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
Structure for Encenicline (DB11726)
- Weight
- Average: 320.84
Monoisotopic: 320.075012 - Chemical Formula
- C16H17ClN2OS
- Synonyms
- Encenicline
- External IDs
- EVP-6124
- EVP6124
- MT-4666
- MT4666
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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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.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-7 partial agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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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Ingredient UNII CAS InChI Key Encenicline hydrochloride VYV1YE9W06 550999-74-1 OIJYTJGIDVTCFF-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
- External Links
- 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
Phase Status Purpose Conditions Count 3 Completed Treatment Impaired Cognition / Schizophrenia 3 3 Terminated Treatment Alzheimer's Disease (AD) 1 3 Terminated Treatment Alzheimer's Disease (AD) / Dementia 3 2 Completed Treatment Alzheimer's Disease (AD) 1 2 Completed Treatment Alzheimer's Disease (AD) / Central Nervous System Diseases / Cognition 1 2 Completed Treatment Central Nervous System Diseases / Cognition / Schizophrenia 1 2 Terminated Treatment Nicotine Dependence / Smoking, Cessation 1 2 Withdrawn Treatment Alzheimer's Disease (AD) / Cognition / Dementia 1 1 Completed Treatment Alzheimer's Disease (AD) / Central Nervous System Diseases 1 1 Completed Treatment Cardiac Repolarization / Healthy Subjects (HS) 1
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
Property Value Source Water Solubility 0.00872 mg/mL ALOGPS logP 3.33 ALOGPS logP 3.04 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 14.42 ChemAxon pKa (Strongest Basic) 7.28 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 32.34 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 85.93 m3·mol-1 ChemAxon Polarizability 33.79 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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