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Chemical Compound Review

pivalicacid     2,2-dimethylpropanoic acid

Synonyms: Pivalinsaeure, Versatic 5, PubChem16826, Pivalic acid, acido pivalico, ...
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Disease relevance of NSC65449


High impact information on NSC65449


Chemical compound and disease context of NSC65449


Biological context of NSC65449

  • A comparison of the ocular disposition of the pivalic acid released by hydrolysis of dipivefrin and that of topically applied free pivalic acid showed that the released pivalic acid is not metabolized in the eye and is rapidly eliminated from the eye with no apparent sequestration in ocular tissues [7].
  • In this study, administration of pivalic acid or its sodium salt was found to decrease the L-carnitine concentration in the epididymal lumen of the hamster; it also tested whether this decrease affected sperm cell motility, chromatin structure, or fertilizing capacity [8].

Anatomical context of NSC65449


Associations of NSC65449 with other chemical compounds


Analytical, diagnostic and therapeutic context of NSC65449

  • Provision of pivalic acid or its sodium salt (20 mM or 40 mM) in the drinking water of mature male golden hamsters for 30 days reduced (by 72%, 75%, and 83% in three experiments) the L-carnitine concentration of the cauda epididymidis but did not inhibit sperm chromatin condensation, as assessed by flow cytometry [8].


  1. Possible mechanism for species difference on the toxicity of pivalic acid between dogs and rats. Yamaguchi, T., Nakajima, Y., Nakamura, Y. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  2. Pivalate-generating prodrugs and carnitine homeostasis in man. Brass, E.P. Pharmacol. Rev. (2002) [Pubmed]
  3. 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. Mizojiri, K., Futaguchi, S., Norikura, R., Katsuyama, Y., Nagasaki, T., Yoshimori, T., Nakanishi, M. Antimicrob. Agents Chemother. (1995) [Pubmed]
  4. Phase I clinical studies of S-1108: safety and pharmacokinetics in a multiple-administration study with special emphasis on the influence on carnitine body stores. Nakashima, M., Uematsu, T., Oguma, T., Yoshida, T., Mizojiri, K., Matsuno, S., Yamamoto, S. Antimicrob. Agents Chemother. (1992) [Pubmed]
  5. Enantioselective covalent binding of 2-phenylpropionic Acid to protein in vitro in rat hepatocytes. Li, C., Benet, L.Z., Grillo, M.P. Chem. Res. Toxicol. (2002) [Pubmed]
  6. Crystal forms of piroxicam pivalate: preparation and characterization of two polymorphs. Giordano, F., Gazzaniga, A., Moyano, J.R., Ventura, P., Zanol, M., Peveri, T., Carima, L. Journal of pharmaceutical sciences. (1998) [Pubmed]
  7. Comparison of ocular disposition of free pivalic acid and pivalic acid esterified in dipivefrin. Tamaru, R.D., Davis, W.L., Anderson, J.A. Arch. Ophthalmol. (1983) [Pubmed]
  8. Effects of pivalic acid and sodium pivalate on L-carnitine concentrations in the cauda epididymidis and on male fertility in the hamster. Lewin, L.M., Fournier-Delpech, S., Weissenberg, R., Golan, R., Cooper, T., Pholpramool, C., Shochat, L. Reprod. Fertil. Dev. (1997) [Pubmed]
  9. Cytotoxicity of pivalylphenylephrine and pivalic acid to corneal endothelium. Staatz, W.D., Edelhauser, H.F., Lehner, R., Van Horn, D.L. Arch. Ophthalmol. (1980) [Pubmed]
  10. Diagnosis of isovaleric acidaemia by tandem mass spectrometry: false positive result due to pivaloylcarnitine in a newborn screening programme. Abdenur, J.E., Chamoles, N.A., Guinle, A.E., Schenone, A.B., Fuertes, A.N. J. Inherit. Metab. Dis. (1998) [Pubmed]
  11. Evidence for tip velocity oscillations in dendritic solidification. LaCombe, J.C., Koss, M.B., Frei, J.E., Giummarra, C., Lupulescu, A.O., Glicksman, M.E. Physical review. E, Statistical, nonlinear, and soft matter physics . (2002) [Pubmed]
  12. Induction of peroxisomal beta-oxidation and P-450 4A-dependent activities by pivalic and trichloroacetic acid in rat liver and kidney. Zanelli, U., Puccini, P., Acerbi, D., Ventura, P., Gervasi, P.G. Arch. Toxicol. (1996) [Pubmed]
  13. Formation of pivaloylcarnitine in heart and brown adipose tissue in the rat. Diep, Q.N., Bøhmer, T., Skrede, S. Biochim. Biophys. Acta (1995) [Pubmed]
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