CHEBI:64061 - CGP 78608

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ChEBI Name CGP 78608
ChEBI ID CHEBI:64061
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H13BrN3O5P
Net Charge 0
Average Mass 378.11600
Monoisotopic Mass 376.978
InChI InChI=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
InChIKey DPFHVUSPVHRVFL-YFKPBYRVSA-N
SMILES C[C@@H](NCc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12)P(O)(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
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ChEBI Ontology
Outgoing 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 Xref Database
US6117873 Patent
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Registry Number Type Source
8227979 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15223384 PubMed citation Europe PMC
17405869 PubMed citation Europe PMC
19394327 PubMed citation Europe PMC
Last Modified
01 March 2012