FComEx: Valproic acid (PC000533)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:14 UTC

Update date

2017-01-19 02:36:27 UTC

FoodComEx ID

PC000533

FoodDB Record

FDB022722

Chemical Information

Name

Valproic acid

Description

Valproic 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 Number

99-66-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(n-C3H7)2CHCOOH	hmdb
(S)-2-propyl-4-pentanoate	hmdb
(S)-2-propyl-4-pentanoic acid	hmdb
2 PP (base)	hmdb
2-N-Propyl-N-valerate	Generator
2-n-Propyl-n-valeric acid	hmdb
2-propyl-Pentanoate	hmdb
2-propyl-Pentanoic acid	hmdb
2-Propylpentanoate	hmdb
2-Propylpentanoic acid	hmdb
2-propylpentanoic acid (ACD/Name 4.0)	hmdb
2-Propylvalerate	Generator
2-Propylvaleric acid	hmdb
4-Heptanecarboxylate	Generator
4-Heptanecarboxylic acid	hmdb
Acide valproique	ChEBI
acide valproique [inn-french]	hmdb
Acido valproico	ChEBI
acido valproico [inn-spanish]	hmdb
Acidum valproicum	ChEBI
acidum valproicum [inn-latin]	hmdb
Alti-valproic	hmdb
APO-divalproex	hmdb
Apo-valproic	hmdb
Apo-valproic syrup	hmdb
Avugane	hmdb
Baceca	hmdb
Convulex	hmdb
Delepsine	hmdb
Depakene	hmdb
Depakene Cap 250mg	hmdb
Depakene Cap 500mg	hmdb
Depakin	hmdb
Depakin chrono	hmdb
Depakine	hmdb
Depakine chrono	hmdb
Deproic	hmdb
Di-N-propylacetate	Generator
Di-n-propylacetic acid	hmdb
Di-N-propylessigsaeure	ChEBI
Di-n-propylessigsaure	hmdb
Di-n-propylessigsaure [german]	hmdb
Dipropylacetate	hmdb
Dipropylacetic acid	hmdb
Divalproex	hmdb
Divalproex-125	hmdb
Divalproex-250	hmdb
Divalproex-500	hmdb
DOM-divalproex	hmdb
Dom-valproate	hmdb
DOM-valproic	hmdb
Dom-valproic acid	hmdb
DOM-valproic acid E.C.	hmdb
Dom-valproic acid syrup	hmdb
DPA (van)	hmdb
Epiject I.V.	hmdb
Epilex	hmdb
Epilim	hmdb
Epival	hmdb
Epival Ect 125mg	hmdb
Epival Ect 250mg	hmdb
Epival Ect 500mg	hmdb
Epival er	hmdb
Ergenyl	hmdb
Gen-divalproex	hmdb
Gen-Valproic - Cap 250mg	hmdb
Kyselina 2-propylvalerova	hmdb
Kyselina 2-propylvalerova [Czech]	hmdb
Med valproic	hmdb
Mylproin	hmdb
N-dipropylacetic acid	hmdb
N-DPA	hmdb
nchembio815-comp21	hmdb
Novo-divalproex	hmdb
Novo-valproic	hmdb
Novo-Valproic - ECC	hmdb
Novo-valproic soft gel cap	hmdb
Nu-Divalproex 125mg	hmdb
Nu-Divalproex 250mg	hmdb
Nu-Divalproex 500mg	hmdb
Nu-valproic	hmdb
PEAC	hmdb
Penta-valproic	hmdb
PHL-valproate	hmdb
PHL-valproic acid	hmdb
PHL-valproic acid E.C.	hmdb
PMS-Divalproex	hmdb
PMS-Divalproex (125mg)	hmdb
PMS-Divalproex (500mg)	hmdb
PMS-valproate	hmdb
PMS-valproic acid	hmdb
PMS-valproic acid E.C.	hmdb
Propylvaleric acid	hmdb
Ratio-Valproic - ECC	hmdb
Ratio-Valproic 50mg/mL Syrup	hmdb
Ratio-Valproic-Cap 250mg	hmdb
S-2-n-Propyl-4-pentenoate	hmdb
S-2-n-Propyl-4-pentenoic acid	hmdb
S(-)-4-En-valproate	hmdb
S(-)-4-En-valproic acid	hmdb
Sandoz valproic	hmdb
Savicol	hmdb
Sodium hydrogen divalproate	hmdb
Sodium hydrogen divalproic acid	hmdb
Sprinkle	hmdb
Valcote	hmdb
Valparin	hmdb
Valproate semisodique [french]	hmdb
Valproate semisodium	hmdb
Valproato semisodico [spanish]	hmdb
Valproatum seminatricum [latin]	hmdb
Valproic acid [usan:ban:inn]	hmdb
Valproic acid USP	hmdb
Valproic acid USP24	hmdb
Valproic-250	hmdb
Valproinsaeure	ChEBI
VPA	hmdb

Chemical Formula

C8H16O2

IUPAC name

2-propylpentanoic acid

InChI Identifier

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

Isomeric SMILES

CCCC(CCC)C(O)=O

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents