U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H20N2O2
Molecular Weight 200.278
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALROCEMIDE

SMILES

CCCC(CCC)C(=O)NCC(N)=O

InChI

InChIKey=RALGCAOVRLYSMA-UHFFFAOYSA-N
InChI=1S/C10H20N2O2/c1-3-5-8(6-4-2)10(14)12-7-9(11)13/h8H,3-7H2,1-2H3,(H2,11,13)(H,12,14)

HIDE SMILES / InChI
Valrocemide is an anticonvulsant agent which was under development by Teva and Acorda as a potential therapeutic for the treatment of epilepsy. Valrocemide is an N-valproyl derivative of GABAand glycine. It was found that 1 mM of valrocemide could drastically inhibit human brain crude homogenate MIP synthase activity. Furthermore, the mechanism of the effect of valrocemide was studied and results showed that valrocemide reduced the enzyme activity by an apparent competitive mode of inhibition. In October 2003, a phase II trial using valrocemide as an adjunct therapy in refractory epilepsy patients had been completed and phase III trials were being planned. Valrocemide was also being investigated for potential utility in the treatment of bipolar disorder and neuropathic pain. This compound was originally discovered by Yissum Research and Development Company of the Hebrew University of Jerusalem, then licensed and developed by Teva in collaboration with Acorda in 2003, then licensed to Shire the worldwide development, production and marketing rights in 2006. However, the development of Valrocemide was discontinued by Shire in 2009.

Approval Year

PubMed

PubMed

TitleDatePubMed
New CNS-active drugs which are second-generation valproic acid: can they lead to the development of a magic bullet?
2003 Apr

Sample Use Guides

After administration of single doses up to 4,000 mg and multiple daily doses between 250 and 1000 mg three times daily in healthy volunteers, valrocemide is absorbed rapidly.
Route of Administration: Oral
1 mM of valrocemide could drastically inhibit human brain crude homogenate MIP synthase activity.
Name Type Language
VALROCEMIDE
INN   USAN  
USAN   INN  
Official Name English
PENTANAMIDE, N-(2-AMINO-2-OXOETHYL)-2-PROPYL
Common Name English
N-(2-AMINO-2-OXOETHYL)-2-PROPYLPENTANAMIDE
Systematic Name English
TV-1901
Code English
N-(Carbamoylmethyl)-2-propylvaleramide
Systematic Name English
VALROCEMIDE [USAN]
Common Name English
valrocemide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:48:51 GMT 2023 , Edited by admin on Fri Dec 15 15:48:51 GMT 2023
Code System Code Type Description
DRUG BANK
DB06657
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PRIMARY
USAN
OO-58
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FDA UNII
1C7GO6OW7L
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EPA CompTox
DTXSID70238939
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SMS_ID
300000034457
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ChEMBL
CHEMBL471638
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NCI_THESAURUS
C87610
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INN
7756
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PUBCHEM
6918293
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CAS
92262-58-3
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