valproic acid   Click here for help

GtoPdb Ligand ID: 7009

Synonyms: A-44090 | Depakote® | Epilim® | valproate sodium
Approved drug PDB Ligand
valproic acid is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Valproic acid is a fatty acid with anticonvulsant properties. It is commonly administered in a salt preparation, valproate sodium.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: valproic acid

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 37.3
Molecular weight 144.12
XLogP 2.74
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCC(C(=O)O)CCC
Isomeric SMILES CCCC(C(=O)O)CCC
InChI InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChI Key NIJJYAXOARWZEE-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Valproic acid is currently approved for the treatment of various seizure disorders, manic episodes of bipolar disorder and migraine headache. Valproic acid is, in addition, a histone deacetylase (HDAC) inhibitor and is being investigated as a treatment for HIV infection and various cancers.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Inhibition of succinic semi-aldehyde dehydrogenase (ALDH5A1) may contribute to the elevated levels of cerebral and cerebellar GABA observed as a result of valproic acid administration (in animal models). ALDH5A1 is a GABA degradative enzyme. Increased levels of GABA cause neuro-inhibition and may be mechanistically linked to the drug's anticonvulsant and mood-stabilising effects. However, we have been unable to find affinity data for this drug to substantiate this proposed MMOA.

Valproic acid is also an inhibitor of Class I and II HDACs. In relation to HIV infection and the potential antiviral effects of valproic acid, HDAC1 is required for persistence of HIV in infected cells.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com