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GYKI-52,466

GYKI-52,466

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.

GYKI-52,466[[CITE|1|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20Allosteric%20regulati]][[CITE|2|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20GYKI%2052466%2C%20a%202%2C3-b]][[CITE|3|https://openlibrary.org/search?q=Wilding%2C%20T.J.%2C%20Huettner%2C%20J.E.%2C%20Differential%20antago]][[CITE|4|https://openlibrary.org/search?q=Tarnawa%20et%20al.%20%281989%29%20Electrophysiological%20studies]][[CITE|5|https://openlibrary.org/search?q=Paternain%20et%20al.%20%281995%29%20Selective%20antagonism%20of%20AM]][[CITE|6|https://openlibrary.org/search?q=Rzeski%20et%20al.%20%282001%29%20Glutamate%20antagonists%20limit%20t]][[CITE|7|https://openlibrary.org/search?q=Szabados%20et%20al.%20%282001%29%20Comparison%20of%20anticonvulsiv]]
Space-filling model of GYKI-52,466
Names
IUPAC name
4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
CAS Number
  • 102771-26-6 [19]☑Y
  • 192065-56-8 [20](HCl salt)☒N
3D model (JSmol)
  • Interactive image [21]
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.162.378 [25]
IUPHAR/BPS
KEGG
PubChemCID
UNII
CompTox Dashboard(EPA)
Properties
C17H15N3O2
Molar mass293.32 g/mol
AppearanceYellow solid (HCl salt)
Density1.393 g/cm3
Solubility in water
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).
☒Nverify [31] (what is☑Y☒N ?)
Infobox references

See also

  • GYKI-52895, another 2,3-benzodiazepine with other than GABAergic function

  • Tifluadom

  • Lufuradom

References

[1]
Citation Linkopenlibrary.orgDonevan, 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)
Sep 30, 2019, 5:10 AM
[2]
Citation Linkopenlibrary.orgDonevan, 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)
Sep 30, 2019, 5:10 AM
[3]
Citation Linkopenlibrary.orgWilding, 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)
Sep 30, 2019, 5:10 AM
[4]
Citation Linkopenlibrary.orgTarnawa et al. (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur. J.Pharmacol. 167 193
Sep 30, 2019, 5:10 AM
[5]
Citation Linkopenlibrary.orgPaternain et al. (1995) Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons. Neuron 14 185.
Sep 30, 2019, 5:10 AM
[6]
Citation Linkopenlibrary.orgRzeski et al. (2001) Glutamate antagonists limit tumor growth. Proc. Natl.Acad. Sci.USA 98 6372.
Sep 30, 2019, 5:10 AM
[7]
Citation Linkopenlibrary.orgSzabados 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.
Sep 30, 2019, 5:10 AM
[8]
Citation Linkwww.commonchemistry.org102771-26-6
Sep 30, 2019, 5:10 AM
[9]
Citation Linkwww.commonchemistry.org192065-56-8
Sep 30, 2019, 5:10 AM
[10]
Citation Linkchemapps.stolaf.eduInteractive image
Sep 30, 2019, 5:10 AM
[11]
Citation Linkwww.ebi.ac.ukCHEBI:79560
Sep 30, 2019, 5:10 AM
[12]
Citation Linkwww.ebi.ac.ukChEMBL275006
Sep 30, 2019, 5:10 AM
[13]
Citation Linkwww.chemspider.com3417
Sep 30, 2019, 5:10 AM
[14]
Citation Linkwww.guidetopharmacology.org4210
Sep 30, 2019, 5:10 AM
[15]
Citation Linkwww.kegg.jpC15040
Sep 30, 2019, 5:10 AM
[16]
Citation Linkpubchem.ncbi.nlm.nih.gov3538
Sep 30, 2019, 5:10 AM
[17]
Citation Linkfdasis.nlm.nih.gov471V8NZ5X3
Sep 30, 2019, 5:10 AM
[18]
Citation Linkcomptox.epa.govDTXSID40145500
Sep 30, 2019, 5:10 AM
[19]
Citation Linkwww.commonchemistry.org102771-26-6
Sep 30, 2019, 5:10 AM
[20]
Citation Linkwww.commonchemistry.org192065-56-8
Sep 30, 2019, 5:10 AM