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{{Short description|Chemical compound}}
{{drugbox |
{{Drugbox
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| IUPAC_name = ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid
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| image = PEAQX.png
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| width = 240
| verifiedrevid = 429827414
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| CAS_number =
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| IUPAC_name = ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid
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| synonyms = PEAQX
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| image = PEAQX.svg
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| ATC_prefix =
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| width = 240
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| ATC_suffix =
| PubChem =
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| DrugBank =
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| C = 17 | H = 17 | Br = 1 | N = 3 | O = 5 | P = 1
| molecular_weight = 454.211 g/mol
| smiles = O=c2nc1c(nc2=O)cccc1C(P(O)(O)=O)NC(C)c3ccc(Br)cc3
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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<!--Clinical data-->
'''PEAQX''' is a competitive [[antagonist (pharmacology)|antagonist]] at the [[NMDA receptor]]. It is subtype-selective, with a 100x selectivity for NMDA receptors composed of 1A/2A subunits vs the 1A/2B subunit composition. It is also a potent [[anticonvulsant]] in animal tests.<ref>Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M. 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. ''Bioorganic and Medicinal Chemistry Letters''. 2002 Apr 8;12(7):1099-102. PMID 11909726</ref>
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| legal_CA =
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| legal_UK =
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| legal_US =
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<!--Pharmacokinetic data-->
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<!--Identifiers-->
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| CAS_number = 459836-30-7
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| ATC_prefix =
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| ATC_suffix =
| PubChem = 9868551
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8044242
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LE8K7M4APN
| ChEMBL = 273636

<!--Chemical data-->
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| C=17 | H=17 | Br=1 | N=3 | O=5 | P=1
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| synonyms = PEAQX, NVP-AAM077
| smiles = C[C@@H](C1=CC=C(C=C1)Br)NC(C2=C3C(=CC=C2)N=C(C(=N3)O)O)P(=O)(O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = XXZGNAZRWCBSBK-WFVOFKTRSA-N
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}}


'''PEAQX''' is a competitive [[antagonist (pharmacology)|antagonist]] at the [[NMDA receptor]]. Although originally described as 100-fold selective for GluN1/GluN2A receptors vs. GluN1/GluN2B receptors, more detailed studies<ref>{{cite journal | vauthors = Frizelle PA, Chen PE, Wyllie DJ | title = Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission | journal = Molecular Pharmacology | volume = 70 | issue = 3 | pages = 1022–32 | date = September 2006 | pmid = 16778008 | doi = 10.1124/mol.106.024042 | s2cid = 14304805 }}</ref> of 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.<ref>{{cite journal | vauthors = Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M | title = 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition | journal = Bioorganic & Medicinal Chemistry Letters | volume = 12 | issue = 7 | pages = 1099–102 | date = April 2002 | pmid = 11909726 | doi = 10.1016/s0960-894x(02)00074-4 }}</ref>
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==References==
<references/>


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== References ==
{{Glutamate_receptor_ligands}}
{{reflist}}


{{Ionotropic glutamate receptor modulators}}


[[Category:NMDA receptor antagonists]]
[[Category:NMDA receptor antagonists]]
[[Category:Organobromides]]
[[Category:4-Bromophenyl compounds]]
[[Category:Quinoxalines]]
[[Category:Quinoxalines]]
[[Category:Lactams]]
[[Category:Phosphonic acids]]

Latest revision as of 05:29, 23 September 2024

PEAQX
Clinical data
Other namesPEAQX, NVP-AAM077
Identifiers
  • ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC17H17BrN3O5P
Molar mass454.217 g·mol−1
3D model (JSmol)
  • C[C@@H](C1=CC=C(C=C1)Br)NC(C2=C3C(=CC=C2)N=C(C(=N3)O)O)P(=O)(O)O
  • 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 ☒N
  • Key:XXZGNAZRWCBSBK-WFVOFKTRSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

PEAQX is a competitive antagonist at the NMDA receptor. Although originally described as 100-fold selective for GluN1/GluN2A receptors vs. GluN1/GluN2B receptors, more detailed studies[1] of 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.[2]

References

[edit]
  1. ^ Frizelle PA, Chen PE, Wyllie DJ (September 2006). "Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission". Molecular Pharmacology. 70 (3): 1022–32. doi:10.1124/mol.106.024042. PMID 16778008. S2CID 14304805.
  2. ^ Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M (April 2002). "5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition". Bioorganic & Medicinal Chemistry Letters. 12 (7): 1099–102. doi:10.1016/s0960-894x(02)00074-4. PMID 11909726.
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