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Chemical compound
Fanapanel
ATC code
{[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 )
Formula C 14 H 15 F 3 N 3 O 6 P
Molar mass 409.258 g·mol−1 3D model (
JSmol )
c1c(c(cc2c1[nH]c(=O)c(=O)n2CP(=O)(O)O)N3CCOCC3)C(F)(F)F
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
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]
References
^ Turski L, Huth A, Sheardown M, McDonald F, Neuhaus R, Schneider HH, et al. (September 1998).
"ZK200775: a phosphonate quinoxalinedione AMPA antagonist for neuroprotection in stroke and trauma" . Proceedings of the National Academy of Sciences of the United States of America . 95 (18): 10960–10965.
Bibcode :
1998PNAS...9510960T .
doi :
10.1073/pnas.95.18.10960 .
PMC
28003 .
PMID
9724812 .
^ Walters MR, Kaste M, Lees KR, Diener HC, Hommel M, De Keyser J, et al. (2005). "The AMPA antagonist ZK 200775 in patients with acute ischaemic stroke: a double-blind, multicentre, placebo-controlled safety and tolerability study". Cerebrovascular Diseases . 20 (5): 304–309.
doi :
10.1159/000087929 .
PMID
16131799 .
S2CID
25034903 .
^ Elting JW, Sulter GA, Kaste M, Lees KR, Diener HC, Hommel 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): 2813–2818.
doi :
10.1161/01.str.0000043823.37955.fb .
PMID
12468775 .
^ Bergholz R, Staks T, Rüther K (August 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 .
PMC
2920815 .
PMID
20711429 .
AMPAR Tooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KAR Tooltip Kainate receptor
NMDAR Tooltip N-Methyl-D-aspartate receptor