NAV

CX516

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
CX516
DrugBank Accession Number
DB06247
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 241.2884
Monoisotopic: 241.121512117
Chemical Formula
C14H15N3O
Synonyms
Not Available
External IDs
  • BDP 12
  • BDP-12
  • CX 516
  • CX-516
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Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease, memory loss, autism, neurologic disorders, dementia, schizophrenia and schizoaffective disorders, attention deficit/hyperactivity disorder (ADHD), and sleep disorders.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

CX 516 is a benzylpiperidine AMPAkine, an AMPA (alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) modulator, that enhances the function of glutamate when it binds allosterically to the AMPA receptor channel complex. CX 516 slows receptor deactivation with a longer open time, slower excitatory postsynaptic potential (EPSP) decay and improvement of hippocampal long term potentiation (LTP).

TargetActionsOrganism
UGlutamate receptor 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Ampalex (Cortex Pharmaceuticals Inc.)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-benzoylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
N-acylpiperidines
Direct Parent
N-benzoylpiperidines
Alternative Parents
Quinoxalines / Pyrazines / Benzenoids / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative / Diazanaphthalene / Heteroaromatic compound / Hydrocarbon derivative / N-benzoylpiperidine / Organic nitrogen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-acylpiperidine (CHEBI:34605)
Affected organisms
Not Available

Chemical Identifiers

UNII
Z5QU38B4V9
CAS number
154235-83-3
InChI Key
ANDGGVOPIJEHOF-UHFFFAOYSA-N
InChI
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
IUPAC Name
6-(piperidine-1-carbonyl)quinoxaline
SMILES
O=C(N1CCCCC1)C1=CC2=C(C=C1)N=CC=N2

References

General References
  1. Knapp RJ, Goldenberg R, Shuck C, Cecil A, Watkins J, Miller C, Crites G, Malatynska E: Antidepressant activity of memory-enhancing drugs in the reduction of submissive behavior model. Eur J Pharmacol. 2002 Apr 5;440(1):27-35. [Article]
  2. O'Neill MJ, Witkin JM: AMPA receptor potentiators: application for depression and Parkinson's disease. Curr Drug Targets. 2007 May;8(5):603-20. [Article]
  3. Berry-Kravis E, Krause SE, Block SS, Guter S, Wuu J, Leurgans S, Decle P, Potanos K, Cook E, Salt J, Maino D, Weinberg D, Lara R, Jardini T, Cogswell J, Johnson SA, Hagerman R: Effect of CX516, an AMPA-modulating compound, on cognition and behavior in fragile X syndrome: a controlled trial. J Child Adolesc Psychopharmacol. 2006 Oct;16(5):525-40. [Article]
KEGG Compound
C13675
ChemSpider
130635
BindingDB
50094009
ChEBI
34605
ChEMBL
CHEMBL136800
ZINC
ZINC000000006489
PDBe Ligand
CX5
Wikipedia
CX-516
PDB Entries
4iy5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAlzheimer's Disease (AD) / Dementia1
2CompletedTreatmentAutism Disorder / Fragile X Syndrome1
2CompletedTreatmentMild Cognitive Impairment (MCI)1
2, 3CompletedTreatmentSchizophrenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.831 mg/mLALOGPS
logP1.56ALOGPS
logP1.45Chemaxon
logS-2.5ALOGPS
pKa (Strongest Basic)1.13Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area46.09 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity68.46 m3·mol-1Chemaxon
Polarizability26.13 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-5930000000-284639424da9f9986583
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-0590000000-36b679c101bae69ad082
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-aae5b85ecee7ea6546ce
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-0790000000-5e0a5cadeec1819c83e0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0190000000-c7b6f81a5a7d5d73e63e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1930000000-98ec3998d7fa5064385e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0910000000-d82d86b268473b8afdad
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.7840046
predicted
DarkChem Lite v0.1.0
[M-H]-157.75923
predicted
DeepCCS 1.0 (2019)
[M+H]+165.5443046
predicted
DarkChem Lite v0.1.0
[M+H]+160.11723
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.1027046
predicted
DarkChem Lite v0.1.0
[M+Na]+166.21037
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutamate receptor 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pdz domain binding
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIA1
Uniprot ID
P42261
Uniprot Name
Glutamate receptor 1
Molecular Weight
101505.245 Da

Drug created at March 19, 2008 16:19 / Updated at June 12, 2020 16:52