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Details

Stereochemistry MIXED
Molecular Formula C8H17NO
Molecular Weight 143.2267
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALNOCTAMIDE

SMILES

CCC(C)C(CC)C(N)=O

InChI

InChIKey=QRCJOCOSPZMDJY-UHFFFAOYSA-N
InChI=1S/C8H17NO/c1-4-6(3)7(5-2)8(9)10/h6-7H,4-5H2,1-3H3,(H2,9,10)

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB13099 | https://www.ncbi.nlm.nih.gov/pubmed/12948028 | https://www.ncbi.nlm.nih.gov/pubmed/20636634 | https://www.ncbi.nlm.nih.gov/pubmed/24001086

Valnoctamide is a valproic acid derivative associated with a decreased risk for congenital abnormalities and developed by Beersheva Mental Health Center for treatment mania. Valnoctamide has been marketed as an anxiolytic and sedative in several European countries (as Nirvanil), including Italy, Holland, and Switzerland, until the year 2000 but was not actively promoted as an anticonvulsant. It was marketed in the U.S. as Axiquel by McNeil Laboratories in the 1970s. In mice, valnoctamide has been shown to be distinctly less teratogenic than valproic acid. Injection of 3 mkmol ⁄ kg at day 8 of gestation produced only 1% exencephaly (as compared to 0–1% in control mice and 53% in valproate-treated mice). Embryolethality rates showed similar results: 52% with valproate versus 5% in the controls and 2% with valnoctamide. Valnoctamide's patent is expired, and it is not the property of any major pharmaceutical company. Valnoctamide has potential as a therapy in epilepsy including status epilepticus (SE) and neuropathic pain and is currently being developed for the treatment of mania and Schizoaffective Disorder. In clinical trials, Valnoctamide was well tolerated but lacked efficacy in the treatment of symptoms in patients with acute mania.

Originator

Sources: Compt. rend. acad. sci. (U. R. S. S.) [N. S.] Volume 2, Pages21-3(in German 23-5), Journal, 1934

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy.
2000 Nov
Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy.
2003 Aug
Amidic modification of valproic acid reduces skeletal teratogenicity in mice.
2004 Feb
Polycomb homologs are involved in teratogenicity of valproic acid in mice.
2004 Nov
Identification of early-responsive genes correlated to valproic acid-induced neural tube defects in mice.
2005 Apr
Efficacy of antiepileptic isomers of valproic acid and valpromide in a rat model of neuropathic pain.
2005 Sep
Diverse mechanisms of antiepileptic drugs in the development pipeline.
2006 Jun
Effect of valproate derivatives on human brain myo-inositol-1-phosphate (MIP) synthase activity and amphetamine-induced rearing.
2007 Jul-Aug
Modifications of antiepileptic drugs for improved tolerability and efficacy.
2008 Feb 14
Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X).
2010 Dec
Valnoctamide as a valproate substitute with low teratogenic potential in mania: a double-blind, controlled, add-on clinical trial.
2010 Jun
Evaluation of the antiallodynic, teratogenic and pharmacokinetic profile of stereoisomers of valnoctamide, an amide derivative of a chiral isomer of valproic acid.
2010 Jun
Patents

Patents

Sample Use Guides

600 mg ⁄ day (200 mg three times daily) and increased to 1200 mg (400 mg three times daily) after four days. Each patient received valnoctamideor for five weeks
Route of Administration: Oral
Whole-cell recordings of mIPSCs were obtained by voltage clamping the cell at −70 mV (with series resistance compensation) while blocking excitatory currents with 3 mM kynurenic acid (Sigma-Aldrich, St. Louis, MO, USA) and Na+ channel-dependent release with 1 μM TTX (Abcam, Cambridge, UK). Following a 4-min baseline, perfusion solution was switched to an identical solution containing 1 mM valnoctamide (VCD). Drug was applied for 10 min and then washed out in normal recording solution for another 10 min. Flumazenil (FMZ) competition and diazepam (DZP) occlusion experiments were conducted similarly, with the first perfusion change to 500 μM VCD followed by 500 μM VCD + 10 μM FMZ or 1 μM DZP followed by 1 μM DZP + 1 mM VCD, respectively. FMZ and DZP were purchased from Tocris Bioscience (Bristol, UK) and VCD was purchased from Santa Cruz Biotechnology (Dallas, TX, USA). These drugs were dissolved in DMSO at stock concentrations of 1 M (VCD), 10 mM (FMZ and DZP). The final concentration of DMSO then ranged from 0.05–0.2% and was kept constant throughout each experiment.
Name Type Language
VALNOCTAMIDE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
2-ETHYL-3-METHYL-PENTANAMIDE
Systematic Name English
valnoctamide [INN]
Common Name English
Valnoctamide [WHO-DD]
Common Name English
VALNOCTAMIDE [USAN]
Common Name English
MCN-X-181
Code English
VALNOCTAMIDE [MI]
Common Name English
AXIQUEL
Brand Name English
NSC-34092
Code English
NSC-32363
Code English
VALNOCTAMIDE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N05CM13
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
WHO-VATC QN05CM13
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
Code System Code Type Description
FDA UNII
3O25NRX9YG
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
NCI_THESAURUS
C152818
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
DRUG CENTRAL
2802
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
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INN
1065
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MERCK INDEX
m11368
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY Merck Index
EVMPD
SUB00010MIG
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
WIKIPEDIA
VALNOCTAMIDE
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
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EPA CompTox
DTXSID40863333
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SMS_ID
100000079047
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PRIMARY
CAS
4171-13-5
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
NSC
34092
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
NSC
32363
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
224-033-7
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1075733
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY
PUBCHEM
20140
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
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MESH
C045179
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
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DRUG BANK
DB13099
Created by admin on Fri Dec 15 16:50:38 GMT 2023 , Edited by admin on Fri Dec 15 16:50:38 GMT 2023
PRIMARY