Valproic Acid, Sodium Salt

• CAT Number: A000892
• CAS Number: 1069-66-5
• Molecular Formula: C₈H₁₅O₂.Na
• Molecular Weight: 166.19
• Purity: ≥95%
• Target: HDAC
• Solubility: >8.4mg/mL in DMSO
• Storage: 3 years -20C powder
• InChI: InChI=1S/C8H16O2.Na/c1-3-5-7(6-4-2)8(9)10;/h7H,3-6H2,1-2H3,(H,9,10);/q;+1/p-1
• InChIKey: AEQFSUDEHCCHBT-UHFFFAOYSA-M
• SMILES: CCCC(CCC)C(=O)[O-].[Na+]

Valproate (VPA), also known valproic acid, sodium valproate, and divalproex sodium, is a medication primarily used to treat epilepsy and bipolar disorder and to prevent migraine headaches. It is useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. It can be given intravenously or by mouth. Long acting formulations exist. Valproic acid dissociates to the valproate ion in the gastrointestinal tract. The mechanisms by which valproate exerts its antiepileptic effects have not been established. It has been suggested that its activity in epilepsy is related to increased brain concentrations of gamma-aminobutyric acid (GABA).

Reference

1: Tomson T, Marson A, Boon P, Canevini MP, Covanis A, Gaily E, Kälviäinen R, Trinka E. Valproate in the treatment of epilepsy in girls and women of childbearing potential. Epilepsia. 2015 Jul;56(7):1006-19. doi: 10.1111/epi.13021. Epub 2015 May 16. Review. PubMed PMID: 25851171.2: Yang CS, Zhang LL, Lin YZ, Guo Q. Sodium valproate for the treatment of Tourette׳s syndrome in children: a systematic review and meta-analysis. Psychiatry Res. 2015 Apr 30;226(2-3):411-7. doi: 10.1016/j.psychres.2014.08.058. Epub 2014 Oct 2. Review. PubMed PMID: 25724485.3: Dueñas-Gonzalez A, Coronel J, Cetina L, González-Fierro A, Chavez-Blanco A, Taja-Chayeb L. Hydralazine-valproate: a repositioned drug combination for the epigenetic therapy of cancer. Expert Opin Drug Metab Toxicol. 2014 Oct;10(10):1433-44. doi: 10.1517/17425255.2014.947263. Epub 2014 Aug 25. Review. PubMed PMID: 25154405.4: Trinka E, Höfler J, Zerbs A, Brigo F. Efficacy and safety of intravenous valproate for status epilepticus: a systematic review. CNS Drugs. 2014 Jul;28(7):623-39. doi: 10.1007/s40263-014-0167-1. Review. PubMed PMID: 24806973; PubMed Central PMCID: PMC4078236.5: Cipriani A, Reid K, Young AH, Macritchie K, Geddes J. Valproic acid, valproate and divalproex in the maintenance treatment of bipolar disorder. Cochrane Database Syst Rev. 2013 Oct 17;10:CD003196. doi: 10.1002/14651858.CD003196.pub2. Review. PubMed PMID: 24132760.6: Rigamonti A, Lauria G, Grimod G, Bianchi G, Salmaggi A. Valproate induced hyperammonemic encephalopathy successfully treated with levocarnitine. J Clin Neurosci. 2014 Apr;21(4):690-1. doi: 10.1016/j.jocn.2013.04.033. Epub 2013 Oct 8. Review. PubMed PMID: 24119342.7: Brigo F, Igwe SC, Nardone R, Tezzon F, Bongiovanni LG, Trinka E. A common reference-based indirect comparison meta-analysis of intravenous valproate versus intravenous phenobarbitone for convulsive status epilepticus. Epileptic Disord. 