Divalproex sodium (CHEM002214)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:04 UTC
Update Date2026-05-21 16:37:04 UTC
Accession NumberCHEM002214
Identification
Common NameDivalproex sodium
ClassSmall Molecule
DescriptionA fatty acid with anticonvulsant properties used in the treatment of epilepsy. The mechanisms of its therapeutic actions are not well understood. It may act by increasing gamma-aminobutyric acid levels in the brain or by altering the properties of voltage dependent sodium channels. [PubChem]
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Anticonvulsant
  • Antimanic Agent
  • Drug
  • Enzyme Inhibitor
  • GABA Agent
  • Human Neurotoxin
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Divalproex sodiumChEBI
Semisodium valproateChEBI
Sodium divalproateChEBI
Sodium hydrogen bis(2-propylpentanoate)ChEBI
Sodium hydrogen bis(2-propylvalerate)ChEBI
Sodium hydrogen divalproateChEBI
Valproate semisodiqueChEBI
Valproato semisodicoChEBI
Valproatum seminatricumChEBI
DepakoteKegg
Semisodium valproic acidGenerator
Sodium divalproic acidGenerator
Sodium hydrogen bis(2-propylpentanoic acid)Generator
Sodium hydrogen bis(2-propylvaleric acid)Generator
Sodium hydrogen divalproic acidGenerator
Valproic acid semisodiqueGenerator
Valproic acid semisodiumGenerator
Chemical FormulaC16H31NaO4
Average Molecular Mass310.405 g/mol
Monoisotopic Mass310.212 g/mol
CAS Registry Number76584-70-8
IUPAC NameNot Available
Traditional Namesodium valproic acid valproate
SMILES[Na+].CCCC(CCC)C(O)=O.CCCC(CCC)C([O-])=O
InChI IdentifierInChI=1S/2C8H16O2.Na/c2*1-3-5-7(6-4-2)8(9)10;/h2*7H,3-6H2,1-2H3,(H,9,10);/q;;+1/p-1
InChI KeyMSRILKIQRXUYCT-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acids and conjugates. These are aliphatic monocarboxylic acids with a saturated or unsaturated aliphatic tail (with at least 4 Carbon atoms).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentFatty acids and conjugates
Alternative Parents
Substituents
  • Fatty acid
  • Organic alkali metal salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point222°C
Boiling PointNot Available
SolubilitySlightly soluble (2000 mg/L)
Predicted Properties
PropertyValueSource
logP2.8ChemAxon
pKa (Strongest Acidic)5.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity40.25 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityDivalproex binds to and inhibits GABA transaminase. The drug's anticonvulsant activity may be related to increased brain concentrations of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter in the CNS, by inhibiting enzymes that catabolize GABA or block the reuptake of GABA into glia and nerve endings. Divalproex may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels.
MetabolismDivalproex is metabolized almost entirely by the liver. Mitochondrial ß-oxidation is the other major metabolic pathway, typically accounting for over 40% of the dose.
Toxicity ValuesNot Available
Lethal DoseFatalities have been reported; however patients have recovered from divalproex levels as high as 2120 ug/mL. (1)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsOverdosage with divalproex may result in somnolence,heart block,and deep coma. Fatalities have been reported; however patients have recovered from divalproex levels as high as 2120 µg/mL.
TreatmentIn overdose situations, the fraction of drug not bound to protein is high and hemodialysis or tandem hemodialysis plus hemoperfusion may result in significant removal of drug. The benefit of gastric lavage or emesis will vary with the time since ingestion. General supportive measures should be applied with particular attention to the maintenance of adequate urinary output. (8)
Concentrations
Not Available
DrugBank IDDBSALT000185
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkValproate
Chemspider IDNot Available
ChEBI ID4667
PubChem Compound ID53519
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Daniel Aubert, Francis Blanc, Henri Desmolin, Michel Morre, Lucette Sindely, “Valproic acid preparations.” U.S. Patent US5017613, issued January, 1965.

MSDSNot Available
General ReferencesNot Available