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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 since 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> Prodrugs were developed since the oral bioavailability of perzinfotel 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 16:47, 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 since the oral bioavailability of perzinfotel 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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