CGP 78608 (CHEBI:64061)

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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.

Supplier Information

Download	Molfile XML SDF

Formula

C11H13BrN3O5P

Net Charge

Average Mass

378.11600

Monoisotopic Mass

376.97762

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.

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

Registry Number	Type	Source
8227979	Reaxys Registry Number	Reaxys

Last Modified

01 March 2012