Fanapanel

Fanapanel (INN, code name ZK-200775), also known as MPQX, is a quinoxalinedione derivative drug which acts as a competitive antagonist of the AMPA receptor.[1] It was under development by Schering AG for the treatment of cerebral ischemia associated with stroke and trauma, but clinical trials were halted for safety reasons related to possible glial cell toxicity and due to intolerable side effects such as excessive sedation, reduction in consciousness (consisting of stupor and coma), and transient neurological deterioration.[2][3] The drug was also observed to produce visual alteration and impairment, including blurred vision, strongly impaired color perception, and reduced visual acuity and dark vision, side effects thought to be caused by blockade of AMPA receptors in the retina.[4]

Fanapanel
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • {[7-(4-Morpholinyl)-2,3-dioxo-6-(trifluoromethyl)-3,4-dihydro-1(2H)-quinoxalinyl]methyl}phosphonic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H15F3N3O6P
Molar mass409.258 g·mol−1
3D model (JSmol)
SMILES
  • c1c(c(cc2c1[nH]c(=O)c(=O)n2CP(=O)(O)O)N3CCOCC3)C(F)(F)F
InChI
  • InChI=1S/C14H15F3N3O6P/c15-14(16,17)8-5-9-11(6-10(8)19-1-3-26-4-2-19)20(7-27(23,24)25)13(22)12(21)18-9/h5-6H,1-4,7H2,(H,18,21)(H2,23,24,25)
  • Key:WZMQMKNCWDCCMT-UHFFFAOYSA-N

References
  1. Turski L, Huth A, Sheardown M, et al. (September 1998). "ZK200775: a phosphonate quinoxalinedione AMPA antagonist for neuroprotection in stroke and trauma". Proc. Natl. Acad. Sci. U.S.A. 95 (18): 10960–5. Bibcode:1998PNAS...9510960T. doi:10.1073/pnas.95.18.10960. PMC 28003. PMID 9724812.
  2. Walters MR, Kaste M, Lees KR, et al. (2005). "The AMPA antagonist ZK 200775 in patients with acute ischaemic stroke: a double-blind, multicentre, placebo-controlled safety and tolerability study". Cerebrovasc. Dis. 20 (5): 304–9. doi:10.1159/000087929. PMID 16131799. S2CID 25034903.
  3. Elting JW, Sulter GA, Kaste M, et al. (December 2002). "AMPA antagonist ZK200775 in patients with acute ischemic stroke: possible glial cell toxicity detected by monitoring of S-100B serum levels". Stroke. 33 (12): 2813–8. doi:10.1161/01.str.0000043823.37955.fb. PMID 12468775.
  4. Gwinn, Katrina; Bergholz, Richard; Staks, Thomas; Rüther, Klaus (2010). "Effects of the AMPA Antagonist ZK 200775 on Visual Function: A Randomized Controlled Trial". PLOS ONE. 5 (8): e12111. Bibcode:2010PLoSO...512111B. doi:10.1371/journal.pone.0012111. ISSN 1932-6203. PMC 2920815. PMID 20711429.


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