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Perzinfotel

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Title: Perzinfotel  
Author: World Heritage Encyclopedia
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Subject: Selfotel, Midafotel, Remacemide, Methoxyketamine, Aptiganel
Collection: 1,4-Diazepines, Nmda Receptor Antagonists, Phosphonic Acids, Quinones
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Perzinfotel

Perzinfotel
Systematic (IUPAC) name
2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethylphosphonic acid
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code None
PubChem
ChemSpider  N
UNII  YesY
KEGG  YesY
Chemical data
Formula C9H13N2O5P 
Mol. mass 260.184 g/mol
 N   

Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist.[1] It has neuroprotective effects and has been investigated for the treatment of stroke,[2] but lacks analgesic effects.[3] Nevertheless it shows a good safety profile compared to older drugs, and further research is ongoing.

Synthesis

References

  1. ^ 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
  2. ^ 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
  3. ^ 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
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