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Substance Name: Valproic acid [USAN:USP:INN:BAN]
RN: 99-66-1
UNII: 614OI1Z5WI
InChIKey: NIJJYAXOARWZEE-UHFFFAOYSA-N

Note

  • A 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.

Molecular Formula

  • C8-H16-O2

Molecular Weight

  • 144.2124
 

Classification Codes

  • Anticonvulsant
  • Anticonvulsants
  • Antimanic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • GABA Agents
  • Human Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Tranquilizing Agents

Names and Synonyms

Name of Substance

  • Valproic acid
  • Valproic acid [USAN:USP:INN:BAN]

MeSH Heading

  • Valproic acid

Synonyms

  • 2-Propylpentanoic acid
  • 2-Propylvaleric acid
  • 3-02-00-00807 (Beilstein Handbook Reference)
  • 4-Heptanecarboxylic acid
  • 44089
  • Abbott 44090
  • Acetic acid, dipropyl-
  • Acide valproique
  • Acide valproique [INN-French]
  • Acido valproico
  • Acido valproico [INN-Spanish]
  • Acidum valproicum
  • Acidum valproicum [INN-Latin]
  • AI3-10500
  • BRN 1750447
  • Depakene
  • Depakin
  • Depakine
  • Di-n-propylacetic acid
  • Di-n-propylessigsaure
  • Di-n-propylessigsaure [German]
  • Dipropylacetate
  • Dipropylacetic acid
  • DPA (VAN)
  • EC 202-777-3
  • EINECS 202-777-3
  • Ergenyl
  • HSDB 3582
  • Kyselina 2-propylvalerova
  • Kyselina 2-propylvalerova [Czech]
  • Mylproin
  • Myproic acid
  • n-Dipropylacetic acid
  • NSC 93819
  • Propylvaleric acid
  • Stavzor
  • UNII-614OI1Z5WI
  • Valproate
  • Valproic acid
  • Vupral

Systematic Names

  • 2-Propylvaleric acid
  • Pentanoic acid, 2-propyl-
  • Valeric acid, 2-propyl-

Superlist Names

  • Valproate
  • Valproic acid

Registry Numbers

CAS Registry Number

  • 99-66-1

FDA UNII

  • 614OI1Z5WI

Related Registry Number

  • 76584-70-8 (hydrochloride salt (2:1))

System Generated Number

  • 0000099661

Structure Descriptors

InChI

1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

InChIKey

NIJJYAXOARWZEE-UHFFFAOYSA-N

Smiles

C(CCC)(CCC)C(O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 375mg/kg (375mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Critical Care Medicine. Vol. 21, Pg. 299, 1993.
child TDLo oral 412mg/kg (412mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: COMA
Journal of Analytical Toxicology. Vol. 20, Pg. 55, 1996.
child TDLo oral 10500mg/kg/30 (10500mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Diseases of Children. Vol. 138, Pg. 912, 1984.
child TDLo unreported 1800mg/kg/60D (1800mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS
Lancet. Vol. 1, Pg. 1196, 1980.
guinea pig LD50 oral 824mg/kg (824mg/kg)   "Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 39, 1968.
human TDLo oral 13333ug/kg/D- (13.333mg/kg) BEHAVIORAL: SLEEP New England Journal of Medicine. Vol. 301, Pg. 435, 1979.
man LDLo oral 736mg/kg (736mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
Journal of Analytical Toxicology. Vol. 22, Pg. 537, 1998.
man TDLo oral 21mg/kg/2D-I (21mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Neurology. Vol. 37, Pg. 886, 1987.
man TDLo oral 429mg/kg (429mg/kg) BEHAVIORAL: COMA Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 219, 2000.
mouse LD50 intraperitoneal 470mg/kg (470mg/kg)   Chimica Therapeutica. Vol. 3, Pg. 430, 1968.
mouse LD50 oral 1098mg/kg (1098mg/kg)   European Patent Application. Vol. #78785,
mouse LD50 subcutaneous 860mg/kg (860mg/kg)   "Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 38, 1968.
rabbit LD50 intraperitoneal 1200mg/kg (1200mg/kg)   "Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 39, 1968.
rat LD50 oral 670mg/kg (670mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
women TDLo oral 100mg/kg/10D- (100mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BRAIN AND COVERINGS: ENCEPHALITIS

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG
Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 219, 2000.
women TDLo oral 330mg/kg (330mg/kg) BEHAVIORAL: COMA

BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 18, Pg. 508, 2000.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Boiling Point 222 deg C   EXP
pKa Dissociation Constant 4.6 (none)   EXP
log P (octanol-water) 2.75 (none)   EXP
Water Solubility 2000 mg/L 20 EXP
Vapor Pressure 0.046 mm Hg 25 EST
Henry's Law Constant 3.00E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.18E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.