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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
Structure of LICOSTINEL

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)

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Novel NMDA/glycine site antagonists attenuate cocaine-induced behavioral toxicity.
1997 Nov 12
Effects of AMPA/kainate glutamate receptor antagonists on cocaine-induced convulsions and lethality in mice.
1999 Dec 15
Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex.
2000 Jan 28
In vivo neuroprotective effects of ACEA 1021 confirmed by magnetic resonance imaging in ischemic stroke.
2003 Aug 1
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
Patents

Sample Use Guides

Single doses 10 and 30 mgkg
Route of Administration: Intraperitoneal
Name Type Language
LICOSTINEL
INN   MI   USAN  
INN   USAN  
Official Name English
ACEA-1021
Code English
6,7-DICHLORO-1,4-DIHYDRO-5-NITRO-2,3-QUINOXALINEDIONE
Systematic Name English
licostinel [INN]
Common Name English
LICOSTINEL [USAN]
Common Name English
LICOSTINEL [MI]
Common Name English
ACEA1021
Code English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
Code System Code Type Description
FDA UNII
3Z3037LJTC
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
PUBCHEM
5486198
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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EPA CompTox
DTXSID60165346
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
CAS
153504-81-5
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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EVMPD
SUB08503MIG
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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SMS_ID
100000082289
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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ChEMBL
CHEMBL289832
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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INN
7625
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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NCI_THESAURUS
C73248
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY
USAN
II-23
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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WIKIPEDIA
Licostinel
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
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MERCK INDEX
m800
Created by admin on Fri Dec 15 15:44:34 GMT 2023 , Edited by admin on Fri Dec 15 15:44:34 GMT 2023
PRIMARY Merck Index