Perzinfotel

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]

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^Y
PubChem CID	6918236
ChemSpider	5293443^N
UNII	FX5AUU7Z8T
KEGG	D05447^Y
CompTox Dashboard (EPA)	DTXSID70162846
ECHA InfoCard	100.222.780
Chemical and physical data
Formula	C9H13N2O5P
Molar mass	260.186 g·mol^−1
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)^N Key:BDABGOLMYNHHTR-UHFFFAOYSA-N^N
^NY (what is this?)  (verify)

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, et al. (January 1998). "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. 41 (2): 236–46. doi:10.1021/jm970504g. PMID 9457246.
2. Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, et al. (August 2004). "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)". The 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 [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". The Journal of Pharmacology and Experimental Therapeutics. 313 (3): 1379–86. doi:10.1124/jpet.105.084467. PMID 15764736.
4. "Perzinfotel". Adis International Ltd. Springer Nature Switzerland AG.
5. Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, et al. (February 2009). "Prodrugs of perzinfotel with improved oral bioavailability". Journal of Medicinal Chemistry. 52 (3): 771–8. doi:10.1021/jm8011799. PMID 19146418.