Perzinfotel

Names

[ Name ]:
Perzinfotel

[Synonym ]:
2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-6-yl)ethylphosphonic acid

Biological Activity

[Description]:

Perzinfotel (EAA-090) is a potent, selective, and competitive NMDA receptor antagonist with neuroprotective effects. Perzinfotel (EAA-090) shows high affinity (IC50=30 nM) for the glutamate site[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

NMDA receptor[1]

[In Vitro]

Perzinfotel blocks NMDA-induced currents with an IC50 of 0.48 μM and glutamate-induced neurotoxicity with an IC50 of 1.6 μM[1].

[References]

[1]. Brandt MR, et al. Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel [EAA-090; [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity. J Pharmacol Exp Ther. 2005 Jun;313(3):1379-86.

[2]. Kinney WA, et al. Design and synthesis of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid(EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral alpha-amino acid bioisostere. J Med Chem. 1998 Jan 15;41(2):236-46.

Chemical & Physical Properties

[ Molecular Formula ]:
C₉H₁₃N₂O₅P

[ Molecular Weight ]:
260.18400

[ Exact Mass ]:
260.05600

[ PSA ]:
116.75000

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ RIDADR ]:
UN 2811 6.1 / PGIII

Articles

Characterization of two novel N-methyl-D-aspartate antagonists: 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).

J. Pharmacol. Exp. Ther. 310(2) , 563-70, (2004)

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-chlo...

Role of GluN2A and GluN2B subunits in the formation of filopodia and secondary dendrites in cultured hippocampal neurons.

Naunyn Schmiedebergs Arch. Pharmacol. 385(2) , 171-80, (2012)

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 format...