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'''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, although further development of this drug has been discontinued.<ref>http://adisinsight.springer.com/drugs/800009946</ref> '''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, although further development of this drug has been discontinued.<ref>http://adisinsight.springer.com/drugs/800009946</ref>

Prodrugs were developed due to the fact that the bioavailability of perzinfotel upon oral application is only around 3-5%.<ref name="BaudyButera2009">{{cite journal|last1=Baudy|first1=Reinhardt B.|last2=Butera|first2=John A.|last3=Abou-Gharbia|first3=Magid A.|last4=Chen|first4=Hong|last5=Harrison|first5=Boyd|last6=Jain|first6=Uday|last7=Magolda|first7=Ronald|last8=Sze|first8=Jean Y.|last9=Brandt|first9=Michael R.|last10=Cummons|first10=Terri A.|last11=Kowal|first11=Diane|last12=Pangalos|first12=Menelas N.|last13=Zupan|first13=Bojana|last14=Hoffmann|first14=Matthew|last15=May|first15=Michael|last16=Mugford|first16=Cheryl|last17=Kennedy|first17=Jeffrey|last18=Childers|first18=Wayne E.|title=Prodrugs of Perzinfotel with Improved Oral Bioavailability|journal=Journal of Medicinal Chemistry|volume=52|issue=3|year=2009|pages=771–778|issn=0022-2623|doi=10.1021/jm8011799}}</ref>
== References == == References ==
{{reflist}} {{reflist}}

Revision as of 16:44, 10 July 2016

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, although further development of this drug has been discontinued.

Prodrugs were developed due to the fact that the bioavailability of perzinfotel upon oral application is only around 3-5%.

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. http://adisinsight.springer.com/drugs/800009946
  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.
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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