GYKI-52,466

GYKI-52,466[1][2][3][4][5][6][7]
Names
IUPAC name
4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.378
KEGG
UNII
Properties
C17H15N3O2
Molar mass 293.32 g/mol
Appearance Yellow solid (HCl salt)
Density 1.393 g/cm3
>10 mg/mL (HCl salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

GYKI-52466 is a 2,3-benzodiazepine that acts as an ionotropic glutamate receptor antagonist, which is a non-competitive AMPA receptor antagonist (IC50 values are 10-20, ~ 450 and >> 50 μM for AMPA- , kainate- and NMDA-induced responses respectively), orally-active anticonvulsant, and skeletal muscle relaxant. Unlike conventional 1,4-benzodiazepines, GYKI-52466 and related 2,3-benzodiazepines do not act on GABAA receptors. Like other AMPA receptor antagonists, GYKI-52466 has anticonvulsant and neuroprotective properties.

See also

References

  1. Donevan, S.D., Rogawski, M.A., Allosteric regulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionate receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines. Neuroscience 87, 615, (1998)
  2. Donevan, S.D., Rogawski, M.A., GYKI 52466, a 2,3-benzodiazepine is a highly selective, non-competitive antagonist of AMPA/kainate receptor responses. Neuron 10, 51, (1993)
  3. Wilding, T.J., Huettner, J.E., Differential antagonism of alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid-preferring and kainate-preferring receptors by 2,3-benzodiazepines. Mol. Pharmacol. 47, 582, (1995)
  4. Tarnawa et al. (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur. J.Pharmacol. 167 193
  5. Paternain et al. (1995) Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons. Neuron 14 185.
  6. Rzeski et al. (2001) Glutamate antagonists limit tumor growth. Proc. Natl.Acad. Sci.USA 98 6372.
  7. Szabados et al. (2001) Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain Res. Bull. 55 387.
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