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
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 |
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| Potentiation of responses to AMPA on central neurones by LY392098 and LY404187 in vivo. | 2001 Jun |
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| Therapeutic approaches to age-associated neurocognitive disorders. | 2001 Sep |
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| Antidepressant activity of memory-enhancing drugs in the reduction of submissive behavior model. | 2002 Apr 5 |
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| 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 |
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| Positive modulators of AMPA receptors as a potential treatment for schizophrenia. | 2002 Jul |
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| Cortex Pharmaceuticals, Inc. Maintaining brain function goes a long way. | 2003 Nov |
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| Modulation of AMPA receptor kinetics differentially influences synaptic plasticity in the hippocampus. | 2004 |
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| A placebo-controlled add-on trial of the Ampakine, CX516, for cognitive deficits in schizophrenia. | 2008 Feb |
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| Glutamate receptor-mediated restoration of experience-dependent place field expansion plasticity in aged rats. | 2008 Jun |
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| Ampakine CX516 ameliorates functional deficits in AMPA receptors in a hippocampal slice model of protein accumulation. | 2008 Nov |
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| Reversal of cognitive deficits by an ampakine (CX516) and sertindole in two animal models of schizophrenia--sub-chronic and early postnatal PCP treatment in attentional set-shifting. | 2009 Nov |
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| Systematic review of pharmacological treatments in fragile X syndrome. | 2009 Oct 13 |
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| 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.
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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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SUBSTANCE RECORD
