Valproic Acid
Title: Valproic Acid
CAS Registry Number: 99-66-1
CAS Name: 2-Propylpentanoic acid
Additional Names: 2-propylvaleric acid; di-n-propylacetic acid
Trademarks: Convulex (Pharmacia); Depakene (Abbott)
Molecular Formula: C8H16O2
Molecular Weight: 144.21
Percent Composition: C 66.63%, H 11.18%, O 22.19%
Literature References: Antiepileptic; increases levels of g-aminobutyric acid (GABA) in the brain. Prepn: B. S. Burton, Am. Chem. J. 3, 385 (1882); E. Oberreit, Ber. 29, 1998 (1896); M. Tiffeneau, Y. Deux, Compte Rend. 212, 105 (1941). Anticonvulsant activity: H. Meunier et al., Therapie 18, 435 (1963). Toxicity data: Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). Comprehensive description: Z. L. Chang, Anal. Profiles Drug Subs. 8, 529-556 (1979). Review of teratogenicity studies: H. Nau et al., Pharmacol. Toxicol. 69, 310-321 (1991); R. Alsdorf, D. F. Wyszynski, Expert Opin. Drug Safety 4, 345-353 (2005). Review of pharmacology and clinical experience in epilepsy: E. M. Rimmer, A. Richens, Pharmacotherapy 5, 171-184 (1985); in psychiatric disease: D. R. P. Guay, ibid. 15, 631-647 (1995); in migraine prophylaxis: C. E. Shelton, J. F. Connelly, Ann. Pharmacother. 30, 865-866 (1996). Review of pharmacodynamics and mechanisms of action: W. Löscher, Prog. Neurobiol. 58, 31-59 (1999).
Properties: Colorless liquid with characteristic odor. bp 219.5°. nD24.5 1.425. d40 0.9215. pKa 4.6. Very sol in organic solvents. Soly in water: 1.3 mg/ml. LD50 orally in rats: 670 mg/kg (Jenner).
Boiling point: bp 219.5°
pKa: pKa 4.6
Index of refraction: nD24.5 1.425
Density: d40 0.9215
Toxicity data: LD50 orally in rats: 670 mg/kg (Jenner)
 
Derivative Type: Sodium salt (1:1)
CAS Registry Number: 1069-66-5
Additional Names: Sodium valproate
Trademarks: Depacon (Abbott); Depakin (Sanofi-Synthelabo); Dépakine (Sanofi-Aventis); Epilim (Sanofi-Aventis); Ergenyl (Sanofi-Synthelabo); Leptilan (Dolorgiet); Orfiril (Desitin)
Molecular Formula: C8H15NaO2
Molecular Weight: 166.19
Percent Composition: C 57.82%, H 9.10%, Na 13.83%, O 19.25%
Properties: White, odorless, crystalline, deliquescent powder. pKa 4.8. Hygroscopic. One gram is sol in 0.4 ml water; 1.5 ml ethanol; 5 ml methanol. Practically insol in common organic solvents. LD50 orally in mice: 1700 mg/kg (Meunier).
pKa: pKa 4.8
Toxicity data: LD50 orally in mice: 1700 mg/kg (Meunier)
 
Derivative Type: Sodium salt (2:1)
CAS Registry Number: 76584-70-8
Additional Names: Sodium hydrogen bis(2-propylpentanoate); divalproex sodium; valproate semisodium
Manufacturers' Codes: Abbott 50711
Trademarks: Depakote (Abbott); Valcote (Abbott)
Molecular Formula: C16H31NaO4
Molecular Weight: 310.40
Percent Composition: C 61.91%, H 10.07%, Na 7.41%, O 20.62%
 
Derivative Type: Magnesium salt
Trademarks: Depamag (Sigma-Tau)
Molecular Formula: C16H30MgO4
Molecular Weight: 310.71
Percent Composition: C 61.85%, H 9.73%, Mg 7.82%, O 20.60%
 
Therap-Cat: Anticonvulsant; antimanic; antimigraine.
Keywords: Anticonvulsant; Antimigraine; Antimanic.

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