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CHEBI:64061 - CGP 78608

ChEBI IDCHEBI:64061
ChEBI NameCGP 78608
Stars
DefinitionA phosphonic acid in which the hydrogen attached to phosphorous is substituted by a 1-{[(7-bromo-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)methyl]amino}ethyl group. Potent and selective NMDA antagonist that acts through the glycine site (IC50 = 5 nM). Displays >500-fold selectivity over kainate and AMPA receptors (IC50 values are 2.7 and 3 μM respectively). Anticonvulsant in vivo following systemic administration.
Last Modified1 March 2012
SubmitterSteve
DownloadsMolfile
FormulaC11H13BrN3O5P
Net Charge0
Average Mass378.119
Monoisotopic Mass376.97762
SMILESC[C@@H](NCc1cc(Br)cc2nc(=O)c(=O)nc12)P(=O)(O)O
InChIInChI=1S/C11H13BrN3O5P/c1-5(21(18,19)20)13-4-6-2-7(12)3-8-9(6)15-11(17)10(16)14-8/h2-3,5,13H,4H2,1H3,(H,14,16)(H,15,17)(H2,18,19,20)/t5-/m0/s1
InChIKeyDPFHVUSPVHRVFL-YFKPBYRVSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
Application:
anticonvulsant  A drug used to prevent seizures or reduce their severity.
ChEBI Ontology
Outgoing Relation(s)
CGP 78608 (CHEBI:64061) has part CGP 78608(1+) (CHEBI:64066)
CGP 78608 (CHEBI:64061) has role anticonvulsant (CHEBI:35623)
CGP 78608 (CHEBI:64061) has role NMDA receptor antagonist (CHEBI:60643)
CGP 78608 (CHEBI:64061) is a organobromine compound (CHEBI:37141)
CGP 78608 (CHEBI:64061) is a phosphonic acids (CHEBI:26069)
CGP 78608 (CHEBI:64061) is a quinoxaline derivative (CHEBI:38771)
CGP 78608 (CHEBI:64061) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
[(1S)-1-{[(7-bromo-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)methyl]amino}ethyl]phosphonic acid
Manual XrefsDatabases
US6117873Patent
Registry NumbersSources
Reaxys:8227979Reaxys
Citations