Perzinfotel

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


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CAS_number= 144912-63-0
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PubChem= 6918236
DrugBank=
C=9 | H=13 | N=2 | O=5 | P=1
molecular_weight = 260.184 g/mol
smiles = C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O
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Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist. [Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, Miller TL, Tasse RP, Zaleska MM, Moyer JA. 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. "Journal of Medicinal Chemistry". 1998 Jan 15;41(2):236-46. PMID 9457246] It has neuroprotective effects and has been investigated for the treatment of stroke, [Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S. 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). "Journal of Pharmacology and Experimental Therapeutics". 2004 Aug;310(2):563-70. PMID 15075380] but lacks analgesic effects. [Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S. 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. "Journal of Pharmacology and Experimental Therapeutics". 2005 Jun;313(3):1379-86. PMID 15764736] Nevertheless it shows a good safety profile compared to older drugs, and further research is ongoing.

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