WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 522539
CAS#: 161605-73-8
Description: ZK-200775 is a potent AMPA antagonist. ZK 200775 reversibly worsened the neurological condition in patients with acute ischaemic stroke. ZK 200775 exerts significant sedative effects in patients with acute stroke which preclude its further development as a neuroprotective agent in this indication.
MedKoo Cat#: 522539
Name: ZK-200775
CAS#: 161605-73-8
Chemical Formula: C14H15F3N3O6P
Exact Mass: 409.0651
Molecular Weight: 409.26
Elemental Analysis: C, 41.09; H, 3.69; F, 13.93; N, 10.27; O, 23.46; P, 7.57
Synonym: ZK-200775; ZK 200775; ZK200775. 161605-73-8.
IUPAC/Chemical Name: ((7-morpholino-2,3-dioxo-6-(trifluoromethyl)-3,4-dihydroquinoxalin-1(2H)-yl)methyl)phosphonic acid
InChi Key: WZMQMKNCWDCCMT-UHFFFAOYSA-N
InChi Code: InChI=1S/C14H15F3N3O6P/c15-14(16,17)8-5-9-11(6-10(8)19-1-3-26-4-2-19)20(7-27(23,24)25)13(22)12(21)18-9/h5-6H,1-4,7H2,(H,18,21)(H2,23,24,25)
SMILES Code: FC(C1=CC2=C(N(CP(O)(O)=O)C(C(N2)=O)=O)C=C1N3CCOCC3)(F)F
Appearance: Off-white to light brown 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, not in water
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 409.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Yelshanskaya MV, Li M, Sobolevsky AI. Structure of an agonist-bound ionotropic glutamate receptor. Science. 2014 Aug 29;345(6200):1070-4. doi: 10.1126/science.1256508. Epub 2014 Aug 7. PubMed PMID: 25103407; PubMed Central PMCID: PMC4383034.
2: Webb SM, Vollrath-Smith FR, Shin R, Jhou TC, Xu S, Ikemoto S. Rewarding and incentive motivational effects of excitatory amino acid receptor antagonists into the median raphe and adjacent regions of the rat. Psychopharmacology (Berl). 2012 Dec;224(3):401-12. doi: 10.1007/s00213-012-2759-0. Epub 2012 Jun 30. PubMed PMID: 22752328; PubMed Central PMCID: PMC3498528.
3: Bergholz R, Staks T, Rüther K. Effects of the AMPA antagonist ZK 200775 on visual function: a randomized controlled trial. PLoS One. 2010 Aug 12;5(8):e12111. doi: 10.1371/journal.pone.0012111. PubMed PMID: 20711429; PubMed Central PMCID: PMC2920815.
4: Gronier B. Involvement of glutamate neurotransmission and N-methyl-d-aspartate receptor in the activation of midbrain dopamine neurons by 5-HT1A receptor agonists: an electrophysiological study in the rat. Neuroscience. 2008 Oct 28;156(4):995-1004. doi: 10.1016/j.neuroscience.2008.08.033. Epub 2008 Aug 27. PubMed PMID: 18801415.
5: Walters MR, Kaste M, Lees KR, Diener HC, Hommel M, De Keyser J, Steiner H, Versavel M. The AMPA antagonist ZK 200775 in patients with acute ischaemic stroke: a double-blind, multicentre, placebo-controlled safety and tolerability study. Cerebrovasc Dis. 2005;20(5):304-9. Epub 2005 Aug 30. PubMed PMID: 16131799.
6: Kosowski AR, Cebers G, Cebere A, Swanhagen AC, Liljequist S. Nicotine-induced dopamine release in the nucleus accumbens is inhibited by the novel AMPA antagonist ZK200775 and the NMDA antagonist CGP39551. Psychopharmacology (Berl). 2004 Aug;175(1):114-23. Epub 2004 Apr 16. PubMed PMID: 15088078.
7: Elting JW, Sulter GA, Kaste M, Lees KR, Diener HC, Hommel M, Versavel M, Teelken AW, De Keyser J. AMPA antagonist ZK200775 in patients with acute ischemic stroke: possible glial cell toxicity detected by monitoring of S-100B serum levels. Stroke. 2002 Dec;33(12):2813-8. PubMed PMID: 12468775.
8: Smith T, Groom A, Zhu B, Turski L. Autoimmune encephalomyelitis ameliorated by AMPA antagonists. Nat Med. 2000 Jan;6(1):62-6. PubMed PMID: 10613825.
9: Turski L, Huth A, Sheardown M, McDonald F, Neuhaus R, Schneider HH, Dirnagl U, Wiegand F, Jacobsen P, Ottow E. ZK200775: a phosphonate quinoxalinedione AMPA antagonist for neuroprotection in stroke and trauma. Proc Natl Acad Sci U S A. 1998 Sep 1;95(18):10960-5. PubMed PMID: 9724812; PubMed Central PMCID: PMC28003.
