| Identification | Back Directory | [Name]
(S)-1-(2-AMINO-2-CARBOXYETHYL)-3-(2-CARBOXYBENZYL)PYRIMIDINE-2,4-DIONE | [CAS]
745055-91-8 | [Synonyms]
UBP 302
UBP302, PUBCHEM CID: 6420161
(S)-1-(2-AMINO-2-CARBOXYETHYL)-3-(2-CARBOXYBENZYL)PYRIMIDINE-2,4-DIONE
2-[[3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxopyrimidin-1-yl]methyl]benzoic acid
(αS)-α-amino-3-[(2-carboxyphenyl)methyl]-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
1(2H)-Pyrimidinepropanoic acid, α-amino-3-[(2-carboxyphenyl)methyl]-3,4-dihydro-2,4-dioxo-, (αS)- | [Molecular Formula]
C15H15N3O6 | [MDL Number]
MFCD06411607 | [MOL File]
745055-91-8.mol | [Molecular Weight]
333.3 |
| Chemical Properties | Back Directory | [Melting point ]
207.9-208.5 °C (decomp)(Solv: water (7732-18-5)) | [Boiling point ]
603.0±65.0 °C(Predicted) | [density ]
1.525±0.06 g/cm3(Predicted) | [storage temp. ]
Store at RT | [solubility ]
DMSO: ≥5mg/mL at 60°C (with warming for 5 minutes) | [form ]
powder | [pka]
2.12±0.10(Predicted) | [color ]
white to off-white |
| Hazard Information | Back Directory | [Description]
UBP 302 is an antagonist of glutamate receptor 5 (GluR5) subunit-containing kainate receptors that inhibits kainate-induced responses in isolated rat dorsal roots (Kd = 402 nM). In vitro, UBP 302 inhibits gamma frequency oscillations in the rat basolateral amygdala at a concentration of 25 μM, and blocks kainate receptor signaling in layer III neurons within the mouse medial entorhinal cortex at 20 μM, abrogating the intense synaptic activity characteristic of the Up state of cortical slow oscillation. In vivo, UBP 302 (250 mg/kg) significantly reduces seizure severity in a rat model of soman-induced status epilepticus. | [Uses]
UBP 302 is a potent and selective GLUK5 receptor antagonist. | [Biological Activity]
Selective and potent GLU K5 (GluR5)-subunit containing kainate receptor antagonist (apparent K D = 402 nM); active enantiomer of UBP 296 ((RS)-1-(2-Amino-2-carboxyethyl)-3-(2-carboxybenzyl)pyrimidine-2,4-dione ). Displays ~ 260-fold selectivity over AMPA receptors. UBP 296 displays ~ 90-fold selectivity over recombinant human GLU K6 - and GLU K2 -containing kainate receptors, has little or no action at NMDA or group I mGlu receptors and selectively blocks kainate receptor-mediated LTP induction in rat hippocampal mossy fibres. | [storage]
Room temperature |
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