ChemFOnt: Showing chemical card for Valproic acid (CFc000001249)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:50 UTC

Chemfont ID

CFc000001249

Molecule Identification

Common Name

Valproic acid

Definition

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-N-Propyl-N-valeric acid	ChEBI
2-PROPYL-pentanoIC ACID	ChEBI
2-Propylpentanoic acid	ChEBI
2-Propylvaleric acid	ChEBI
4-Heptanecarboxylic acid	ChEBI
Acide valproique	ChEBI
Acido valproico	ChEBI
Acidum valproicum	ChEBI
Depakene	ChEBI
Di-N-propylacetic acid	ChEBI
Di-N-propylessigsaeure	ChEBI
Dipropylacetic acid	ChEBI
DPA	ChEBI
N-DPA	ChEBI
Valproinsaeure	ChEBI
VPA	ChEBI
2-N-Propyl-N-valerate	Generator
2-PROPYL-pentanoate	Generator
2-Propylpentanoate	Generator
2-Propylvalerate	Generator
4-Heptanecarboxylate	Generator
Di-N-propylacetate	Generator
Dipropylacetate	Generator
Valproate	Generator
(N-C3H7)2chcooh	HMDB
(S)-2-Propyl-4-pentanoate	HMDB
(S)-2-Propyl-4-pentanoic acid	HMDB
Alti-valproic	HMDB
Apo-divalproex	HMDB
Apo-valproic	HMDB
Apo-valproic syrup	HMDB
Avugane	HMDB
Baceca	HMDB
Convulex	HMDB
Delepsine	HMDB
Depakin	HMDB
Depakin chrono	HMDB
Depakine	HMDB
Depakine chrono	HMDB
Deproic	HMDB
Di-N-propylessigsaure	HMDB
Divalproex	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
Epiject i.v.	HMDB
Epilex	HMDB
Epilim	HMDB
Epival	HMDB
Epival er	HMDB
Ergenyl	HMDB
Gen-divalproex	HMDB
Kyselina 2-propylvalerova	HMDB
Med valproic	HMDB
Mylproin	HMDB
Myproate	HMDB
Myproic acid	HMDB
N-Dipropylacetic acid	HMDB
Novo-divalproex	HMDB
Novo-valproic	HMDB
Novo-valproic - ecc	HMDB
Novo-valproic soft gel cap	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-Valproate	HMDB
PMS-Valproic acid	HMDB
PMS-Valproic acid e.c.	HMDB
Propylvaleric acid	HMDB
Ratio-valproic - ecc	HMDB
S(-)-4-En-valproate	HMDB
S(-)-4-En-valproic acid	HMDB
S-2-N-Propyl-4-pentenoate	HMDB
S-2-N-Propyl-4-pentenoic acid	HMDB
Sandoz valproic	HMDB
Savicol	HMDB
Sprinkle	HMDB
Valcote	HMDB
Valparin	HMDB
Valproic acid usp	HMDB
Dipropyl acetate	HMDB
Valproate, sodium	HMDB
Calcium, valproate	HMDB
Convulsofin	HMDB
Semisodium valproate	HMDB
Sodium valproate	HMDB
Valproate calcium	HMDB
Valproate, calcium	HMDB
Valproic acid, sodium salt (2:1)	HMDB
Acetate, dipropyl	HMDB
Depakote	HMDB
Divalproex sodium	HMDB
Magnesium valproate	HMDB
Sodium, divalproex	HMDB
Sodium, valproate	HMDB
Vupral	HMDB
2 Propylpentanoic acid	HMDB
Acid, propylisopropylacetic	HMDB
Acid, valproic	HMDB
Calcium valproate	HMDB
Propylisopropylacetic acid	HMDB
Valproate sodium	HMDB
Valproate, magnesium	HMDB
Valproate, semisodium	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

2-propylpentanoic acid

Traditional Name

valproic acid

CAS Registry Number

99-66-1

SMILES

CCCC(CCC)C(O)=O

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

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain fatty acid (CHEBI:39867 )
branched-chain saturated fatty acid (CHEBI:39867 )
Branched fatty acids (LMFA01020291 )

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Leukocytic disorder

Leukemia (HMDB: HMDB0001877)
Leukemia (HMDB: HMDB0001877)

Hyperammonemia (HMDB: HMDB0001877)

Vascular disorder

Hypotension (HMDB: HMDB0001877)

Nervous system disorder

Central nervous system disorder

Spina bifida (HMDB: HMDB0001877)

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0001877)

Coma (HMDB: HMDB0001877)

Observation

Renal system and urinary system

Renal disorder

Renal failure (HMDB: HMDB0001877)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15954179)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0001877)

Organ

Brain (HMDB: HMDB0001877)
Liver (HMDB: HMDB0001877)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001877)

Route of exposure

Parenteral

Inhalation (HMDB: HMDB0001877)

Enteral

Ingestion (HMDB: HMDB0001877)
Gastrointestinal (HMDB: HMDB0001877)

Source

Exogenous

Exogenous (HMDB: HMDB0001877)

Food

Food (HMDB: HMDB0001877)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001877)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001877)
Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Lipid metabolism pathway (HMDB: HMDB0001877)

Cellular process

Cell signaling (HMDB: HMDB0001877)

Biochemical process

Lipid transport (HMDB: HMDB0001877)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.36 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.25 m³·mol⁻¹	ChemAxon
Polarizability	17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon