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Revision as of 13:53, 25 November 2016 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{infobox_drug}} (changes to verified and watched fields) per Chem/infobox_drug validation (report errors or bugs)← Previous edit Revision as of 16:40, 9 April 2017 edit undoRjwilmsi (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers932,185 editsm Journal cites:, added 3 DOIs, added 1 PMID, templated 1 journal cites using AWB (12150)Next edit →
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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, 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>{{cite journal | pmid = 9457246 | doi=10.1021/jm970504g | volume=41 | title=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 | date=January 1998 | journal=J. Med. Chem. | pages=236–46 | last1 = Kinney | first1 = WA | last2 = Abou-Gharbia | first2 = M | last3 = Garrison | first3 = DT | display-authors = 3 | last4 = et al}}</ref> It has ] effects and has been investigated for the treatment of ],<ref>{{cite journal | last1 = Sun | first1 = L | last2 = Chiu | first2 = D | last3 = Kowal | first3 = D | last4 = Simon | first4 = R | last5 = Smeyne | first5 = M | last6 = Zukin | first6 = RS | last7 = Olney | first7 = J | last8 = Baudy | first8 = R | last9 = Lin | first9 = S | date = Aug 2004 | title = 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) | url = | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 310 | issue = 2| pages = 563–70 | doi = 10.1124/jpet.104.066092 | pmid = 15075380 }}</ref> but lacks ] effects.<ref>{{cite journal | pmid = 15764736 | doi=10.1124/jpet.105.084467 | volume=313 | title=Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity | date=June 2005 | journal=J. Pharmacol. Exp. Ther. | pages=1379–86 | last1 = Brandt | first1 = MR | last2 = Cummons | first2 = TA | last3 = Potestio | first3 = L | last4 = Sukoff | first4 = SJ | last5 = Rosenzweig-Lipson | first5 = S}}</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 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|pmid=19146418}}</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}}
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] ]
] ]



{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}

Revision as of 16:40, 9 April 2017

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; et al. (January 1998). "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". J. Med. Chem. 41: 236–46. doi:10.1021/jm970504g. PMID 9457246. {{cite journal}}: Explicit use of et al. in: |last4= (help)
  2. Sun, L; Chiu, D; Kowal, D; Simon, R; Smeyne, M; Zukin, RS; Olney, J; Baudy, R; Lin, S (Aug 2004). "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. 310 (2): 563–70. doi:10.1124/jpet.104.066092. PMID 15075380.
  3. Brandt, MR; Cummons, TA; Potestio, L; Sukoff, SJ; Rosenzweig-Lipson, S (June 2005). "Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity". J. Pharmacol. Exp. Ther. 313: 1379–86. doi:10.1124/jpet.105.084467. 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. PMID 19146418.
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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