Perzinfotel

Perzinfotel

Clinical data
ATC code	none
Identifiers
IUPAC name 2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethylphosphonic acid
CAS Number	144912-63-0
PubChem (CID)	6918236
ChemSpider	5293443
UNII	FX5AUU7Z8T
KEGG	D05447
ECHA InfoCard	100.222.780
Chemical and physical data
Formula	C9H13N2O5P
Molar mass	260.184 g/mol
3D model (Jmol)	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
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Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist.^[1] It has neuroprotective effects and has been investigated for the treatment of stroke,^[2] but lacks analgesic effects.^[3] Nevertheless, it shows a good safety profile compared to older drugs, although further development of this drug has been discontinued.^[4]

Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.^[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 [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]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-[8,9-dioxo-2,6-diazabicyclo [5.2.0]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 [EAA-090; [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]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.