromide: differential interactions with carbamazepine in epileptic patients. Pisani, F., Fazio, A., Oteri, G., Ruello, C., Gitto, C., Russo, F., Perucca, E. Epilepsia (1986) [Pubmed]
  12. Stereoselective pharmacokinetic analysis and antiepileptic activity of N-2-hydroxypropyl valpromide, a central nervous system--active chiral valproylamide. Wasserman, M., Yagen, B., Blotnik, S., Papo, N., Bialer, M. Therapeutic drug monitoring. (2001) [Pubmed]
  13. The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Eyal, S., Lamb, J.G., Smith-Yockman, M., Yagen, B., Fibach, E., Altschuler, Y., White, H.S., Bialer, M. Br. J. Pharmacol. (2006) [Pubmed]
  14. Interaction of valproic acid and some analogues with microsomal epoxide hydrolase. Robbins, D.K., Wedlund, P.J., Elsberg, S., Oesch, F., Thomas, H. Biochem. Pharmacol. (1992) [Pubmed]
  15. Structure-pharmacokinetic relationships in a series of short fatty acid amides that possess anticonvulsant activity. Haj-Yehia, A., Bialer, M. Journal of pharmaceutical sciences. (1990) [Pubmed]
  16. Saccharomyces cerevisiae: an alternative source for human microsomal liver enzymes and its use in drug interaction studies. Eugster, H.P., Sengstag, C. Toxicology (1993) [Pubmed]
  17. Valpromide is a poor inhibitor of the cytosolic epoxide hydrolase. Pacifici, G.M., Temellini, A., Giuliani, L., Rane, A., Thomas, H., Oesch, F. Arch. Toxicol. (1989) [Pubmed]
  18. Pharmacokinetics of valpromide in dogs after various modes of administration. Bialer, M., Rubinstein, A. Biopharmaceutics & drug disposition. (1984) [Pubmed]
  19. The disposition of valpromide in rats and the isolated perfused rat liver. Billig, H., Ziv, E., Bar-On, H., Bialer, M. Drug Metab. Dispos. (1990) [Pubmed]
  20. Depamide: a preliminary report on its therapeutic efficacy in epilepsy. Musolino, R., Gallitto, G., Morgante, L., Pisani, F., Nisticò, G., Di Perri, R. Monographs in neural sciences. (1980) [Pubmed]
  21. Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy. Isoherranen, N., White, H.S., Klein, B.D., Roeder, M., Woodhead, J.H., Schurig, V., Yagen, B., Bialer, M. Pharm. Res. (2003) [Pubmed]
  22. Pharmacokinetics of valpromide after oral administration of a solution and a tablet to healthy volunteers. Bialer, M., Rubinstein, A., Raz, I., Abramsky, O. Eur. J. Clin. Pharmacol. (1984) [Pubmed]
  23. EEG and anticonvulsant effects of dipropylacetic acid and dipropylacetamide in the baboon Papio papio. Ehlers, C.L., Mulbry, L.W., Killam, E.K. Electroencephalography and clinical neurophysiology. (1980) [Pubmed]
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