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GYKI 52466

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GYKI 52466
Skeletal formula
Space-filling model of GYKI-52,466
Names
Preferred IUPAC name 4-(8-Methyl-2H,9H-dioxolobenzodiazepin-5-yl)aniline
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.162.378 Edit this at Wikidata
IUPHAR/BPS
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3Key: LFBZZHVSGAHQPP-UHFFFAOYSA-N
  • InChI=1/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3Key: LFBZZHVSGAHQPP-UHFFFAOYAH
SMILES
  • CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
Properties
Chemical formula C17H15N3O2
Molar mass 293.326 g·mol
Appearance Yellow solid (HCl salt)
Density 1.393 g/cm
Solubility in water >10 mg/mL (HCl salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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 (1998). "Allosteric regulation of α-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 (3): 615–629. doi:10.1016/s0306-4522(98)00109-2. PMID 9758228. S2CID 14817743.
  2. Donevan, Sean D.; Rogawski, Michael A. (1993). "GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/Kainate receptor responses". Neuron. 10 (1): 51–59. doi:10.1016/0896-6273(93)90241-i. PMID 7678966. S2CID 16011527.
  3. Tarnawa, István; Farkas, Sándor; Berzsenyi, Pál; Pataki, Ágnes; Andrási, Ferenc (1989). "Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466". European Journal of Pharmacology. 167 (2): 193–199. doi:10.1016/0014-2999(89)90579-7. PMID 2574112.
  4. Rzeski, W.; Turski, L.; Ikonomidou, C. (2001). "Glutamate antagonists limit tumor growth". Proceedings of the National Academy of Sciences. 98 (11): 6372–6377. doi:10.1073/pnas.091113598. PMC 33475. PMID 11331750.
  5. Paternain, Ana V.; Morales, Miguel; Lerma, Juan (1995). "Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons". Neuron. 14 (1): 185–189. doi:10.1016/0896-6273(95)90253-8. PMID 7826635. S2CID 6037517.
  6. Szabados, Tamás; Gigler, Gábor; Gacsályi, István; Gyertyán, István; Lévay, György (2001). "Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655". Brain Research Bulletin. 55 (3): 387–391. doi:10.1016/s0361-9230(01)00516-0. PMID 11489346. S2CID 23142293.
Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Benzodiazepines
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Thienotriazolodiazepines
Thienobenzodiazepines*
Pyridodiazepines
Pyridotriazolodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Pyrrolobenzodiazepines*
Benzodiazepine prodrugs
* atypical activity profile (not GABAA receptor ligands)
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