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Perzinfotel

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Perzinfotel
Clinical data
ATC code
  • none
Identifiers
  • 2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethylphosphonic acid
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard100.222.780Edit this at Wikidata
Chemical and physical data
FormulaC9H13N2O5P
Molar mass260.186 g·mol−1
3D model (JSmol)
  • C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)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) ☒N
  • Key:BDABGOLMYNHHTR-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Perzinfotel (EAA-090) is a drug which acts as a potentNMDA antagonist.[1] It hasneuroprotective effects and has been investigated for the treatment ofstroke,[2] but lacksanalgesic 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]

References

[edit]
  1. ^Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, et al. (January 1998). "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.41 (2):236–46.doi:10.1021/jm970504g.PMID 9457246.
  2. ^Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S (August 2004). "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)".The Journal of Pharmacology and Experimental Therapeutics.310 (2):563–70.doi:10.1124/jpet.104.066092.PMID 15075380.S2CID 25505657.
  3. ^Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S (June 2005). "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".The Journal of Pharmacology and Experimental Therapeutics.313 (3):1379–86.doi:10.1124/jpet.105.084467.PMID 15764736.S2CID 12989500.
  4. ^"Perzinfotel".Adis International Ltd. Springer Nature Switzerland AG.
  5. ^Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, et al. (February 2009). "Prodrugs of perzinfotel with improved oral bioavailability".Journal of Medicinal Chemistry.52 (3):771–8.doi:10.1021/jm8011799.PMID 19146418.
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