2013 Sep;15(3):314-23. doi: 10.1684/epd.2013.0601. Review. PubMed PMID: 23981687.8: Nolan SJ, Marson AG, Pulman J, Tudur Smith C. Phenytoin versus valproate monotherapy for partial onset seizures and generalised onset tonic-clonic seizures. Cochrane Database Syst Rev. 2013 Aug 23;8:CD001769. doi: 10.1002/14651858.CD001769.pub2. Review. PubMed PMID: 23970302.9: Linde M, Mulleners WM, Chronicle EP, McCrory DC. Valproate (valproic acid or sodium valproate or a combination of the two) for the prophylaxis of episodic migraine in adults. Cochrane Database Syst Rev. 2013 Jun 24;6:CD010611. doi: 10.1002/14651858.CD010611. Review. PubMed PMID: 23797677.10: Linde M, Mulleners WM, Chronicle EP, McCrory DC. Antiepileptics other than gabapentin, pregabalin, topiramate, and valproate for the prophylaxis of episodic migraine in adults. Cochrane Database Syst Rev. 2013 Jun 24;6:CD010608. doi: 10.1002/14651858.CD010608. Review. PubMed PMID: 23797674.11: Knights MJ, Finlay E. The effects of sodium valproate on the renal function of children with epilepsy. Pediatr Nephrol. 2014 Jul;29(7):1131-8. doi: 10.1007/s00467-013-2512-x. Epub 2013 May 30. Review. PubMed PMID: 23720013.12: Chan E, McQueen F. Valproate-induced hyperammonaemia superimposed upon severe neuropsychiatric lupus: a case report and review of the literature. Clin Rheumatol. 2013 Mar;32(3):403-7. doi: 10.1007/s10067-012-2150-x. Epub 2012 Dec 28. Review. PubMed PMID: 23271612.13: Lewis C, Deshpande A, Tesar GE, Dale R. Valproate-induced hyperammonemic encephalopathy: a brief review. Curr Med Res Opin. 2012 Jun;28(6):1039-42. doi: 10.1185/03007995.2012.694362. Epub 2012 Jun 6. Review. PubMed PMID: 22587482.14: Liu X, Wu Y, Chen Z, Ma M, Su L. A systematic review of randomized controlled trials on the theraputic effect of intravenous sodium valproate in status epilepticus. Int J Neurosci. 2012 Jun;122(6):277-83. doi: 10.3109/00207454.2012.657376. Epub 2012 Feb 23. Review. PubMed PMID: 22248033.15: Brigo F, Storti M, Del Felice A, Fiaschi A, Bongiovanni LG. IV Valproate in generalized convulsive status epilepticus: a systematic review. Eur J Neurol. 2012 Sep;19(9):1180-91. doi: 10.1111/j.1468-1331.2011.03606.x. Epub 2011 Dec 19. Review. PubMed PMID: 22182304.16: Martikainen MH, Roine S. Rapid improvement of a complex migrainous episode with sodium valproate in a patient with CADASIL. J Headache Pain. 2012 Jan;13(1):95-7. doi: 10.1007/s10194-011-0400-y. Epub 2011 Nov 8. Review. PubMed PMID: 22065121; PubMed Central PMCID: PMC3253158.17: Wang ZF, Fessler EB, Chuang DM. Beneficial effects of mood stabilizers lithium, valproate and lamotrigine in experimental stroke models. Acta Pharmacol Sin. 2011 Dec;32(12):1433-45. doi: 10.1038/aps.2011.140. Epub 2011 Nov 7. Review. PubMed PMID: 22056617; PubMed Central PMCID: PMC4010202.18: Gill D, Derry S, Wiffen PJ, Moore RA. Valproic acid and sodium valproate for neuropathic pain and fibromyalgia in adults. Cochrane Database Syst Rev. 2011 Oct 5;(10):CD009183. doi: 10.1002/14651858.CD009183.pub2. Review. PubMed PMID: 21975791.19: Santivasi WL, Kulkarni S, Patton ML, Haith LR, Guilday RE, Reigart CL, Ackerman BH. Infiltration of sodium valproate with compartment syndrome and bullous reaction: case report and literature review. Burns. 2011 Nov;37(7):e59-62. doi: 10.1016/j.burns.2011.05.010. Epub 2011 Jun 28. Review. PubMed PMID: 21715098.20: Patel SM, Graff-Radford J, Wieland ML. Valproate-induced Fanconi syndrome in a 27-year-old woman. J Gen Intern Med. 2011 Sep;26(9):1072-4. doi: 10.1007/s11606-011-1708-7. Epub 2011 Apr 23. Review. PubMed PMID: 21516379; PubMed Central PMCID: PMC3157517.