Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H24ClFN4O |
| Molecular Weight | 462.946 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CC1=CC=CC(\C=C\C2=NC3=C(C=C(F)C=C3)C(=O)N2C4=CC=CC=C4Cl)=N1
InChI
InChIKey=HYHNPUGUPISSQO-FYWRMAATSA-N
InChI=1S/C26H24ClFN4O/c1-3-31(4-2)17-20-9-7-8-19(29-20)13-15-25-30-23-14-12-18(28)16-21(23)26(33)32(25)24-11-6-5-10-22(24)27/h5-16H,3-4,17H2,1-2H3/b15-13+
| Molecular Formula | C26H24ClFN4O |
| Molecular Weight | 462.946 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12511770 | https://www.ncbi.nlm.nih.gov/pubmed/11093768Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11804610 | https://www.ncbi.nlm.nih.gov/pubmed/11206453
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12511770 | https://www.ncbi.nlm.nih.gov/pubmed/11093768
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11804610 | https://www.ncbi.nlm.nih.gov/pubmed/11206453
CP-465022 is a potent, and selective noncompetitive AMPA receptor antagonist. It provides neuroprotective efficacy after cerebral ischemia on the basis of the activity in experimental ischemia models. CP-465022 inhibits AMPA receptor-mediated whole cell currents in rat cortical neurons in primary culture with an IC50 value of 30 nM but only weakly inhibits NMDA, g-aminobutyric acid, or kainate receptor-mediated currents. CP-465022 binds to the AMPA receptor with high affinity (IC50 = 36 nM) and displays potent anticonvulsant activity. The compound does not discriminate among AMPA receptors composed of different homomeric or heteromeric subunit
combinations. Furthermore, CP-465022 inhibits AMPA receptor activity in a noncompetitive manner that is neither voltage- nor use-dependent. When administered to rodents
systemically, CP-465022 inhibits AMPA receptor-mediated synaptic transmission and chemically induced seizures.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| CP-465,022, a selective noncompetitive AMPA receptor antagonist, blocks AMPA receptors but is not neuroprotective in vivo. | 2003-01 |
|
| Atropisomeric quinazolin-4-one derivatives are potent noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists. | 2001-01-22 |
|
| Characterization of the binding site for a novel class of noncompetitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor antagonists. | 2000-12 |
Patents
Sample Use Guides
Rats: CP-465022 efficaciously and reversibly decreased
the amplitude of the evoked population spike. When administered as a 1-minute intravenous infusion,
this effect was dose dependent. Maximal inhibition
was at 1 mg/kg, which reversed within approximately 30
minutes. After subcutaneous administration, inhibition was
maintained for much longer periods. Maximum
inhibition was observed at 15 mg/kg SC of racemic CP-
465,022 (equivalent to 7.5 mg/kg of the resolved S enantiomer).
Route of Administration:
Other
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
4582JTR93Y
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| Record Status |
Validated (UNII)
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| Record Version |
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