6-Nitro-7-sulfamoylbenzo[f]quinoxaline-2,3-Dione

• CAT Number: R000332
• CAS Number: 118876-58-7
• Molecular Formula: C12H8N4O6S
• Molecular Weight: 336.278
• Purity: ≥95%
• Synonyms: 1,2,3,4-Tetrahydro-6-nitro-2,3-dioxo-benzo[f]quinoxaline-7-sulfonamide; NBQX
• Target: Neuronal Signaling
• Solubility: Soluble in DMSO > 10 mM
• Storage: Store at RT
• IUPAC Name: 6-nitro-2,3-dioxo-1,4-dihydrobenzo[f]quinoxaline-7-sulfonamide
• InChI: InChI=1S/C12H8N4O6S/c13-23(21,22)8-3-1-2-5-9(8)7(16(19)20)4-6-10(5)15-12(18)11(17)14-6/h1-4H,(H,14,17)(H,15,18)(H2,13,21,22)
• InChIKey: UQNAFPHGVPVTAL-UHFFFAOYSA-N
• SMILES: C1=CC2=C3C(=CC(=C2C(=C1)S(=O)(=O)N)[N+](=O)[O-])NC(=O)C(=O)N3

NBQX is an AMPA receptor antagonist. NBQX blocks AMPA receptors in micromolar concentrations (~10–20 µM) and also blocks kainate receptors. In experiments, it is used to counter glutamate excitotoxicity. NBQX was found to have anticonvulsant activity in rodent seizure models. As the disodium salt, NBQX is soluble in water at high concentrations (at least up to 100 mM).

