PEAQX: Difference between revisions
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| PubChem = |
| PubChem = 9868551 |
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| ChemSpiderID = 8044242 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| C=17 | H=17 | Br=1 | N=3 | O=5 | P=1 |
| C=17 | H=17 | Br=1 | N=3 | O=5 | P=1 |
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| molecular_weight = 454.211 g/mol |
| molecular_weight = 454.211 g/mol |
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| smiles = O=c2nc1c(nc2=O)cccc1C(P(O)(O)=O)NC(C)c3ccc(Br)cc3 |
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| synonyms = PEAQX, NVP-AAM077 |
| synonyms = PEAQX, NVP-AAM077 |
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| 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 |
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| InChI = 1/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 |
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| InChIKey = XXZGNAZRWCBSBK-WFVOFKTRBH |
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| 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 |
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| StdInChIKey = XXZGNAZRWCBSBK-WFVOFKTRSA-N |
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Revision as of 18:30, 10 December 2014
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| Clinical data | |
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| Other names | PEAQX, NVP-AAM077 |
| Identifiers | |
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| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C17H17BrN3O5P |
| Molar mass | 454.211 g/mol g·mol−1 |
| 3D model (JSmol) | |
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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
- ^ Frizelle PA, Chen PE, Wyllie DJ 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 2006 Sep;70(3):1022-32. PMID 16778008
- ^ 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