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Details

Stereochemistry ACHIRAL
Molecular Formula C8H17NO
Molecular Weight 143.2267
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALPROMIDE

SMILES

CCCC(CCC)C(N)=O

InChI

InChIKey=OMOMUFTZPTXCHP-UHFFFAOYSA-N
InChI=1S/C8H17NO/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H2,9,10)

HIDE SMILES / InChI

Molecular Formula C8H17NO
Molecular Weight 143.2267
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Valpromide (2-propylpentanamide) is a derivative of valproic acid. Bio-pharmacological data show several possible mechanisms of action involving an increase in GABA levels in brain as well as changes in membrane conductance on neurons. Valpromide has been shown to decrease aggressivity in stress-induced animals, to regulate anxious induced behaviours, as well as to potentiate central sedative compounds. It produces a significant increase of cognitive functions. Psychopathological experiments have shown: a wakening of personality, euphoric effects, an improvement of social behaviour, a stabilization of mood in affective disorders. Valpromide is indicated for the treatment of bipolar disorder (manic episodes). It is marketed in some Europe countries.

Originator

Sources: Fischer, E., Dilthey, A., 1902. Einwirkung von Ammoniak auf die Alkylmalonester. Chemische Berichte 35, 844–856.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/10670421 | http://www.drugfuture.com/chemdata/valpromide.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEPAMIDE

Approved Use

Traitement des épisodes maniaques du trouble bipolaire en cas de contre-indication ou d'intolérance au lithium. La poursuite du traitement après l’épisode maniaque peut être envisagée chez les patients ayant répondu au valpromide lors de l’épisode aigu.
PubMed

PubMed

TitleDatePubMed
[Cerebral edema with hyperammonemia in valpromide poisoning. Manifestation in an adult, of a partial deficit in type I carbamylphosphate synthetase].
1988 Nov 5
New CNS-active drugs which are second-generation valproic acid: can they lead to the development of a magic bullet?
2003 Apr
Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy.
2003 Aug
[The Charles Bonnet syndrome: a case report and a brief review].
2003 Jan-Feb
Inhibition of histone deacetylase activity by valproic acid blocks adipogenesis.
2004 Apr 30
Amidic modification of valproic acid reduces skeletal teratogenicity in mice.
2004 Feb
[Deep lactic acidosis after valproate self-poisoning].
2004 Oct
Identification of early-responsive genes correlated to valproic acid-induced neural tube defects in mice.
2005 Apr
Catalytic mechanism of limonene epoxide hydrolase, a theoretical study.
2005 Oct 19
S-2-pentyl-4-pentynoic hydroxamic acid and its metabolite s-2-pentyl-4-pentynoic acid in the NMRI-exencephaly-mouse model: pharmacokinetic profiles, teratogenic effects, and histone deacetylase inhibition abilities of further valproic acid hydroxamates and amides.
2006 Apr
The effects of central nervous system-active valproic acid constitutional isomers, cyclopropyl analogs, and amide derivatives on neuronal growth cone behavior.
2007 Mar
Acute and long-term treatment of mania.
2008
The effectiveness of anticonvulsants in psychiatric disorders.
2008
Lipid peroxidation in women with epilepsy.
2008 Jan
Valproic acid extends Caenorhabditis elegans lifespan.
2008 Jun
Valproic acid induces functional heat-shock protein 70 via Class I histone deacetylase inhibition in cortical neurons: a potential role of Sp1 acetylation.
2009 Nov
Metabolic activation capacity by primary hepatocytes expands the applicability of the embryonic stem cell test as alternative to experimental animal testing.
2010 Aug
[Pharmacokinetics of biological tags in a case of acute valpromide self poisoning].
2010 Mar-Apr
Inhibition of class II histone deacetylases in the spinal cord attenuates inflammatory hyperalgesia.
2010 Sep 7
Patents

Sample Use Guides

Recommended initial dose 750 mg per day
Route of Administration: Oral
1 mM valpromide affects epileptiform activities of neuron B3 of buccal ganglia of Helix pomatia
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:38:00 GMT 2023
Edited
by admin
on Sat Dec 16 17:38:00 GMT 2023
Record UNII
RUA6CWU76G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALPROMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
valpromide [INN]
Common Name English
VALPROIC ACID IMPURITY F [EP IMPURITY]
Common Name English
VALPROMIDE [MI]
Common Name English
Valpromide [WHO-DD]
Common Name English
2-PROPYLVALERAMIDE
Systematic Name English
VALPROMIDE [MART.]
Common Name English
DEPAMIDE
Brand Name English
2-PROPYLPENTANAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
WHO-ATC N03AG02
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WHO-VATC QN03AG02
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
Code System Code Type Description
MERCK INDEX
m11370
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY Merck Index
FDA UNII
RUA6CWU76G
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
NCI_THESAURUS
C152822
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PRIMARY
DRUG CENTRAL
2804
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
WIKIPEDIA
VALPROMIDE
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
DRUG BANK
DB04165
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PRIMARY
EVMPD
SUB00016MIG
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PRIMARY
ChEMBL
CHEMBL93836
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PRIMARY
EPA CompTox
DTXSID1023734
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PRIMARY
PUBCHEM
71113
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
CAS
2430-27-5
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PRIMARY
SMS_ID
100000079069
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PRIMARY
INN
4365
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PRIMARY
ECHA (EC/EINECS)
219-394-2
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
CHEBI
74562
Created by admin on Sat Dec 16 17:38:01 GMT 2023 , Edited by admin on Sat Dec 16 17:38:01 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PARENT
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PARENT -> IMPURITY
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ACTIVE MOIETY