Encenicline

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

Identification

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Name
Encenicline
Accession Number
DB11726  (DB06341)
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
External IDs
EVP-6124 / EVP6124 / MT-4666 / MT4666
Product Ingredients
IngredientUNIICASInChI Key
Encenicline hydrochlorideVYV1YE9W06550999-74-1OIJYTJGIDVTCFF-ZOWNYOTGSA-N
Categories
UNII
5FI5376A0X
CAS number
550999-75-2
Weight
Average: 320.84
Monoisotopic: 320.075012
Chemical Formula
C16H17ClN2OS
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
46196517
PubChem Substance
347828087
ChemSpider
28637768
BindingDB
50393255
ChEMBL
CHEMBL2151572
Wikipedia
Encenicline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAlzheimer's Disease (AD) / Central Nervous System Diseases1
1CompletedTreatmentCardiac Repolarization / Healthy Volunteers1
1CompletedTreatmentCentral Nervous System Diseases / Schizoaffective Disorders / Schizophrenic Disorders1
1CompletedTreatmentHepatic Impairment1
1CompletedTreatmentImpaired Renal Function1
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAlzheimer's Disease (AD) / Central Nervous System Diseases / Cognition1
2CompletedTreatmentCentral Nervous System Diseases / Cognition / Schizophrenic Disorders1
2TerminatedTreatmentCessation, Smoking / Nicotine Dependence1
2WithdrawnTreatmentAlzheimer's Disease (AD) / Cognition / Dementias1
3CompletedTreatmentImpaired Cognition / Schizophrenic Disorders3
3TerminatedTreatmentAlzheimer's Disease (AD)1
3TerminatedTreatmentAlzheimer's Disease (AD) / Dementias3

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Quinuclidine / Thiophene carboxamide / Thiophene carboxylic acid or derivatives / 2,3,5-trisubstituted thiophene / 2-heteroaryl carboxamide / Piperidine / Benzenoid / Aryl halide / Aryl chloride
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. [PubMed:25438724]

Drug created on October 20, 2016 14:42 / Updated on June 04, 2019 07:26