ISOVALERAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H11NO
Molecular Weight	101.1469
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CC(N)=O

InChI

InChIKey=SANOUVWGPVYVAV-UHFFFAOYSA-N

InChI=1S/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7)

HIDE SMILES / InChI

Molecular Formula	C5H11NO
Molecular Weight	101.1469
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00172094 | https://www.ncbi.nlm.nih.gov/pubmed/20890571

Isovaleramide (also known as NPS 1776) is one of the active anticonvulsant constituents of Valeriana pavonii, it was suggested, isovaleramide can be a positive allosteric modulator of the GABAA receptor. This drug was studied in clinical trials for the treatment of A migraine, epilepsy and some others CNS disorders, but these studies were discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20890571	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine headache 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00172094	Primary		Phase II 1132	Unknown Approved Use Unknown
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16732716	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RMF	https://www.1pchem.com/search?query=1P003RMF
A2B Chem	AB74967	http://a2bchem.com/prod/AB74967
AK Scientific	J10746	https://aksci.com/item_detail.php?cat=J10746
AK Scientific	X0346	https://aksci.com/item_detail.php?cat=X0346
AbovChem LLC	HY-B1229	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-B1229
ApexBio Technology	B1775	https://www.apexbt.com/catalogsearch/result/?q=B1775
Apollo Scientific	OR22499	http://www.apolloscientific.co.uk/chemical_results.php?qstext=OR22499&product_group=%25&search_fieldname=header_search
AstaTech	C75541	http://astatechinc.com/CPSResult.php?CRNO=C75541
BOC Sciences	541-46-8	http://www.bocsci.com/description.asp?cas=541-46-8
Chemspace	CSC000162204	https://chem-space.com/CSC000162204
Enamine	BBV-52988611	http://www.enaminestore.com/catalog/BBV-52988611
Enamine	PV-001820522028	https://www.enaminestore.com/blog/real/PV-001820522028/
Fluorochem	342138	http://www.fluorochem.co.uk/Products/Product?code=342138
Hairui	HR109732	http://www.hairuichem.com/en/product/search.do?q=HR109732
KeyOrganics	AS-14001	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-14001
Lab Network	LN00222516	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00222516
Lab Network	LN01325285	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01325285
Matrix Scientific	172439	http://www.matrixscientific.com/172439.html
MolPort	MolPort-000-142-044	https://www.molport.com/shop/molecule-link/MolPort-000-142-044
Molnova	M14938	https://www.molnova.com/en/serch-list.html?keywords=M14938
MuseChem	A000400	https://www.musechem.com/product/A000400.html
Princeton BioMolecular Research	OSSL_789699	http://www.princetonbio.com/order_online?common_id=OSSL_789699
Ryan Scientific	Dimethyl_sulfoxide	https://ryansci.com/products?q=Dimethyl_sulfoxide&list_q=&search_type=exact
Selleck Chemicals	S4116	http://www.selleckchem.com/search.html?searchDTO.searchParam=S4116
ShangHai Biochempartner	BCP05941	http://www.biochempartner.com/search_BCP05941
SynQuest	4148-1-Y7	http://www.synquestlabs.com/search-result.html?q=4148-1-Y7
SynQuest	65891	http://www.synquestlabs.com/search-result.html?q=65891
TargetMol	T0361	https://www.targetmol.com/search?keyword=T0361
Tetrahedron	TS31557	http://www.thsci.com/search.do?q=TS31557
TimTec	SBB028167	http://www.echemstore.com/catalogsearch/result/?q=SBB028167
TimTec	ST45373391	http://www.echemstore.com/catalogsearch/result/?q=ST45373391
Wonderchem	WD06BC5	http://www.wonder-chem.com/search.html?text=WD06BC5
eMolecules	725480	https://orderbb.emolecules.com/search/#?query=725480
eNovation Chemicals	D765948	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D765948&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-7790849976	https://mcule.com/MCULE-7790849976/

PubMed

Title	Date	PubMed
Insight to structural subsite recognition in plant thiol protease-inhibitor complexes : understanding the basis of differential inhibition and the role of water.	2001	11602025
New antiepileptic drugs that are second generation to existing antiepileptic drugs.	2006 Jun	16732716
Diverse mechanisms of antiepileptic drugs in the development pipeline.	2006 Jun	16621450
[Isovaleramide, an anticonvulsant molecule isolated from Valeriana pavonii].	2010 Apr-Jun	20890571

Patents

Sample Use Guides

In Vivo Use Guide

single oral dose 400 mg

Route of Administration: Oral

In Vitro Use Guide

isovaleramide (300 µM) exhibited a 42% of inhibition of the binding of ³H-FNZ to its sites.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:54:59 UTC 2023` Edited by `admin` on `Fri Dec 15 15:54:59 UTC 2023`
Record UNII	9CP4KB634M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOVALERAMIDE

Official Name

English

ISOVALERAMIDE [USAN]

Common Name

English

3-Methylbutanamide

Systematic Name

English

BUTANAMIDE, 3-METHYL-

Systematic Name

English

ISOVALERAMIDE [MI]

Common Name

English

NFS1776

Code

English

NSC-402555

Code

English

NFS-1776

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197