Encenicline

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

Identification

Generic Name
Encenicline
DrugBank Accession Number
DB11726
Background

Encenicline has been investigated for the treatment of Cognition, Schizophrenia, Alzheimer's Disease, Cardiac Repolarization, and Central Nervous System Diseases.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 320.84
Monoisotopic: 320.075012
Chemical Formula
C16H17ClN2OS
Synonyms
  • Encenicline
External IDs
  • EVP-6124
  • EVP6124
  • MT-4666
  • MT4666

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Encenicline, a selective, orally active, alpha 7 Nicotinic Acetylcholine Receptor agonist (alpha 7 NAchR agonist). Encenicline may have a similar mechanism of action to GTS-21. Auditory sensory gating, a biological measurement of the ability to suppress the evoked response to the second of two auditory stimuli, is diminished in people with schizophrenia. Deficits in sensory gating are associated with attentional impairment, and may contribute to cognitive symptoms and perceptual disturbances. This inhibitory process, which involves the alpha(7) nicotinic receptor mediated release of gamma-aminobutyric acid (GABA) by hippocampal interneurons, represents a potential new target for therapeutic intervention in schizophrenia.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-7
partial agonist
Humans
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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Product Ingredients
IngredientUNIICASInChI Key
Encenicline hydrochlorideVYV1YE9W06550999-74-1OIJYTJGIDVTCFF-ZOWNYOTGSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiophenes
Sub Class
1-benzothiophenes
Direct Parent
1-benzothiophenes
Alternative Parents
Thiophene carboxamides / Quinuclidines / 2,3,5-trisubstituted thiophenes / 2-heteroaryl carboxamides / Piperidines / Aryl chlorides / Benzenoids / Heteroaromatic compounds / Trialkylamines / Secondary carboxylic acid amides
show 6 more
Substituents
1-benzothiophene / 2,3,5-trisubstituted thiophene / 2-heteroaryl carboxamide / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5FI5376A0X
CAS number
550999-75-2
InChI Key
SSRDSYXGYPJKRR-ZDUSSCGKSA-N
InChI
InChI=1S/C16H17ClN2OS/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19/h1-3,8,10,13H,4-7,9H2,(H,18,20)/t13-/m0/s1
IUPAC Name
N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide
SMILES
ClC1=C2SC(=CC2=CC=C1)C(=O)N[C@H]1CN2CCC1CC2

References

General References
Not Available
PubChem Compound
46196517
PubChem Substance
347828087
ChemSpider
28637768
BindingDB
50393255
ChEMBL
CHEMBL2151572
ZINC
ZINC000095579362
PDBe Ligand
I33
Wikipedia
Encenicline
PDB Entries
7ekp / 7ekt

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCognitive Impairment (CI) / Schizophrenia3
3TerminatedTreatmentAlzheimer's Disease (AD)1
3TerminatedTreatmentAlzheimer's Disease (AD) / Dementia3
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAlzheimer's Disease (AD) / Central Nervous System Disorder / Cognitive Functioning1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00872 mg/mLALOGPS
logP3.33ALOGPS
logP3.04Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.42Chemaxon
pKa (Strongest Basic)7.28Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area32.34 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity85.93 m3·mol-1Chemaxon
Polarizability33.79 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
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-MSsplash10-0006-1900000000-2f243969a832e345140b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-bc3be561aa2094d1fe05
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1009000000-8353ecb8da6a1a3bba6d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-5e04887ef7d11fd79cfd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-2914000000-a84d93327a5cf2aeec86
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03du-0940000000-7b44dedf36eeeffd6909
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9400000000-a7dc9635a29fc875fdf9
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]-167.2421
predicted
DeepCCS 1.0 (2019)
[M+H]+169.60017
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.69331
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial agonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Barbier AJ, Hilhorst M, Van Vliet A, Snyder P, Palfreyman MG, Gawryl M, Dgetluck N, Massaro M, Tiessen R, Timmerman W, Hilt DC: Pharmacodynamics, pharmacokinetics, safety, and tolerability of encenicline, a selective alpha7 nicotinic receptor partial agonist, in single ascending-dose and bioavailability studies. Clin Ther. 2015 Feb 1;37(2):311-24. doi: 10.1016/j.clinthera.2014.09.013. Epub 2014 Oct 14. [Article]

Drug created at October 20, 2016 20:42 / Updated at February 21, 2021 18:53