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Details

Stereochemistry EPIMERIC
Molecular Formula C17H17BrN3O5P
Molecular Weight 454.212
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PEAQX

SMILES

C[C@H](NC(C1=C2NC(=O)C(=O)NC2=CC=C1)P(O)(O)=O)C3=CC=C(Br)C=C3

InChI

InChIKey=XXZGNAZRWCBSBK-WFVOFKTRSA-N
InChI=1S/C17H17BrN3O5P/c1-9(10-5-7-11(18)8-6-10)19-17(27(24,25)26)12-3-2-4-13-14(12)21-16(23)15(22)20-13/h2-9,17,19H,1H3,(H,20,22)(H,21,23)(H2,24,25,26)/t9-,17?/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H17BrN3O5P
Molecular Weight 454.212
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

PEAQX (NVP-AAM 077) is a potent and orally active NMDA antagonist with a 15-fold preference for human NMDA receptors with the 1A/2A(IC50=270 nM), rather than 1A/2B (29,600 nM). Animals treated with PCP or PEAQX on PN7, PN9, and PN11 showed a sensitized locomotor response to PCP challenge on PN28-PN35. PEAQX induced social suppression in rats.

CNS Activity

Curator's Comment: PEAQX induced social suppression in rats.

Originator

Curator's Comment: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
270.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition.
2002 Apr 8
Differential role of N-methyl-D-aspartate receptor subunits 2A and 2B in mediating phencyclidine-induced perinatal neuronal apoptosis and behavioral deficits.
2009 Nov 10
Low doses of the NMDA receptor antagonists, MK-801, PEAQX, and ifenprodil, induces social facilitation in adolescent male rats.
2013 Aug 1
The effects of an acute challenge with the NMDA receptor antagonists, MK-801, PEAQX, and ifenprodil, on social inhibition in adolescent and adult male rats.
2014 Apr
Patents

Sample Use Guides

Rats: 10, 20 or 40 mg/kg PEAQX (s.c.)
Route of Administration: Other
In “older” hippocampal rat neurons (13-16 DIV), ifenprodil (50uM) and PEAQX (5uM) applied separately only partly (45-55%) inhibited NMDA-induced increases in [Ca2+]c with IC50=0.29±0.14uM and 0.13±0.04uM, respectively. If applied simultaneously, even at lower concentrations, ifenprodil (1uM) and PEAQX (0.1uM) practically completely inhibited NMDA-induced increases in [Ca2+]c.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:28:54 GMT 2023
Edited
by admin
on Sat Dec 16 17:28:54 GMT 2023
Record UNII
LE8K7M4APN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PEAQX
Common Name English
PHOSPHONIC ACID, P-((((1S)-1-(4-BROMOPHENYL)ETHYL)AMINO)(1,2,3,4-TETRAHYDRO-2,3-DIOXO-5-QUINOXALINYL)METHYL)-
Systematic Name English
PHOSPHONIC ACID, ((((1S)-1-(4-BROMOPHENYL)ETHYL)AMINO)(1,2,3,4-TETRAHYDRO-2,3-DIOXO-5-QUINOXALINYL)METHYL)-
Systematic Name English
AAM 007
Common Name English
P-((((1S)-1-(4-BROMOPHENYL)ETHYL)AMINO)(1,2,3,4-TETRAHYDRO-2,3-DIOXO-5-QUINOXALINYL)METHYL)PHOSPHONIC ACID
Systematic Name English
((((S)-1-(4-BROMOPHENYL)ETHYL)AMINO)(2,3-DIOXO-1,2,3,4-TETRAHYDROQUINOXALIN-5-YL)METHYL)PHOSPHONIC ACID
Systematic Name English
(1RS,1'S)-PEAQX
Common Name English
Code System Code Type Description
PUBCHEM
9868551
Created by admin on Sat Dec 16 17:28:54 GMT 2023 , Edited by admin on Sat Dec 16 17:28:54 GMT 2023
PRIMARY
FDA UNII
LE8K7M4APN
Created by admin on Sat Dec 16 17:28:54 GMT 2023 , Edited by admin on Sat Dec 16 17:28:54 GMT 2023
PRIMARY
CAS
459836-30-7
Created by admin on Sat Dec 16 17:28:54 GMT 2023 , Edited by admin on Sat Dec 16 17:28:54 GMT 2023
PRIMARY
WIKIPEDIA
PEAQX
Created by admin on Sat Dec 16 17:28:54 GMT 2023 , Edited by admin on Sat Dec 16 17:28:54 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
the Ki of PEAQX revealed it only shows a 5 fold difference in affinity for GluN1/GluN2A vs. GluN1/GluN2B receptors. It is also a potent anticonvulsant in animal tests.
COMPETITIVE ANTAGONIST
TARGET -> INHIBITOR
the Ki of PEAQX revealed it only shows a 5 fold difference in affinity for GluN1/GluN2A vs. GluN1/GluN2B receptors. It is also a potent anticonvulsant in animal tests.
COMPETITIVE ANTAGONIST
TARGET -> INHIBITOR
COMPETITIVE ANTAGONIST