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

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

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
[Cerebral edema with hyperammonemia in valpromide poisoning. Manifestation in an adult, of a partial deficit in type I carbamylphosphate synthetase].	1988 Nov 5	2974563
New CNS-active drugs which are second-generation valproic acid: can they lead to the development of a magic bullet?	2003 Apr	12644750
Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy.	2003 Aug	12948028
Mood-stabilizers: the archeology of the concept.	2003 Dec	14636369
Lupus-like syndrome and vasculitis induced by valpromide.	2003 Jan	12508420
[The Charles Bonnet syndrome: a case report and a brief review].	2003 Jan-Feb	12590373
Valproate induces replication-independent active DNA demethylation.	2003 Jul 25	12748177
Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site.	2003 Jun 2	12773375
Inhibition of histone deacetylase activity by valproic acid blocks adipogenesis.	2004 Apr 30	14985358
Valproate decreases inositol biosynthesis.	2004 Dec 1	15576064
Amidic modification of valproic acid reduces skeletal teratogenicity in mice.	2004 Feb	14991910
Valproate potentiates androgen biosynthesis in human ovarian theca cells.	2004 Feb	14576182
Characterization of the anticonvulsant profile of valpromide derivatives.	2004 Jul 15	15210153
[Valpromide, Valproic acid and removal of small intestine in the treatment of a chronic depression: a case report].	2004 Jul-Aug	15538315
Delayed toxicity following acute ingestion of valpromide.	2004 Mar	15119534
Polycomb homologs are involved in teratogenicity of valproic acid in mice.	2004 Nov	15523661
[Deep lactic acidosis after valproate self-poisoning].	2004 Oct	15501631
Identification of early-responsive genes correlated to valproic acid-induced neural tube defects in mice.	2005 Apr	15799026
Management of epilepsy in adults. Diagnosis guidelines.	2005 Dec	16382762
Mood stabilizer augmentation in apparently "unipolar" MDD: predictors of response in the naturalistic French national EPIDEP study.	2005 Feb	15708422
[Management of bipolar disorders].	2005 Mar 15	15895954
The role of histone acetylation in SMN gene expression.	2005 May 1	15772088
Histone deacetylases inhibition and tumor cells cytotoxicity by CNS-active VPA constitutional isomers and derivatives.	2005 May 15	15857614
[Valpromide poisoning associated with circulatory collapse].	2005 Nov-Dec	16555501
Induction of osteogenic differentiation of human mesenchymal stem cells by histone deacetylase inhibitors.	2005 Oct 15	16088945
Catalytic mechanism of limonene epoxide hydrolase, a theoretical study.	2005 Oct 19	16218628
Efficacy of antiepileptic isomers of valproic acid and valpromide in a rat model of neuropathic pain.	2005 Sep	15997234
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 antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver.	2006 Oct	16894351
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
Effect of valproic acid on radiation-induced DNA damage in euchromatic and heterochromatic compartments.	2008 Feb 15	18239454
Lipid peroxidation in women with epilepsy.	2008 Jan	19966978
[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
Effect of melatonin and melatonylvalpromide on beta-amyloid and neurofilaments in N2a cells.	2008 Jun	18231852
Evaluation of the enantioselective antiallodynic and pharmacokinetic profile of propylisopropylacetamide, a chiral isomer of valproic acid amide.	2008 Mar	18201732
[Neonatal Volkmann's syndrome].	2009 Nov	19917430
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
Histone deacetylase inhibitor valproic acid inhibits cancer cell proliferation via down-regulation of the alzheimer amyloid precursor protein.	2010 Apr 2	20145244
Metabolic activation capacity by primary hepatocytes expands the applicability of the embryonic stem cell test as alternative to experimental animal testing.	2010 Aug	20132877
Agomelatine: The evidence for its place in the treatment of depression.	2010 Jun 15	20694073
[Pharmacokinetics of biological tags in a case of acute valpromide self poisoning].	2010 Mar-Apr	20348051
[Therapeutic drug monitoring of valproate].	2010 May-Jun	20699076
Characterization of Human Huntington's Disease Cell Model from Induced Pluripotent Stem Cells.	2010 Oct 28	21037797
Inhibition of class II histone deacetylases in the spinal cord attenuates inflammatory hyperalgesia.	2010 Sep 7	20822541

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

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

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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