valproic acid (CHEBI:39867)

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CHEBI:39867 - valproic acid

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ChEBI Name	valproic acid

ChEBI ID	CHEBI:39867

Definition	A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:9926, CHEBI:39858, CHEBI:115217

Supplier Information	ChemicalBook:CB7149528, eMolecules:593399, ZINC000003008621

Download	Molfile XML SDF

more structures >>

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Mrv0541 12311313023D

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Mrv0541 12311313023D

26 25 0 0 0 0 999 V2000

-0.8928 1.8943 1.6256 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.7746 2.0013 2.8860 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0512 -1.0929 -0.8888 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.8800 0.4777 0.9922 C 0 0 2 0 0 0 0 0 0 0 0 0

0.7849 -1.2849 -2.1819 C 0 0 1 0 0 0 0 0 0 0 0 0

0.7130 -2.7127 -2.7597 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0574 0.3239 -0.2452 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0667 0.0021 0.9089 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4372 0.6579 0.0839 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0094 1.5982 -0.4490 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2409 2.6183 0.8839 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1203 2.1843 1.9149 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7231 3.0138 3.2896 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4266 1.3075 3.6538 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8147 1.7737 2.6476 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0986 -1.2935 -1.1345 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2471 -1.8471 -0.1538 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9049 0.2344 0.6954 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5939 -0.2534 1.7548 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4444 -0.5752 -2.9408 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8377 -1.0700 -1.9826 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3359 -2.7830 -3.6529 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3132 -2.9667 -3.0297 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0774 -3.4376 -2.0291 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3162 1.0285 -0.9981 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8994 0.2015 1.1093 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 4 1 0 0 0 0

5 3 1 0 0 0 0

3 7 1 0 0 0 0

7 4 1 0 0 0 0

5 6 1 0 0 0 0

7 9 1 0 0 0 0

9 8 1 0 0 0 0

9 10 2 0 0 0 0

1 11 1 0 0 0 0

1 12 1 0 0 0 0

2 13 1 0 0 0 0

2 14 1 0 0 0 0

2 15 1 0 0 0 0

3 16 1 0 0 0 0

3 17 1 0 0 0 0

4 18 1 0 0 0 0

4 19 1 0 0 0 0

5 20 1 0 0 0 0

5 21 1 0 0 0 0

6 22 1 0 0 0 0

6 23 1 0 0 0 0

6 24 1 0 0 0 0

7 25 1 0 0 0 0

8 26 1 0 0 0 0

M END): 17 ms

reading 26 atoms

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26 atoms created

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Wikipedia	License
Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and bipolar disorder and prevent migraine headaches. They are useful for the prevention of seizures in those with absence seizures, partial seizures, and generalized seizures. They can be given intravenously or by mouth, and the tablet forms exist in both long- and short-acting formulations. Common side effects of valproate include nausea, vomiting, somnolence, and dry mouth. Serious side effects can include liver failure, and regular monitoring of liver function tests is therefore recommended. Other serious risks include pancreatitis and an increased suicide risk. Valproate is known to cause serious abnormalities or birth defects in the unborn child if taken during pregnancy, and is contra-indicated for women of childbearing age unless the drug is essential to their medical condition and the person is also prescribed a contraceptive. Reproductive warnings have also been issued for men using the drug. The United States Food and Drug Administration has indicated a black box warning given the frequency and severity of the side effects and teratogenicity. Additionally, there is also a black box warning due to risk of hepatotoxicity and pancreatitis. As of 2022 the drug was still prescribed in the UK to potentially pregnant women, but use declined by 51% from 2018–19 to 2020–21. Vaproate has been in use in Japan for the prophylaxis of migraine since 2011. It is approved as an antimaniac and anti seizure in Japan as well. In UK, vaproate is approved for bipolar mania and epilepsy, and both valproate and divalproex are approved, although divalproex sodium is known as valproate semisodium. Valproate's precise mechanism of action is unclear. Proposed mechanisms include affecting GABA levels, blocking voltage-gated sodium channels, inhibiting histone deacetylases, and increasing LEF1. Valproic acid is a branched short-chain fatty acid (SCFA), a derivative of valeric acid. Valproate was originally synthesized in 1881 and came into medical use in 1962. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 174th most commonly prescribed medication in the United States, with more than 2 million prescriptions.
Read full article at Wikipedia

Formula

C8H16O2

Net Charge

Average Mass

144.21140

Monoisotopic Mass

144.11503

InChI

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

CCCC(CCC)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	GABA agent A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems. EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). teratogenic agent A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.

