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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	144912-63-0
PubChem CID	6918236
ChemSpider	5293443
UNII	FX5AUU7Z8T
KEGG	D05447
CompTox Dashboard (EPA)	DTXSID70162846
ECHA InfoCard	100.222.780
Chemical and physical data
Formula	C9H13N2O5P
Molar mass	260.184 g/mol g·mol
3D model (JSmol)	Interactive image
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.

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