Valproic acid

Valproate

Clinical data
Trade names	Convulex, Depakote, Epilim, Stavzor, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682412
License data	US FDA: Valproic+acid
Pregnancy category	AU: D US: X (Contraindicated) - for control of conditions other than severe epilepsy not amenable to other drugs
Routes of administration	By mouth, intravenous
ATC code	N03AG01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	Rapid absorption
Protein binding	80–90%
Metabolism	Hepatic—glucuronide conjugation 30–50%, mitochondrial β-oxidation over 40%
Biological half-life	9–16 hours
Excretion	Urine (30-50%)
Identifiers
IUPAC name 2-propylpentanoic acid
Synonyms	2-Propylvaleric acid
CAS Number	99-66-1 Y
PubChem CID	3121
DrugBank	DB00313 Y
ChemSpider	3009 Y
UNII	614OI1Z5WI
KEGG	D00399 Y
ChEBI	CHEBI:39867 Y
ChEMBL	CHEMBL109 Y
NIAID ChemDB	057177
ECHA InfoCard	100.002.525
Chemical and physical data
Formula	C8H16O2
Molar mass	144.211 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)C(CCC)CCC
InChI InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) Y Key:NIJJYAXOARWZEE-UHFFFAOYSA-N Y

Sodium valproate

Identifiers
IUPAC name sodium 2-propylpentanoate
CAS Number	1069-66-5 Y
ChemSpider	13428 Y
UNII	5VOM6GYJ0D
KEGG	D00710 Y
ChEBI	CHEBI:9925 Y
ChEMBL	CHEMBL433 Y
ECHA InfoCard	100.002.525
Chemical and physical data
Formula	C8H15NaO2
Molar mass	166.20 g·mol−1
3D model (Jmol)	Interactive image
SMILES [Na+].[O-]C(=O)C(CCC)CCC
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 Y Key:AEQFSUDEHCCHBT-UHFFFAOYSA-M Y

Valproate (VPA), and its valproic acid, sodium valproate, and divalproex sodium forms, are medications 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 and short acting formulations exist.

Common side effects include nausea, vomiting, sleepiness, and a dry mouth. Serious side effects can include liver problems and regular monitoring of liver function tests is therefore recommended. Other serious risks include pancreatitis and an increased suicide risk. It is known to cause serious abnormalities in the baby if taken during pregnancy. Because of this it is not typically recommended in women of childbearing age who have migraines. It is unclear how valproate works.

Valproate was first made in 1881 and came into medical use in 1962. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.14 and 0.52 USD per day. In the United States it costs about 0.90 USD per day. It is marketed under the brand name Depakote among others.

Valproic acid (VPA) is an organic weak acid. The conjugate base is valproate. The sodium salt of the acid is sodium valproate and a coordination complex of the two is known as divalproex sodium.