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 |
|---|---|---|
| Glutamatergic targets for enhancing extinction learning in drug addiction. | 2010-12 |
|
| 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. | 2010-02-11 |
|
| 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. | 2009-11 |
|
| Systematic review of pharmacological treatments in fragile X syndrome. | 2009-10-13 |
|
| Ampakine CX516 ameliorates functional deficits in AMPA receptors in a hippocampal slice model of protein accumulation. | 2008-11 |
|
| Glutamate receptor-mediated restoration of experience-dependent place field expansion plasticity in aged rats. | 2008-06 |
|
| A placebo-controlled add-on trial of the Ampakine, CX516, for cognitive deficits in schizophrenia. | 2008-02 |
|
| Effect of CX516, an AMPA-modulating compound, on cognition and behavior in fragile X syndrome: a controlled trial. | 2006-10 |
|
| Positive modulation of glutamatergic receptors potentiates the suppressive effects of antipsychotics on conditioned avoidance responding in rats. | 2006-06 |
|
| Glutamate-based therapeutic approaches: ampakines. | 2006-02 |
|
| Therapeutic potential of positive AMPA modulators and their relationship to AMPA receptor subunits. A review of preclinical data. | 2005-04 |
|
| Positive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor modulators have different impact on synaptic transmission in the thalamus and hippocampus. | 2005-04 |
|
| Glutamatergic drugs for schizophrenia: a systematic review and meta-analysis. | 2005-01-01 |
|
| Amphetamine-evoked gene expression in striatopallidal neurons: regulation by corticostriatal afferents and the ERK/MAPK signaling cascade. | 2004-10 |
|
| Modulation of AMPA receptor kinetics differentially influences synaptic plasticity in the hippocampus. | 2004 |
|
| Cortex Pharmaceuticals, Inc. Maintaining brain function goes a long way. | 2003-11 |
|
| Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-type glutamate receptors elicits neuroprotection after trimethyltin exposure in hippocampus. | 2002-12-01 |
|
| Benzamide-type AMPA receptor modulators form two subfamilies with distinct modes of action. | 2002-12 |
|
| Preliminary experience with an ampakine (CX516) as a single agent for the treatment of schizophrenia: a case series. | 2002-10-01 |
|
| Randomized, double-blind, placebo-controlled international clinical trial of the Ampakine CX516 in elderly participants with mild cognitive impairment: a progress report. | 2002-09-06 |
|
| CX-516 Cortex pharmaceuticals. | 2002-07 |
|
| Positive modulators of AMPA receptors as a potential treatment for schizophrenia. | 2002-07 |
|
| Antidepressant activity of memory-enhancing drugs in the reduction of submissive behavior model. | 2002-04-05 |
|
| Survival signaling and selective neuroprotection through glutamatergic transmission. | 2002-03 |
|
| Mechanism and impact of allosteric AMPA receptor modulation by the ampakine CX546. | 2001-11 |
|
| A placebo-controlled pilot study of the ampakine CX516 added to clozapine in schizophrenia. | 2001-10 |
|
| Therapeutic approaches to age-associated neurocognitive disorders. | 2001-09 |
|
| Positive modulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors in prefrontal cortical pyramidal neurons by a novel allosteric potentiator. | 2001-07 |
|
| Potentiation of responses to AMPA on central neurones by LY392098 and LY404187 in vivo. | 2001-06 |
|
| Novel AMPA receptor potentiators LY392098 and LY404187: effects on recombinant human AMPA receptors in vitro. | 2001-06 |
|
| AMPA receptor blockade improves levodopa-induced dyskinesia in MPTP monkeys. | 2000-04-25 |
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
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