ENCENICLINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17ClN2OS.ClH
Molecular Weight	357.298
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.ClC1=CC=CC2=C1SC(=C2)C(=O)N[C@H]3CN4CCC3CC4

InChI

InChIKey=OIJYTJGIDVTCFF-ZOWNYOTGSA-N

InChI=1S/C16H17ClN2OS.ClH/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);1H/t13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C16H17ClN2OS
Molecular Weight	320.837
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://adisinsight.springer.com/drugs/800027229
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22085888 | https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/EVP%206124.pdf

Encenicline (EVP-6124; MT-4666) acts as a potent partial and selective agonist at alpha-7 nicotinic acetylcholine receptor. Encenicline significantly improved memory function in animal models. FORUM Pharmaceuticals (formerly EnVivo Pharmaceuticals) is developing encenicline for the treatment of cognition disorders such as schizophrenia and for Alzheimer's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor protein alpha-7 subunit 77 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22085888	Partial Agonist 290		4.33 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://adisinsight.springer.com/drugs/800027229	Primary		Phase III 656	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: http://adisinsight.springer.com/drugs/800027229	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
35.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.66 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.588 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
100 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2800 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
358 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
45.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8890 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
60.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
52.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
60.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25438724	180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered:	ENCENICLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY443011	https://www.001chemical.com/chem/search?q=DY443011
1PlusChem LLC	1P00DBMS	https://www.1pchem.com/search?query=1P00DBMS
AChemBlock	L14548	http://www.achemblock.com/catalogsearch/result/?q=L14548
AK Scientific	3662AH	https://aksci.com/item_detail.php?cat=3662AH
Aceschem	ACS019865	https://www.aceschem.com/catalog/search.do?q=ACS019865
Angene	AGN-PC-0SIPQ4	http://www.angenechemical.com/productshow/AGN-PC-0SIPQ4.html
ApexBio Technology	A3406	https://www.apexbt.com/catalogsearch/result/?q=A3406
ApexBio Technology	A3407	https://www.apexbt.com/catalogsearch/result/?q=A3407
AstaTech	43221	http://astatechinc.com/CPSResult.php?CRNO=43221
BLD Pharm	BD253839	http://www.bldpharm.com/search/Search.html?keyword=BD253839
BLD Pharm	BD351469	http://www.bldpharm.com/search/Search.html?keyword=BD351469
Capot Chemical	33989	https://www.capotchem.com/search.do?q=33989
Chem Scene	CS-1005	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1005
ChemShuttle	170198	https://www.chemshuttle.com/catalogsearch/result/?q=170198
Hairui	HR33017	http://www.hairuichem.com/en/product/search.do?q=HR33017
KeyOrganics	AS-35280	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35280
Lab Network	LN01341862	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341862
Lab Network	LN01341880	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341880
MedChem Express	HY-15430A	https://www.medchemexpress.com/search.html?q=HY-15430A&ft=&fa=&fp=
MolPort	MolPort-042-676-280	https://www.molport.com/shop/molecule-link/MolPort-042-676-280
MolPort	MolPort-044-724-452	https://www.molport.com/shop/molecule-link/MolPort-044-724-452
MolPort	MolPort-046-156-794	https://www.molport.com/shop/molecule-link/MolPort-046-156-794
MolPort	MolPort-047-114-047	https://www.molport.com/shop/molecule-link/MolPort-047-114-047
MolPort	MolPort-047-345-884	https://www.molport.com/shop/molecule-link/MolPort-047-345-884
Molcore	MC443011	http://www.molcore.com/CatMC443011.html
Molnova	M17537	https://www.molnova.com/en/serch-list.html?keywords=M17537
Ryan Scientific	Tenovin-6	https://ryansci.com/products?q=Tenovin-6&list_q=&search_type=exact
TargetMol	T2285	https://www.targetmol.com/search?keyword=T2285
TargetMol	T7193	https://www.targetmol.com/search?keyword=T7193
Toronto Research Chemicals	E555420	https://www.trc-canada.com/product-detail/?CatNum=E555420
eMolecules	300753173	https://orderbb.emolecules.com/search/#?query=300753173
eMolecules	44811312	https://orderbb.emolecules.com/search/#?query=44811312
eMolecules	44811355	https://orderbb.emolecules.com/search/#?query=44811355
eMolecules	56967862	https://orderbb.emolecules.com/search/#?query=56967862
eMolecules	95536188	https://orderbb.emolecules.com/search/#?query=95536188
mcule	MCULE-3802547659	https://mcule.com/MCULE-3802547659/
mcule	MCULE-5162997914	https://mcule.com/MCULE-5162997914/
mcule	MCULE-6471787976	https://mcule.com/MCULE-6471787976/
mcule	MCULE-8172320801	https://mcule.com/MCULE-8172320801/

PubMed

Title	Date	PubMed
Natalizumab: AN 100226, anti-4alpha integrin monoclonal antibody.	2004	15293871
Discovery and development of α7 nicotinic acetylcholine receptor modulators.	2011 Dec 8	21919481
EVP-6124, a novel and selective α7 nicotinic acetylcholine receptor partial agonist, improves memory performance by potentiating the acetylcholine response of α7 nicotinic acetylcholine receptors.	2012 Feb	22085888
Randomized, Double-Blind, Placebo-Controlled Study of Encenicline, an α7 Nicotinic Acetylcholine Receptor Agonist, as a Treatment for Cognitive Impairment in Schizophrenia.	2015 Dec	26089183

Patents

Sample Use Guides

In Vivo Use Guide

Encenicline was well tolerated at single doses up to 180 mg, and doses as low as 1 mg had dose- and time-dependent pharmacodynamic effects on the central nervous system. Results from a phase IIb trial showed that encenicline (2.0mg once daily) significantly improved cognition and clinical function in patients with mild-to-moderate Alzheimer's disease.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:46:38 GMT 2023` Edited by `admin` on `Sat Dec 16 09:46:38 GMT 2023`
Record UNII	VYV1YE9W06
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENCENICLINE HYDROCHLORIDE

Official Name

English

BENZO(B)THIOPHENE-2-CARBOXAMIDE, N-(3R)-1-AZABICYCLO(2.2.2)OCT-3-YL-7-CHLORO-, HYDROCHLORIDE (1:1)

Systematic Name

English

ENCENICLINE HYDROCHLORIDE [USAN]

Common Name

English

BENZO(B)THIOPHENE-2-CARBOXAMIDE, N-(3R)-1-AZABICYCLO(2.2.2)OCT-3-YL-7-CHLORO-, MONOHYDROCHLORIDE

Systematic Name

English

(R)-7-CHLORO-N-(QUINUCLIDIN-3-YL)BENZO(B)THIOPHENE-2-CARBOXAMIDE HYDROCHLORIDE

Systematic Name

English

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide monohydrochloride

Systematic Name

English

EVP-6124 HYDROCHLORIDE

Code

English

Encenicline hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

CAS

550999-74-1