Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H3Cl2N3O4 |
Molecular Weight | 276.033 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+](=O)C1=C2NC(=O)C(=O)NC2=CC(Cl)=C1Cl
InChI
InChIKey=CHFSOFHQIZKQCR-UHFFFAOYSA-N
InChI=1S/C8H3Cl2N3O4/c9-2-1-3-5(6(4(2)10)13(16)17)12-8(15)7(14)11-3/h1H,(H,11,14)(H,12,15)
Licostinel (ACEA 1021) is a potent competitive antagonist at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. The robust efficacy of glycine/NMDA antagonists, such as ACEA 1021, in animal model of brain ischemia, together with good safety profile in animal models and in clinical trials, suggested that this class of NMDA antagonists should have good chance of success in the clinic as neuroprotectants. The clinical trial of ACEA 1021 for stroke was discontinued, mainly due to low solubility and lack of metabolism of the drug that led to the observation of crystals in the urine of some of the patients. In vivo ACEA 1021 reduced the rate of propagation of cortical spreading depression, an effect consistent with blockade of NMDA receptors. ACEA 1021 also decreased audiogenic myoclonus in resuscitated rats following cardiac arrest, and the minimum alveolar concentration for halothane, effects which suggest a reduction of excitatory amino acid neurotransmission. ACEA 1021 crosses the blood-brain barrier and blocks the pathophysiologic consequences of NMDA receptor overstimulation. It was neuroprotective with a favorable therapeutic window in models of transient and permanent cerebral ischemia, epilepsy and pain.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Novel NMDA/glycine site antagonists attenuate cocaine-induced behavioral toxicity. | 1997 Nov 12 |
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Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice. | 1999 Dec 15 |
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Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex. | 2000 Jan 28 |
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In vivo neuroprotective effects of ACEA 1021 confirmed by magnetic resonance imaging in ischemic stroke. | 2003 Aug 1 |
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Delayed treatment with 5-nitro-6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione, a glycine site N-methyl-D-aspartate antagonist, protects against permanent middle cerebral artery occlusion in male rats. | 2003 Aug 28 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15592582
Single doses 10 and 30 mgkg
Route of Administration:
Intraperitoneal
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NCI_THESAURUS |
C1509
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3Z3037LJTC
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5486198
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153504-81-5
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SUB08503MIG
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100000082289
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CHEMBL289832
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7625
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C73248
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II-23
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Licostinel
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m800
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ACTIVE MOIETY