VALPROMIDE

Possibly Marketed Outside US

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 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bipolar disorder, manic phase 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3131112	Primary		Approved 8583	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.

C_max

Value	Dose	Co-administered	Analyte	Population
75 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6440792/	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:		VALPROIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
82 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6440792/	900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered:		VALPROIC ACID serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.84 h REVIEW https://www.sciencedirect.com/science/article/abs/pii/0378517385902194\|https://pubmed.ncbi.nlm.nih.gov/2029804/	300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered:		VALPROMIDE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
18 g single, oral Overdose Dose: 18 g Route: oral Route: single Dose: 18 g Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	Disc. AE: Drowsiness, Coma... AEs leading to discontinuation/dose reduction: Drowsiness Coma Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/
36 g single, oral Overdose Dose: 36 g Route: oral Route: single Dose: 36 g Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	Disc. AE: Coma... AEs leading to discontinuation/dose reduction: Coma Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/
600 mg 2 times / day multiple, oral Studied dose Dose: 600 mg, 2 times / day Route: oral Route: multiple Dose: 600 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11112935/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/11112935/	Sources: https://pubmed.ncbi.nlm.nih.gov/11112935/

AEs

AE	Significance	Dose	Population
Coma	Disc. AE	18 g single, oral Overdose Dose: 18 g Route: oral Route: single Dose: 18 g Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/
Drowsiness	Disc. AE	18 g single, oral Overdose Dose: 18 g Route: oral Route: single Dose: 18 g Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/
Coma	Disc. AE	36 g single, oral Overdose Dose: 36 g Route: oral Route: single Dose: 36 g Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15119534/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71113#section=BioAssay-Results Page: 23.0	no

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71113#section=BioAssay-Results Page: 28.0	no
CYP2D6 1388	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71113#section=BioAssay-Results Page: 28.0	no
CYP3A4 1946	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71113#section=BioAssay-Results Page: 28.0	no
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/71113#section=BioAssay-Results Page: 26 \| 28	no

PubMed

Title	Date	PubMed
Characterization of Human Huntington's Disease Cell Model from Induced Pluripotent Stem Cells.	2010-10-28	21037797
Inhibition of class II histone deacetylases in the spinal cord attenuates inflammatory hyperalgesia.	2010-09-07	20822541
Metabolic activation capacity by primary hepatocytes expands the applicability of the embryonic stem cell test as alternative to experimental animal testing.	2010-08	20132877
Agomelatine: The evidence for its place in the treatment of depression.	2010-06-15	20694073
Histone deacetylase inhibitor valproic acid inhibits cancer cell proliferation via down-regulation of the alzheimer amyloid precursor protein.	2010-04-02	20145244
[Pharmacokinetics of biological tags in a case of acute valpromide self poisoning].	2010-03-30	20348051
[Therapeutic drug monitoring of valproate].	2010-02-22	20699076
[Neonatal Volkmann's syndrome].	2009-11	19917430
Valproic acid induces functional heat-shock protein 70 via Class I histone deacetylase inhibition in cortical neurons: a potential role of Sp1 acetylation.	2009-11	19765194
Application of a metabolizing system as an adjunct to the rat whole embryo culture.	2008-08	18514478
[Effects of acupuncture under guidance of qi street theory on endocrine function in the patient of epilepsy].	2008-07	18678157
Valproic acid extends Caenorhabditis elegans lifespan.	2008-06	18248662
Effect of melatonin and melatonylvalpromide on beta-amyloid and neurofilaments in N2a cells.	2008-06	18231852
Evaluation of the enantioselective antiallodynic and pharmacokinetic profile of propylisopropylacetamide, a chiral isomer of valproic acid amide.	2008-03	18201732
Effect of valproic acid on radiation-induced DNA damage in euchromatic and heterochromatic compartments.	2008-02-15	18239454
Modifications of antiepileptic drugs for improved tolerability and efficacy.	2008-02-14	19787095
Lipid peroxidation in women with epilepsy.	2008-01	19966978
Acute and long-term treatment of mania.	2008	18689287
The effectiveness of anticonvulsants in psychiatric disorders.	2008	18472486
Agomelatine adjunctive therapy for acute bipolar depression: preliminary open data.	2007-09	17845278
The effects of central nervous system-active valproic acid constitutional isomers, cyclopropyl analogs, and amide derivatives on neuronal growth cone behavior.	2007-03	17167030
The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver.	2006-10	16894351
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.	2006-04	16415118
[Valpromide poisoning associated with circulatory collapse].	2006-03-25	16555501
Management of epilepsy in adults. Diagnosis guidelines.	2005-12	16382762
Catalytic mechanism of limonene epoxide hydrolase, a theoretical study.	2005-10-19	16218628
Induction of osteogenic differentiation of human mesenchymal stem cells by histone deacetylase inhibitors.	2005-10-15	16088945
Efficacy of antiepileptic isomers of valproic acid and valpromide in a rat model of neuropathic pain.	2005-09	15997234
Histone deacetylases inhibition and tumor cells cytotoxicity by CNS-active VPA constitutional isomers and derivatives.	2005-05-15	15857614
The role of histone acetylation in SMN gene expression.	2005-05-01	15772088
Identification of early-responsive genes correlated to valproic acid-induced neural tube defects in mice.	2005-04	15799026
[Management of bipolar disorders].	2005-03-15	15895954
Mood stabilizer augmentation in apparently "unipolar" MDD: predictors of response in the naturalistic French national EPIDEP study.	2005-02	15708422
Valproate decreases inositol biosynthesis.	2004-12-01	15576064
[Valpromide, Valproic acid and removal of small intestine in the treatment of a chronic depression: a case report].	2004-11-13	15538315
Polycomb homologs are involved in teratogenicity of valproic acid in mice.	2004-11	15523661
[Deep lactic acidosis after valproate self-poisoning].	2004-10	15501631
Characterization of the anticonvulsant profile of valpromide derivatives.	2004-07-15	15210153
Inhibition of histone deacetylase activity by valproic acid blocks adipogenesis.	2004-04-30	14985358
Delayed toxicity following acute ingestion of valpromide.	2004-03	15119534
Amidic modification of valproic acid reduces skeletal teratogenicity in mice.	2004-02	14991910
Valproate potentiates androgen biosynthesis in human ovarian theca cells.	2004-02	14576182
Mood-stabilizers: the archeology of the concept.	2003-12	14636369
Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy.	2003-08	12948028
Valproate induces replication-independent active DNA demethylation.	2003-07-25	12748177
Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site.	2003-06-02	12773375
New CNS-active drugs which are second-generation valproic acid: can they lead to the development of a magic bullet?	2003-04	12644750
[The Charles Bonnet syndrome: a case report and a brief review].	2003-02-19	12590373
Lupus-like syndrome and vasculitis induced by valpromide.	2003-01	12508420
[Cerebral edema with hyperammonemia in valpromide poisoning. Manifestation in an adult, of a partial deficit in type I carbamylphosphate synthetase].	1988-11-05	2974563

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 `Wed Apr 02 09:23:57 GMT 2025` Edited by `admin` on `Wed Apr 02 09:23:57 GMT 2025`
Record UNII	RUA6CWU76G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEPAMIDE

Preferred Name

English

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

2-PROPYLPENTANAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C264