VALPROMIDE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3131112 | http://agence-prd.ansm.sante.fr/php/ecodex/rcp/R0254149.htm | https://www.drugs.com/international/valpromide.html

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
synaptic transmission, GABAergic 10 Target ID: GO:0051932 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3131112 \| http://agence-prd.ansm.sante.fr/php/ecodex/rcp/R0254149.htm	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder, manic phase 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3131112	Primary		Approved 8429	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

Title	Date	PubMed
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.	2000 Nov	11205735
Valpromide increases amplitude of heart rate circadian rhythm in remitted bipolar and unipolar disorders. A placebo-controlled study.	2000 Nov	11112935
Clonic seizure associated with high clozapine plasma level.	2001 Spring	11449038
Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy.	2003 Aug	12948028
Lupus-like syndrome and vasculitis induced by valpromide.	2003 Jan	12508420
Valproate potentiates androgen biosynthesis in human ovarian theca cells.	2004 Feb	14576182
Characterization of the anticonvulsant profile of valpromide derivatives.	2004 Jul 15	15210153
Polycomb homologs are involved in teratogenicity of valproic acid in mice.	2004 Nov	15523661
[Deep lactic acidosis after valproate self-poisoning].	2004 Oct	15501631
The role of histone acetylation in SMN gene expression.	2005 May 1	15772088
[Valpromide poisoning associated with circulatory collapse].	2005 Nov-Dec	16555501
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	16415118
The effects of central nervous system-active valproic acid constitutional isomers, cyclopropyl analogs, and amide derivatives on neuronal growth cone behavior.	2007 Mar	17167030
Agomelatine adjunctive therapy for acute bipolar depression: preliminary open data.	2007 Sep	17845278
Acute and long-term treatment of mania.	2008	18689287
The effectiveness of anticonvulsants in psychiatric disorders.	2008	18472486
Application of a metabolizing system as an adjunct to the rat whole embryo culture.	2008 Aug	18514478
Modifications of antiepileptic drugs for improved tolerability and efficacy.	2008 Feb 14	19787095
[Effects of acupuncture under guidance of qi street theory on endocrine function in the patient of epilepsy].	2008 Jul	18678157
Valproic acid extends Caenorhabditis elegans lifespan.	2008 Jun	18248662
Evaluation of the enantioselective antiallodynic and pharmacokinetic profile of propylisopropylacetamide, a chiral isomer of valproic acid amide.	2008 Mar	18201732
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	19765194

Patents

Sample Use Guides

In Vivo Use Guide

Recommended initial dose 750 mg per day

Route of Administration: Oral

In Vitro Use Guide

1 mM valpromide affects epileptiform activities of neuron B3 of buccal ganglia of Helix pomatia

Name

Type

Language

VALPROMIDE

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