NBQX

Structural formula
General
Surname	NBQX
other names	2,3-Dioxo-6-nitro-1,2,3,4-tetrahydrobenzo [ f ] quinoxaline-7-sulfonamide
Molecular formula	C 15 H 16 O 6 • C 15 H 18 O 7
Brief description	brown to very dark red-brown powder
External identifiers / databases
EC number	621-100-6
ECHA InfoCard	100.149.984
PubChem	3272524
ChemSpider	2521927
Wikidata	Q972076
properties
Molar mass	336.281 g · mol -1
Physical state	firmly
solubility	soluble to 100 mM in DMSO; as the disodium salt at 100 mM in water;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

NBQX (2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo [ f ] quinoxaline-2,3-dione) is a potent, selective and competitive AMPA - antagonist developed by the Danish pharmaceutical company Ferrosan 1990th

A sample from NBQX.

NBQX blocks AMPA and kainate receptors in a concentration of typically 10–20 µM. It is used to counteract glutamate and to block AMPA synaptic connections. NBQX has neuroprotective and anticonvulsant effects in the rodent model and has potential applications against multiple sclerosis . As a disodium salt, NBQX is very soluble in water.

In high doses of 60 mg / kg body weight in a rodent model, NBQX can trigger ataxias , similar to those that occur during acute alcohol intoxication . It also causes kidney damage. Even at lower doses of 30 mg / kg, NBQX interferes with the learning process and the motor system. These effects, along with difficulties in transporting NBQX as an active ingredient into the nervous system, make it unattractive as a pharmaceutical.

Individual evidence

↑ ^a ^b ^c ^d data sheet NBQX from Sigma-Aldrich , accessed on May 26, 2014 ( PDF ).
↑ Abcam: NBQX | AMPA and Kainate antagonist , accessed August 9, 2014
↑ ^a ^b NBQX data sheet at Tocris, accessed on May 26, 2014
↑ Data sheet NBQX from Merck, accessed on May 26, 2014
^ MJ Sheardown: The pharmacology of AMPA receptors and their antagonists. In: Stroke . Volume 24, Number 12 Suppl, December 1993, pp. I146-1147, ISSN 0039-2499 . PMID 7504337 .
↑ MJ Sheardown, EO Nielsen, AJ Hansen, P. Jacobsen, T. Honoré: 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo (F) quinoxaline: a neuroprotectant for cerebral ischemia. In: Science Volume 247, Number 4942, February 1990, pp. 571-574, ISSN 0036-8075 . PMID 2154034 .
↑ R. Gill, L. Nordholm, D. Lodge: The neuroprotective actions of 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo (F) quinoxaline (NBQX) in a rat focal ischaemia model. In: Brain research. Volume 580, Number 1-2, May 1992, pp. 35-43, ISSN 0006-8993 . PMID 1504814 .
^ GJ Lees, W. Leong: Differential effects of NBQX on the distal and local toxicity of glutamate agonists administered intra-hippocampally. In: Brain research. Volume 628, Number 1-2, November 1993, pp 1-7, ISSN 0006-8993 . PMID 7508807 .
↑ S. Yamaguchi, SD Donevan, MA Rogawski: anticonvulsant activity of AMPA / kainate antagonists: comparison of GYKI 52466 and NBOX in maximum electroshock and chemoconvulsant seizure models. In: Epilepsy research. Volume 15, Number 3, July 1993, pp. 179-184, ISSN 0920-1211 . PMID 7693450 .
↑ D. Pitt, P. Werner, CS Raine: Glutamate excitotoxicity in a model of multiple sclerosis. In: Nature Medicine . Volume 6, Number 1, January 2000, pp. 67-70, ISSN 1078-8956 . doi : 10.1038 / 71555 . PMID 10613826 .
^ ^A ^b Paul L. Herrling: Excitatory Amino Acids. Academic Press, 1997, ISBN 978-0-080-53134-2 , p. 89 ( limited preview in Google book search).
↑ P. Filliata, I. Pernot Marinoa, D. Baubichona, G. Lallementa: Behavioral Effects of NBQX, a competitive antagonist of the AMPA Receptors. In: Pharmacology, Biochemistry and Behavior . Volume 59, Number 4, April 1998, pp. 1087-92. doi : 10.1016 / S0091-3057 (97) 00518-2 . PMID 9586871 .

[Sigma-1] ta sheet NBQX from Sigma-Aldrich , accessed on May 26, 2014 ( PDF ).

[Abcam-2] Abcam: NBQX | AMPA and Kainate antagonist , accessed August 9, 2014

[tocris-3] NBQX data sheet at Tocris, accessed on May 26, 2014

[Merck-4] Data sheet NBQX from Merck, accessed on May 26, 2014

[5] MJ Sheardown: The pharmacology of AMPA receptors and their antagonists. In: Stroke . Volume 24, Number 12 Suppl, December 1993, pp. I146-1147, ISSN 0039-2499 . PMID 7504337 .

[6] MJ Sheardown, EO Nielsen, AJ Hansen, P. Jacobsen, T. Honoré: 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo (F) quinoxaline: a neuroprotectant for cerebral ischemia. In: Science Volume 247, Number 4942, February 1990, pp. 571-574, ISSN 0036-8075 . PMID 2154034 .

[7] R. Gill, L. Nordholm, D. Lodge: The neuroprotective actions of 2,3-dihydroxy-6-nitro-7-sulfamoyl-benzo (F) quinoxaline (NBQX) in a rat focal ischaemia model. In: Brain research. Volume 580, Number 1-2, May 1992, pp. 35-43, ISSN 0006-8993 . PMID 1504814 .

[8] GJ Lees, W. Leong: Differential effects of NBQX on the distal and local toxicity of glutamate agonists administered intra-hippocampally. In: Brain research. Volume 628, Number 1-2, November 1993, pp 1-7, ISSN 0006-8993 . PMID 7508807 .

[9] S. Yamaguchi, SD Donevan, MA Rogawski: anticonvulsant activity of AMPA / kainate antagonists: comparison of GYKI 52466 and NBOX in maximum electroshock and chemoconvulsant seizure models. In: Epilepsy research. Volume 15, Number 3, July 1993, pp. 179-184, ISSN 0920-1211 . PMID 7693450 .

[10] D. Pitt, P. Werner, CS Raine: Glutamate excitotoxicity in a model of multiple sclerosis. In: Nature Medicine . Volume 6, Number 1, January 2000, pp. 67-70, ISSN 1078-8956 . doi : 10.1038 / 71555 . PMID 10613826 .

[Herrling1997-11] A ^b Paul L. Herrling: Excitatory Amino Acids. Academic Press, 1997, ISBN 978-0-080-53134-2 , p. 89 ( limited preview in Google book search).

[12] P. Filliata, I. Pernot Marinoa, D. Baubichona, G. Lallementa: Behavioral Effects of NBQX, a competitive antagonist of the AMPA Receptors. In: Pharmacology, Biochemistry and Behavior . Volume 59, Number 4, April 1998, pp. 1087-92. doi : 10.1016 / S0091-3057 (97) 00518-2 . PMID 9586871 .