File:2-propylpentanoic_acid_200.svg · Wikimedia Commons · See Wikimedia Commons
valproic acid
Sign in to saveAlso known as LEP321, A-44090, 2-n-propyl-n-valeric acid, n-DPA, DPA, dipropylacetic acid, VPA, 2-n-propyl-4-pentenoic acid
Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and as a mood stabilizer in the treatment of bipolar disorder. They are useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. They can be given intravenously or by mouth, and the tablet forms exist in both long- and short-acting formulations.
OverviewAI-generated
Valproic acid, also identified as 2-propylpentanoic acid, is a chemical compound with the formula C₈H₁₆O₂. It has a mass of 144.115 and a density of 0.904. The substance melts at 25 degrees and boils at 221.5 degrees. Its inception is recorded as 1967.
Chemical properties include a charge of 0, an xlogp of 2.8, and a tpsa of 37.3. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors. PubChem lists its weight as 144.21.
The compound is referenced by 1,979 other encyclopedia articles. A PubMed query for valproic acid yields a count of 19638.
Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.metabolism
- Liver—glucuronide conjugation 30–50%, mitochondrial β-oxidation over 40%
- Drug.elimination_half life
- 9–16 hours
- Drug.excretion
- Urine (30–50%)
- Drug.CAS_number
- 76584-70-8
- Drug.PubChem
- 23663956
- Drug.IUPHAR_ligand
- 7009
- Drug.DrugBank
- DBSALT000185
- Drug.ChemSpiderID
- 48337
- Drug.UNII
- 644VL95AO6
- Drug.KEGG
- D00304
- Drug.ChEBI
- 4667
- Drug.ChEMBL
- 2105613
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464404696
- Drug.image
- Sodium-valproate-2D-skeletal.png
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Valproato Sódico.png
via Wikipedia infobox
Chemical data
- Formula
- C8H16O2
- Molecular weight
- 144.21 g/mol
- IUPAC name
- 2-propylpentanoic acid
- SMILES
- CCCC(CCC)C(=O)O
- InChIKey
- NIJJYAXOARWZEE-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
19,638 papers- Valproic Acid in Women of Reproductive Potential: Panacea or Pandora's Box.Neurology India · 2025
- Versatile Valproic Acid.Issues in mental health nursing · 2022
- Valproic acid.Indian pediatrics · 1991
- The pharmacogenomics of valproic acid.Journal of human genetics · 2017
- Valproic acid toxicity: overview and management.Journal of toxicology. Clinical toxicology · 2002
via PubMed
Wikidata facts
- Mass
- 144.115
Show 10 more facts
- found in taxon
- Valeriana officinalis
- chemical formula
- C₈H₁₆O₂
- World Health Organisation international non-proprietary name
- valproic acid
- canonical SMILES
- CCCC(CCC)C(=O)O
- Commons category
- Valproic acid
- legal status (medicine)
- boxed warning
- inception
- 1967-00-00
- melting point
- 25
- boiling point
- 221.5
- density
- 0.904
Sources (9)
via Wikidata · CC0
~29 min read
Encyclopedic overview
45 sectionsContents
- Medical uses
- Epilepsy
- Psychiatric disorders
- Other uses
- Contraindications
- Adverse effects
- Pregnancy
- Elderly
- Overdose and toxicity
- Interactions
- Pharmacology
- Pharmacodynamics
- Endocrine actions
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Restrictions
- Approval status
- Off-label uses
- Formulations
- Terminology
- Brand names of valproic acid
- Brand names of sodium valproate
- Portugal
- United States
- Australia
- New Zealand
- UK
- UK only
- Germany, Switzerland, Norway, Finland, Sweden
- South Africa
- Malaysia
- Romania
- Canada
- Japan
- Europe
- Taiwan
- Iran
- Israel
- India, Russia and [[Commonwealth of Independent States|CIS]] countries
- Uruguay
- Brand names of valproate semisodium
- Research
- References
Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and as a mood stabilizer in the treatment of bipolar disorder. They are useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. They can be given intravenously or by mouth, and the tablet forms exist in both long- and short-acting formulations.
Common side effects of valproate include nausea, vomiting, somnolence, and dry mouth. Serious side effects can include liver failure, and regular monitoring of liver function tests is therefore recommended. Other serious risks include pancreatitis and an increased suicide risk.
Excerpted from Wikipedia’s “valproic acid” article, available under the CC BY-SA 4.0 licence.