Reference

1: Twele F, Bankstahl M, Klein S, Römermann K, Löscher W. The AMPA receptor antagonist NBQX exerts anti-seizure but not antiepileptogenic effects in the intrahippocampal kainate mouse model of mesial temporal lobe epilepsy. Neuropharmacology. 2015 Aug;95:234-42. doi: 10.1016/j.neuropharm.2015.03.014. Epub 2015 Mar 31. PubMed PMID: 25839899.2: Lippman-Bell JJ, Rakhade SN, Klein PM, Obeid M, Jackson MC, Joseph A, Jensen FE. AMPA receptor antagonist NBQX attenuates later-life epileptic seizures and autistic-like social deficits following neonatal seizures. Epilepsia. 2013 Nov;54(11):1922-32. doi: 10.1111/epi.12378. Epub 2013 Oct 1. PubMed PMID: 24117347; PubMed Central PMCID: PMC4262152.3: Potschka H, Pekcec A, Weinhold B, Gerardy-Schahn R. Deficiency of neural cell adhesion molecule or its polysialylation modulates pharmacological effects of the AMPA receptor antagonist NBQX. Neuroscience. 2008 Apr 9;152(4):1093-8. doi: 10.1016/j.neuroscience.2007.09.027. Epub 2007 Sep 20. PubMed PMID: 18329813.4: Zbarska S, Bloedel JR, Bracha V. Cerebellar dysfunction explains the extinction-like abolition of conditioned eyeblinks after NBQX injections in the inferior olive. J Neurosci. 2008 Jan 2;28(1):10-20. doi: 10.1523/JNEUROSCI.3403-07.2008. PubMed PMID: 18171918.5: Lojková D, Zivanović D, Mares P. Different effects of nonNMDA and NMDA receptor antagonists (NBQX and dizocilpine) on cortical epileptic afterdischarges in rats. Brain Res. 2006 Dec 8;1124(1):167-75. Epub 2006 Oct 27. PubMed PMID: 17070784.6: Kong LL, Yu LC. It is AMPA receptor, not kainate receptor, that contributes to the NBQX-induced antinociception in the spinal cord of rats. Brain Res. 2006 Jul 19;1100(1):73-7. Epub 2006 Jun 13. PubMed PMID: 16777075.7: Yoon MH, Bae HB, Choi JI, Jeong SW, Chung SS, Yoo KY, Jeong CY, Kim SJ, Chung ST, Kim CM, An TH. Evaluation of interaction between intrathecal adenosine and MK801 or NBQX in a rat formalin pain model. Pharmacology. 2005 Nov;75(3):157-64. Epub 2005 Sep 15. PubMed PMID: 16166819.8: Yoon MH, Bae HB, Choi JI. Antinociceptive interactions between intrathecal gabapentin and MK801 or NBQX in rat formalin test. J Korean Med Sci. 2005 Apr;20(2):307-12. PubMed PMID: 15832006; PubMed Central PMCID: PMC2808611.9: Zahn PK, Pogatzki-Zahn EM, Brennan TJ. Spinal administration of MK-801 and NBQX demonstrates NMDA-independent dorsal horn sensitization in incisional pain. Pain. 2005 Apr;114(3):499-510. PubMed PMID: 15777875.10: Koh S, Tibayan FD, Simpson JN, Jensen FE. NBQX or topiramate treatment after perinatal hypoxia-induced seizures prevents later increases in seizure-induced neuronal injury. Epilepsia. 2004 Jun;45(6):569-75. PubMed PMID: 15144420.11: Van Damme P, Leyssen M, Callewaert G, Robberecht W, Van Den Bosch L. The AMPA receptor antagonist NBQX prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis. Neurosci Lett. 2003 Jun 5;343(2):81-4. PubMed PMID: 12759169.12: Goda M, Isono M, Fujiki M, Kobayashi H. Both MK801 and NBQX reduce the neuronal damage after impact-acceleration brain injury. J Neurotrauma. 2002 Nov;19(11):1445-56. PubMed PMID: 12490009.13: Mu X, Azbill RD, Springer JE. NBQX treatment improves mitochondrial function and reduces oxidative events after spinal cord injury. J Neurotrauma. 2002 Aug;19(8):917-27. PubMed PMID: 12225652.14: Pitsikas N, Rigamonti AE, Cella SG, Muller EE. The non-NMDA receptor antagonist NBQX does not affect rats performance in the object recognition task. Pharmacol Res. 2002 Jan;45(1):43-6. PubMed PMID: 11820860.15: Jakobsen B, Zimmer J. Chronic exposure of kainate and NBQX changes AMPA toxicity in hippocampal slice cultures. Neuroreport. 2001 Nov 16;12(16):3593-7. PubMed PMID: 11733718.16: Zheng H, Patterson C, Berthoud HR. Behavioral analysis of anorexia produced by hindbrain injections of AMPA receptor antagonist NBQX in rats. Am J Physiol Regul Integr Comp Physiol. 2002 Jan;282(1):R147-55. PubMed PMID: 11742833.17: Emch GS, Hermann GE, Rogers RC. TNF-alpha-induced c-Fos generation in the nucleus of the solitary tract is blocked by NBQX and MK-801. Am J Physiol Regul Integr Comp Physiol. 2001 Nov;281(5):R1394-400. PubMed PMID: 11641108.18: Pitsikas N, Brambilla A, Besozzi C, Bonali P, Fodritto F, Grippa N, Scandroglio A, Borsini F. Effects of cerestat and NBQX on functional and morphological outcomes in rat focal cerebral ischemia. Pharmacol Biochem Behav. 2001 Mar;68(3):443-7. PubMed PMID: 11325397.19: Kapus G, Székely JI, Durand J, Ruiz A, Tarnawa I. AMPA receptor antagonists, GYKI 52466 and NBQX, do not block the induction of long-term potentiation at therapeutically relevant concentrations. Brain Res Bull. 2000 Aug;52(6):511-7. PubMed PMID: 10974490.20: Görgülü A, Kiriş T, Unal F, Turkoğlu U, Küçük M, Cobanoğlu S. Superoxide dismutase activity and the effects of NBQX and CPP on lipid peroxidation in experimental spinal cord injury. Res Exp Med (Berl). 2000 Apr;199(5):285-93. PubMed PMID: 10815757.