Zonampanel

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 328036

CAS#: 210245-80-0

Description: Zonampanel, also known as YM-872, is an AMPA receptor antagonist potentially for the treatment of stroke. YM872, attenuates regional cerebral edema and IgG immunoreactivity following experimental brain injury in rats. YM872, attenuates cortical tissue loss, regional cerebral edema, and neurological motor deficits after experimental brain injury in rats.


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Zonampanel is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 328036
Name: Zonampanel
CAS#: 210245-80-0
Chemical Formula: C13H9N5O6
Exact Mass: 331.0553
Molecular Weight: 331.244
Elemental Analysis: C, 47.14; H, 2.74; N, 21.14; O, 28.98


Synonym: Zonampanel; YM-872; YM872; YM 872.

IUPAC/Chemical Name: 7-(1H-Imidazol-1-yl)-6-nitro-2,3-dioxo-3,4-dihydro-1(2H)-quinoxalineacetic acid

InChi Key: SPXYHZRWPRQLNS-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H9N5O6/c19-11(20)5-17-8-4-9(16-2-1-14-6-16)10(18(23)24)3-7(8)15-12(21)13(17)22/h1-4,6H,5H2,(H,15,21)(H,19,20)

SMILES Code: O=C(O)CN1C(C(NC2=C1C=C(N3C=CN=C3)C([N+]([O-])=O)=C2)=O)=O


Technical Data

Appearance:
White to off-white solid powder.

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

210245-80-0 (Zonampanel anhydrouse)
466685-98-3 (Zonampanel monohydrous)


References

1: O'Hare Doig RL, Bartlett CA, Smith NM, Hodgetts SI, Dunlop SA, Hool L, Fitzgerald M. Specific combinations of Ca(2+) channel inhibitors reduce excessive Ca(2+) influx as a consequence of oxidative stress and increase neuronal and glial cell viability in vitro. Neuroscience. 2016 Oct 8. pii: S0306-4522(16)30514-0. doi: 10.1016/j.neuroscience.2016.10.005. PubMed PMID: 27725216.

2: Watanabe T, Ohtani T, Aihara M, Ishiuchi S. Enhanced antitumor effect of YM872 and AG1296 combination treatment on human glioblastoma xenograft models. J Neurosurg. 2013 Apr;118(4):838-45. doi: 10.3171/2012.11.JNS12362. PubMed PMID: 23311938.

3: Retraction: Interaction between a NMDA receptor antagonist, AP-5 and an AMPA receptor antagonist, YM 872 in antinociception in the spinal cord by Nishiyama T. Acta Anaesthesiol Scand. 2009 Feb;53(2):268. doi: 10.1111/j.1399-6576.2009.01903.x. PubMed PMID: 19175582.

4: Minematsu T, Hashimoto T, Usui T, Kamimura H. Characterization of renal tubular apical efflux of zonampanel, an alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor antagonist, in humans. Xenobiotica. 2008 Sep;38(9):1191-202. doi: 10.1080/00498250802187286 . PubMed PMID: 18609448.

5: Minematsu T, Hashimoto T, Aoki T, Usui T, Kamimura H. Role of organic anion transporters in the pharmacokinetics of zonampanel, an alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor antagonist, in rats. Drug Metab Dispos. 2008 Aug;36(8):1496-504. doi: 10.1124/dmd.107.019828. PubMed PMID: 18443035.

6: Nishiyama T. Interaction between a NMDA receptor antagonist, AP-5 and an AMPA receptor antagonist, YM 872 in antinociception in the spinal cord. Acta Anaesthesiol Scand. 2008 Apr;52(4):493-8. doi: 10.1111/j.1399-6576.2008.01593.x. Retraction in: Acta Anaesthesiol Scand. 2009 Feb;53(2):268. PubMed PMID: 18339155.

7: King TE, Barr GA. Spinal cord ionotropic glutamate receptors function in formalin-induced nociception in preweaning rats. Psychopharmacology (Berl). 2007 Jul;192(4):489-98. PubMed PMID: 17356878.

