ペルジンホテル

ペルジンホテル
臨床データ
ATCコード	none;
識別子
	IUPAC名 2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethylphosphonic acid;
CAS登録番号	144912-63-0 ;
PubChem; CID	6918236;
ChemSpider	5293443 ;
UNII	FX5AUU7Z8T;
KEGG	D05447 ;
CompTox; Dashboard; (EPA)	DTXSID70162846 ;
ECHA InfoCard	100.222.780
化学的および物理的データ
化学式	C9H13N2O5P
分子量	260.184 g/mol 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) ; Key:BDABGOLMYNHHTR-UHFFFAOYSA-N ;
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ペルジンホテル(Perzinfotel)またはEAA-090は、強力なNMDAのアンタゴニストとして作用する薬剤である^[1]。神経防護効果を持ち、脳梗塞の治療用に研究されているが^[2]、鎮痛剤効果は持たない^[3]。他の薬剤と比べて安全性が高いが、研究はなお続いている。

合成

↑ 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
↑ 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
↑ 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