Clinical data
ATC code none
CAS Number 144912-63-0 YesY
PubChem (CID) 6918236
ChemSpider 5293443 N
KEGG D05447 YesY
ECHA InfoCard 100.222.780
Chemical and physical data
Formula C9H13N2O5P
Molar mass 260.184 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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, although further development of this drug has been discontinued.[4]

Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.[5]


  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
  5. Baudy, Reinhardt B.; Butera, John A.; Abou-Gharbia, Magid A.; Chen, Hong; Harrison, Boyd; Jain, Uday; Magolda, Ronald; Sze, Jean Y.; Brandt, Michael R.; Cummons, Terri A.; Kowal, Diane; Pangalos, Menelas N.; Zupan, Bojana; Hoffmann, Matthew; May, Michael; Mugford, Cheryl; Kennedy, Jeffrey; Childers, Wayne E. (2009). "Prodrugs of Perzinfotel with Improved Oral Bioavailability". Journal of Medicinal Chemistry. 52 (3): 771–778. doi:10.1021/jm8011799. ISSN 0022-2623.
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