8: Koizumi Y, Matsumoto M, Yamashita A, Tsuruta S, Ohtake T, Sakabe T. The effects of an AMPA receptor antagonist on the neurotoxicity of tetracaine intrathecally administered in rabbits. Anesth Analg. 2006 Mar;102(3):930-6. PubMed PMID: 16492854.

9: Hara H, Yamada N, Kodama M, Matsumoto Y, Wake Y, Kuroda S. Effect of YM872, a selective and highly water-soluble AMPA receptor antagonist, in the rat kindling and rekindling model of epilepsy. Eur J Pharmacol. 2006 Feb 15;531(1-3):59-65. PubMed PMID: 16403498.

10: Minematsu T, Sohda KY, Hashimoto T, Imai H, Usui T, Kamimura H. Identification of metabolites of [14C]zonampanel, an a-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor antagonist, following intravenous infusion in healthy volunteers. Xenobiotica. 2005 Apr;35(4):359-71. PubMed PMID: 16019957.

11: Sohda KY, Minematsu T, Hashimoto T, Suzumura K, Funatsu M, Suzuki K, Imai H, Usui T, Kamimura H. Application of LC-NMR for characterization of rat urinary metabolites of zonampanel monohydrate (YM872). Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1322-5. PubMed PMID: 15516754.

12: Hashimoto T, Narikawa S, Huang XL, Minematsu T, Usui T, Kamimura H, Endou H. Characterization of the renal tubular transport of zonampanel, a novel alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor antagonist, by human organic anion transporters. Drug Metab Dispos. 2004 Oct;32(10):1096-102. PubMed PMID: 15377641.

13: Nishiyama T, Kawasaki-Yatsugi S, Yamaguchi T, Hanaoka K. Spinal neurotoxicity and tolerance after repeated intrathecal administration of YM 872, an AMPA receptor antagonist, in rats. J Anesth. 2004;18(2):113-7. PubMed PMID: 15127259.

14: Atsumi T, Hoshino S, Furukawa T, Kobayashi S, Asakura T, Takahashi M, Yamamoto Y, Teramoto A. The glutamate AMPA receptor antagonist, YM872, attenuates regional cerebral edema and IgG immunoreactivity following experimental brain injury in rats. Acta Neurochir Suppl. 2003;86:305-7. PubMed PMID: 14753458.

15: Sumikura H, Arendt-Nielsen L. MAC reduction after intrathecal coadministration of GABA(A) agonist and glutamate antagonist in rats. J Anesth. 2003;17(2):92-7. PubMed PMID: 12903919.

16: Furukawa T, Hoshino S, Kobayashi S, Asakura T, Takahashi M, Atsumi T, Teramoto A. The glutamate AMPA receptor antagonist, YM872, attenuates cortical tissue loss, regional cerebral edema, and neurological motor deficits after experimental brain injury in rats. J Neurotrauma. 2003 Mar;20(3):269-78. PubMed PMID: 12820681.

17: Terai K, Suzuki M, Sasamata M, Yatsugi Si, Yamaguchi T, Miyata K. Effect of AMPA receptor antagonist YM872 on cerebral hematoma size and neurological recovery in the intracerebral hemorrhage rat model. Eur J Pharmacol. 2003 Apr 25;467(1-3):95-101. PubMed PMID: 12706461.

18: Hashimoto M, Miyamae T, Yamamoto I, Goshima Y. DOPA cyclohexyl ester potently inhibits aglycemia-induced release of glutamate in rat striatal slices. Neurosci Res. 2003 Mar;45(3):335-44. PubMed PMID: 12631469.

19: Takahashi M, Kohara A, Shishikura J, Kawasaki-Yatsugi S, Ni JW, Yatsugi S, Sakamoto S, Okada M, Shimizu-Sasamata M, Yamaguchi T. YM872: a selective, potent and highly water-soluble alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor antagonist. CNS Drug Rev. 2002 Winter;8(4):337-52. Review. PubMed PMID: 12481190.

20: Suzuki M, Sasamata M, Miyata K. Neuroprotective effects of YM872 coadministered with t-PA in a rat embolic stroke model. Brain Res. 2003 Jan 3;959(1):169-72. PubMed PMID: 12480171.