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
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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28605109Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28605109
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24995528 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20636634 |
Primary | Unknown Approved UseUnknown |
||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20636634
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24995528
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 | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
1065
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 | |||
|
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 | ||
|
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 | |||
|
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
|
PRIMARY | |||
|
DTXSID40863333
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 | |||
|
100000079047
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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
|
PRIMARY | |||
|
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
|
PRIMARY | |||
|
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 |
ACTIVE MOIETY