Application(s):	GABA agent A substance, such as agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function, used for its pharmacological actions on GABAergic systems. anticonvulsant A drug used to prevent seizures or reduce their severity. psychotropic drug A loosely defined grouping of drugs that have effects on psychological function. neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. antimanic drug Antimanic drugs are agents used to treat bipolar disorders or mania associated with other affective disorders.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	valproic acid (CHEBI:39867) has functional parent valeric acid (CHEBI:17418) valproic acid (CHEBI:39867) has role anticonvulsant (CHEBI:35623) valproic acid (CHEBI:39867) has role antimanic drug (CHEBI:35477) valproic acid (CHEBI:39867) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115) valproic acid (CHEBI:39867) has role GABA agent (CHEBI:51374) valproic acid (CHEBI:39867) has role neuroprotective agent (CHEBI:63726) valproic acid (CHEBI:39867) has role psychotropic drug (CHEBI:35471) valproic acid (CHEBI:39867) has role teratogenic agent (CHEBI:50905) valproic acid (CHEBI:39867) is a branched-chain fatty acid (CHEBI:35819) valproic acid (CHEBI:39867) is a branched-chain saturated fatty acid (CHEBI:39417) valproic acid (CHEBI:39867) is conjugate acid of valproate (CHEBI:60654)

Incoming	valpromide (CHEBI:74562) has functional parent valproic acid (CHEBI:39867) valproate semisodium (CHEBI:4667) has part valproic acid (CHEBI:39867) valproate (CHEBI:60654) is conjugate base of valproic acid (CHEBI:39867)

IUPAC Name

2-propylpentanoic acid

INNs	Sources
acide valproïque	ChemIDplus
ácido valproico	ChemIDplus
acidum valproicum	ChemIDplus
valproic acid	ChemIDplus

Synonyms	Sources
2-n-propyl-n-valeric acid	NIST Chemistry WebBook
2-PROPYL-PENTANOIC ACID	PDBeChem
2-propylpentanoic acid	ChEMBL
2-propylvaleric acid	ChemIDplus
4-heptanecarboxylic acid	ChemIDplus
di-n-propylacetic acid	ChemIDplus
Di-n-propylessigsäure	ChemIDplus
dipropylacetic acid	NIST Chemistry WebBook
DPA	NIST Chemistry WebBook
n-DPA	DrugBank
VALPROIC ACID	ChEMBL
Valproinsäure	ChEBI
VPA	ChEBI

Brand Name	Source
Depakene	KEGG DRUG

Manual Xrefs	Databases
2803	DrugCentral
2PP	PDBeChem
C07185	KEGG COMPOUND
D00399	KEGG DRUG
DB00313	DrugBank
HMDB0001877	HMDB
LMFA01020291	LIPID MAPS
LSM-4620	LINCS
Valproic_Acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
1750447	Beilstein Registry Number	ChemIDplus
1750447	Reaxys Registry Number	Reaxys
99-66-1	CAS Registry Number	ChemIDplus
99-66-1	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
11716839	PubMed citation	Europe PMC
12475192	PubMed citation	Europe PMC
15124690	PubMed citation	Europe PMC
15560954	PubMed citation	Europe PMC
15578701	PubMed citation	Europe PMC
16496131	PubMed citation	Europe PMC
16621443	PubMed citation	Europe PMC
16759735	PubMed citation	Europe PMC
17156483	PubMed citation	Europe PMC
17273758	PubMed citation	Europe PMC
19280426	PubMed citation	Europe PMC
19318486	PubMed citation	Europe PMC
23792104	PubMed citation	Europe PMC
23810771	PubMed citation	Europe PMC
23949302	PubMed citation	Europe PMC
24135375	PubMed citation	Europe PMC
24200999	PubMed citation	Europe PMC
24348849	PubMed citation	Europe PMC
8558327	PubMed citation	Europe PMC
8681902	PubMed citation	Europe PMC

Last Modified

22 February 2017

General Comment
2011-02-11	An anti-epilectic and anti-carcinogenic drug with toxic and teratogenic properties, which dissolves to valproate in the gut.

CHEBI:39867 - valproic acid

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