GYKI-52,466
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GYKI-52,466
GYKI-52,466
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IUPAC name 4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline | |
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3D model (JSmol) |
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ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.162.378 [25] |
IUPHAR/BPS |
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KEGG |
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CompTox Dashboard(EPA) |
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InChI
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Properties | |
C17H15N3O2 | |
Molar mass | 293.32 g/mol |
Appearance | Yellow solid (HCl salt) |
Density | 1.393 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 isYN ?) | |
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.
Names | |
---|---|
IUPAC name 4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline | |
Identifiers | |
CAS Number | |
3D model (JSmol) |
|
ChEBI |
|
ChEMBL |
|
ChemSpider |
|
ECHA InfoCard | 100.162.378 [25] |
IUPHAR/BPS |
|
KEGG |
|
PubChemCID |
|
UNII |
|
CompTox Dashboard(EPA) |
|
InChI
| |
SMILES
| |
Properties | |
C17H15N3O2 | |
Molar mass | 293.32 g/mol |
Appearance | Yellow solid (HCl salt) |
Density | 1.393 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 isYN ?) | |
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