perzinfotel

{{Short description|Chemical compound}}

{{Drugbox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 443223642

|IUPAC_name = 2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethylphosphonic acid

|image = Perzinfotel.svg

|width = 150

|CAS_number_Ref = {{cascite|correct|??}}

|CAS_number = 144912-63-0

|ATC_prefix = none

|PubChem = 6918236

|DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = FX5AUU7Z8T

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = D05447

|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

|ChemSpiderID = 5293443

|C=9 | H=13 | N=2 | O=5 | P=1

|smiles = C1CNC2=C(C(=O)C2=O)N(C1)CCP(=O)(O)O

|StdInChI_Ref = {{stdinchicite|changed|chemspider}}

|StdInChI = 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)

|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

|StdInChIKey = BDABGOLMYNHHTR-UHFFFAOYSA-N

}}

Perzinfotel (EAA-090) is a drug which acts as a potent NMDA antagonist.{{cite journal | vauthors = Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, Miller TL, Tasse RP, Zaleska MM, Moyer JA | display-authors = 6 | title = 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 = Journal of Medicinal Chemistry | volume = 41 | issue = 2 | pages = 236–46 | date = January 1998 | pmid = 9457246 | doi = 10.1021/jm970504g }} It has neuroprotective effects and has been investigated for the treatment of stroke,{{cite journal | vauthors = Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S | title = 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 = The Journal of Pharmacology and Experimental Therapeutics | volume = 310 | issue = 2 | pages = 563–70 | date = August 2004 | pmid = 15075380 | doi = 10.1124/jpet.104.066092 | s2cid = 25505657 }} but lacks analgesic effects.{{cite journal | vauthors = Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S | title = 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 = The Journal of Pharmacology and Experimental Therapeutics | volume = 313 | issue = 3 | pages = 1379–86 | date = June 2005 | pmid = 15764736 | doi = 10.1124/jpet.105.084467 | s2cid = 12989500}} Nevertheless, it shows a good safety profile compared to older drugs, although further development of this drug has been discontinued.{{cite web | title = Perzinfotel | url = http://adisinsight.springer.com/drugs/800009946 | work = Adis International Ltd. | publisher = Springer Nature Switzerland AG }}

Prodrugs were developed since the oral bioavailability of perzinfotel is only around 3-5%.{{cite journal | vauthors = Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, Magolda R, Sze JY, Brandt MR, Cummons TA, Kowal D, Pangalos MN, Zupan B, Hoffmann M, May M, Mugford C, Kennedy J, Childers WE | display-authors = 6 | title = Prodrugs of perzinfotel with improved oral bioavailability | journal = Journal of Medicinal Chemistry | volume = 52 | issue = 3 | pages = 771–8 | date = February 2009 | pmid = 19146418 | doi = 10.1021/jm8011799 }}