Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H15N3O |
| Molecular Weight | 241.2884 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C(N1CCCCC1)C2=CC=C3N=CC=NC3=C2
InChI
InChIKey=ANDGGVOPIJEHOF-UHFFFAOYSA-N
InChI=1S/C14H15N3O/c18-14(17-8-2-1-3-9-17)11-4-5-12-13(10-11)16-7-6-15-12/h4-7,10H,1-3,8-9H2
| Molecular Formula | C14H15N3O |
| Molecular Weight | 241.2884 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9502831 | https://www.ncbi.nlm.nih.gov/pubmed/19390843 | https://www.ncbi.nlm.nih.gov/pubmed/12438530
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9502831 | https://www.ncbi.nlm.nih.gov/pubmed/19390843 | https://www.ncbi.nlm.nih.gov/pubmed/12438530
CX 516, a compound synthesized by Cortex Pharmaceuticals using Ampakine® technology licensed from the University of California, was in clinical investigations for the treatment of Alzheimer's disease, schizophrenia, fragile X syndrome and autism, and sleep disorders, however, development of this drug candidate has been discontinued. CX 516 had an extremely short halflife in humans, very low potency and failed to show any benefits in phase II studies. The compound did have a good safety profile, reducing concerns about the toxicity of excess glutamate. Cortex subsequently terminated clinical development of CX 516.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys. | 2000 Apr 25 |
|
| Mechanism and impact of allosteric AMPA receptor modulation by the ampakine CX546. | 2001 Nov |
|
| Therapeutic approaches to age-associated neurocognitive disorders. | 2001 Sep |
|
| Randomized, double-blind, placebo-controlled international clinical trial of the Ampakine CX516 in elderly participants with mild cognitive impairment: a progress report. | 2002 Aug-Oct |
|
| Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-type glutamate receptors elicits neuroprotection after trimethyltin exposure in hippocampus. | 2002 Dec 1 |
|
| CX-516 Cortex pharmaceuticals. | 2002 Jul |
|
| Positive modulators of AMPA receptors as a potential treatment for schizophrenia. | 2002 Jul |
|
| Preliminary experience with an ampakine (CX516) as a single agent for the treatment of schizophrenia: a case series. | 2002 Oct 1 |
|
| Cortex Pharmaceuticals, Inc. Maintaining brain function goes a long way. | 2003 Nov |
|
| Modulation of AMPA receptor kinetics differentially influences synaptic plasticity in the hippocampus. | 2004 |
|
| Amphetamine-evoked gene expression in striatopallidal neurons: regulation by corticostriatal afferents and the ERK/MAPK signaling cascade. | 2004 Oct |
|
| Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data. | 2005 Apr |
|
| Positive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor modulators have different impact on synaptic transmission in the thalamus and hippocampus. | 2005 Apr |
|
| Glutamatergic drugs for schizophrenia: a systematic review and meta-analysis. | 2005 Jan 1 |
|
| Glutamate-based therapeutic approaches: ampakines. | 2006 Feb |
|
| Positive modulation of glutamatergic receptors potentiates the suppressive effects of antipsychotics on conditioned avoidance responding in rats. | 2006 Jun |
|
| Effect of CX516, an AMPA-modulating compound, on cognition and behavior in fragile X syndrome: a controlled trial. | 2006 Oct |
|
| A placebo-controlled add-on trial of the Ampakine, CX516, for cognitive deficits in schizophrenia. | 2008 Feb |
|
| Glutamate receptor-mediated restoration of experience-dependent place field expansion plasticity in aged rats. | 2008 Jun |
|
| Systematic review of pharmacological treatments in fragile X syndrome. | 2009 Oct 13 |
|
| Glutamatergic targets for enhancing extinction learning in drug addiction. | 2010 Dec |
|
| Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors reverses sub-chronic PCP-induced deficits in the novel object recognition task in rats. | 2010 Feb 11 |
Patents
Sample Use Guides
In clinical study patients were treated with 900 mg of CX516 three times daily for 4 weeks
Route of Administration:
Oral
Patch-clamp studies were carried out with outside-out patches excised from pyramidal neurons in field CA1 of rats organotypic hippocampal slices. Concentration-response relations for the steady-state current of responses to 800-ms applications of 1 mM L-glutamate was determined using CX546 solutions (50-5000mkM). CX516 did not exceed 30% of the peak current, even at the near-saturating concentration of 5 mM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:47:38 UTC 2023
by
admin
on
Fri Dec 15 15:47:38 UTC 2023
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| Record UNII |
Z5QU38B4V9
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| Record Status |
Validated (UNII)
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| Record Version |
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Z5QU38B4V9
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154235-83-3
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148184
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DB06247
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CX-516
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DTXSID70165574
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