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| StdInChIKey = BDABGOLMYNHHTR-UHFFFAOYSA-N | StdInChIKey = BDABGOLMYNHHTR-UHFFFAOYSA-N
}} }}
'''Perzinfotel''' ('''EAA-090''') is a drug which acts as a potent ].<ref>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 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</ref> It has ] effects and has been investigated for the treatment of ],<ref>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-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</ref> but lacks ] effects.<ref>Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S. Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel 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</ref> Nevertheless it shows a good safety profile compared to older drugs, and further research is ongoing. '''Perzinfotel''' ('''EAA-090''') is a drug which acts as a potent ].<ref>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 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</ref> It has ] effects and has been investigated for the treatment of ],<ref>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-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</ref> but lacks ] effects.<ref>Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S. Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel 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</ref> Nevertheless it shows a good safety profile compared to older drugs, and further research is ongoing. To increase the low oral ] of Perzinfotel (3-5%), ] derivatives were synthesized and evaluated.<ref>{{Cite doi|10.1021/jm8011799}}</ref>
==Synthesis== ==Synthesis==

Revision as of 06:30, 8 January 2015

Pharmaceutical compound
Perzinfotel
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 2-(8,9-dioxo-2,6-diazabicyclonon-1(7)-en-2-yl)ethylphosphonic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.222.780 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N2O5P
Molar mass260.184 g/mol g·mol
3D model (JSmol)
SMILES
  • C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O
InChI
  • 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)
  • Key:BDABGOLMYNHHTR-UHFFFAOYSA-N
  (what is this?)  (verify)

Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist. It has neuroprotective effects and has been investigated for the treatment of stroke, but lacks analgesic effects. Nevertheless it shows a good safety profile compared to older drugs, and further research is ongoing. To increase the low oral bioavailability of Perzinfotel (3-5%), prodrug derivatives were synthesized and evaluated.

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 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-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 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
  4. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm8011799, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/jm8011799 instead.
Glutamate receptor modulators
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators
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