PEAQX: Difference between revisions
Appearance
Content deleted Content added
templated cites |
Entranced98 (talk | contribs) Adding local short description: "Chemical compound", overriding Wikidata description "pair of isomers" |
||
(4 intermediate revisions by 4 users not shown) | |||
Line 1: | Line 1: | ||
{{Short description|Chemical compound}} |
|||
{{Drugbox |
{{Drugbox |
||
| Verifiedfields = changed |
| Verifiedfields = changed |
||
Line 4: | Line 5: | ||
| verifiedrevid = 429827414 |
| verifiedrevid = 429827414 |
||
| IUPAC_name = ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid |
| IUPAC_name = ({[(1S)-1-(4-bromophenyl)ethyl]amino}-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl)phosphonic acid |
||
| image = PEAQX. |
| image = PEAQX.svg |
||
| width = 240 |
| width = 240 |
||
Line 35: | Line 36: | ||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
||
| DrugBank = |
| DrugBank = |
||
| UNII_Ref = {{fdacite|correct|FDA}} |
|||
| UNII = LE8K7M4APN |
|||
<!--Chemical data--> |
<!--Chemical data--> |
||
| C=17 | H=17 | Br=1 | N=3 | O=5 | P=1 |
| C=17 | H=17 | Br=1 | N=3 | O=5 | P=1 |
||
| molecular_weight = 454.211 g/mol |
|||
| synonyms = PEAQX, NVP-AAM077 |
| 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 |
| 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 |
||
Line 47: | Line 49: | ||
}} |
}} |
||
'''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 }}</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> |
'''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> |
||
== References == |
== References == |
Latest revision as of 12:21, 13 May 2023
Clinical data | |
---|---|
Other names | PEAQX, NVP-AAM077 |
Identifiers | |
| |
PubChem CID | |
ChemSpider | |
UNII | |
Chemical and physical data | |
Formula | C17H17BrN3O5P |
Molar mass | 454.217 g·mol−1 |
3D model (JSmol) | |
| |
| |
(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]
- ^ 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.
- ^ 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.