SML0206
EAA-090
≥98% (HPLC)
Synonym(s):
P-[2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]-phosphonic acid, WAY-126090
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About This Item
Empirical Formula (Hill Notation):
C9H13N2O5P
CAS Number:
Molecular Weight:
260.18
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
assay
≥98% (HPLC)
form
powder
color
light yellow to yellow
solubility
H2O: ≥2 mg/mL
originator
Wyeth
storage temp.
2-8°C
SMILES string
OP(O)(=O)CCN1CCCNC2=C1C(=O)C2=O
InChI
1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16)
InChI key
BDABGOLMYNHHTR-UHFFFAOYSA-N
Application
EAA-090 was used to study the role of glutamate receptor-mediated signaling in the formation of filipodia and secondary dendrites in rat hippocampal neurons.
Biochem/physiol Actions
EAA-090 inhibits the binding of ligands to glutamate receptors and blocks NMDA-induced currents. It is neuroprotective against glutamate and ischemia-induced toxicity.
EAA-090 is a potent NMDA receptor antagonist with neuroprotective properties. In isoflurane-anesthetized dogs, EAA-090 reduces the minimum alveolar concentration (MAC) of isoflurane and increases systolic, mean, and diastolic arterial blood pressure.
NMDA antagonist
Features and Benefits
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 2 Oral
Storage Class
6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Frank Henle et al.
Naunyn-Schmiedeberg's archives of pharmacology, 385(2), 171-180 (2011-10-29)
GluN receptors are heteromers of obligatory GluN1 subunits and GluN2(A-D) subunits. In the present study, we addressed the question whether GluN2A and GluN2B subunits play distinct roles in the formation of filopodia and dendrites during the early development of hippocampal
Lucy Sun et al.
The Journal of pharmacology and experimental therapeutics, 310(2), 563-570 (2004-04-13)
Two novel N-methyl-d-aspartate (NMDA) antagonists with unique chemical structures, EAA-090 (2-[8,9-dioxo-2, 6-diazabicyclo[5.2.0]non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride), were compared with CGS-19755 (Selfotel) in ligand binding, electrophysiology, and neuroprotection assays. CGS-19755, EAA-090 and EAB-318 inhibited [(3)H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid binding to NMDA
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML0206-10MG | 04061832075150 |
| SML0206-50MG | 04061832260785 |