Record Information
Version1.0
Creation date2015-10-09 22:31:14 UTC
Update date2017-01-19 02:36:27 UTC
FoodComEx IDPC000533
FoodDB RecordFDB022722
Chemical Information
NameValproic acid
DescriptionValproic acid (VPA) is considered to be a drug of first choice and one of the most frequently-prescribed antiepileptic drugs worldwide for the therapy of generalized and focal epilepsies, including special epileptic. It is a broad-spectrum antiepileptic drug and is usually well tolerated. Rarely, serious complications may occur in some patients, including hemorrhagic pancreatitis, coagulopathies, bone marrow suppression, VPA-induced hepatotoxicity and encephalopathy, but there is still a lack of knowledge about the incidence and occurrence of these special side effects. VPA has been approved for stabilization of manic episodes in patients with bipolar disorder. It is also used to treat migraine headaches and schizophrenia. As the use of VPA increases, the number of both accidental and intentional exposures increases. This is paralleled by more reports of VPA-induced toxicity. VPA is relatively contraindicated in pregnancy due to its teratogenicity. It is a known folate antagonist, which can cause neural tube defects. Thus, folic acid supplements may alleviate teratogenic problems. Women who become pregnant whilst taking valproate should be counselled as to its risks. VPA is an inhibitor of the enzyme histone deacetylase 1 (HDAC1). HDAC1 is needed for HIV to remain in infected cells. Patients treated with valproic acid in addition to highly active antiretroviral therapy (HAART) showed a median 75% reduction in latent HIV infection. VPA is believed to affect the function of the neurotransmitter GABA (as a GABA transaminase inhibitor) in the human brain. Valproic Acid dissociates to the valproate ion in the gastrointestinal tract. (PMID: 18201150, 17496767) [HMDB]
CAS Number99-66-1
Structure
Thumb
Synonyms
SynonymSource
(n-C3H7)2CHCOOHhmdb
(S)-2-propyl-4-pentanoatehmdb
(S)-2-propyl-4-pentanoic acidhmdb
2 PP (base)hmdb
2-N-Propyl-N-valerateGenerator
2-n-Propyl-n-valeric acidhmdb
2-propyl-Pentanoatehmdb
2-propyl-Pentanoic acidhmdb
2-Propylpentanoatehmdb
2-Propylpentanoic acidhmdb
2-propylpentanoic acid (ACD/Name 4.0)hmdb
2-PropylvalerateGenerator
2-Propylvaleric acidhmdb
4-HeptanecarboxylateGenerator
4-Heptanecarboxylic acidhmdb
Acide valproiqueChEBI
acide valproique [inn-french]hmdb
Acido valproicoChEBI
acido valproico [inn-spanish]hmdb
Acidum valproicumChEBI
acidum valproicum [inn-latin]hmdb
Alti-valproichmdb
APO-divalproexhmdb
Apo-valproichmdb
Apo-valproic syruphmdb
Avuganehmdb
Bacecahmdb
Convulexhmdb
Delepsinehmdb
Depakenehmdb
Depakene Cap 250mghmdb
Depakene Cap 500mghmdb
Depakinhmdb
Depakin chronohmdb
Depakinehmdb
Depakine chronohmdb
Deproichmdb
Di-N-propylacetateGenerator
Di-n-propylacetic acidhmdb
Di-N-propylessigsaeureChEBI
Di-n-propylessigsaurehmdb
Di-n-propylessigsaure [german]hmdb
Dipropylacetatehmdb
Dipropylacetic acidhmdb
Divalproexhmdb
Divalproex-125hmdb
Divalproex-250hmdb
Divalproex-500hmdb
DOM-divalproexhmdb
Dom-valproatehmdb
DOM-valproichmdb
Dom-valproic acidhmdb
DOM-valproic acid E.C.hmdb
Dom-valproic acid syruphmdb
DPA (van)hmdb
Epiject I.V.hmdb
Epilexhmdb
Epilimhmdb
Epivalhmdb
Epival Ect 125mghmdb
Epival Ect 250mghmdb
Epival Ect 500mghmdb
Epival erhmdb
Ergenylhmdb
Gen-divalproexhmdb
Gen-Valproic - Cap 250mghmdb
Kyselina 2-propylvalerovahmdb
Kyselina 2-propylvalerova [Czech]hmdb
Med valproichmdb
Mylproinhmdb
N-dipropylacetic acidhmdb
N-DPAhmdb
nchembio815-comp21hmdb
Novo-divalproexhmdb
Novo-valproichmdb
Novo-Valproic - ECChmdb
Novo-valproic soft gel caphmdb
Nu-Divalproex 125mghmdb
Nu-Divalproex 250mghmdb
Nu-Divalproex 500mghmdb
Nu-valproichmdb
PEAChmdb
Penta-valproichmdb
PHL-valproatehmdb
PHL-valproic acidhmdb
PHL-valproic acid E.C.hmdb
PMS-Divalproexhmdb
PMS-Divalproex (125mg)hmdb
PMS-Divalproex (500mg)hmdb
PMS-valproatehmdb
PMS-valproic acidhmdb
PMS-valproic acid E.C.hmdb
Propylvaleric acidhmdb
Ratio-Valproic - ECChmdb
Ratio-Valproic 50mg/mL Syruphmdb
Ratio-Valproic-Cap 250mghmdb
S-2-n-Propyl-4-pentenoatehmdb
S-2-n-Propyl-4-pentenoic acidhmdb
S(-)-4-En-valproatehmdb
S(-)-4-En-valproic acidhmdb
Sandoz valproichmdb
Savicolhmdb
Sodium hydrogen divalproatehmdb
Sodium hydrogen divalproic acidhmdb
Sprinklehmdb
Valcotehmdb
Valparinhmdb
Valproate semisodique [french]hmdb
Valproate semisodiumhmdb
Valproato semisodico [spanish]hmdb
Valproatum seminatricum [latin]hmdb
Valproic acid [usan:ban:inn]hmdb
Valproic acid USPhmdb
Valproic acid USP24hmdb
Valproic-250hmdb
ValproinsaeureChEBI
VPAhmdb
Chemical FormulaC8H16O2
IUPAC name2-propylpentanoic acid
InChI IdentifierInChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChI KeyNIJJYAXOARWZEE-UHFFFAOYSA-N
Isomeric SMILESCCCC(CCC)C(O)=O
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci B396
AKSci J91459
Toronto Research Chemicals V094750