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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 of ENCENICLINE HYDROCHLORIDE

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
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.

Originator

Curator's Comment: # Bayer HealthCare

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.33 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
35.6 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2800 ng × h/mL
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
63 h
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
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
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
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Natalizumab: AN 100226, anti-4alpha integrin monoclonal antibody.
2004
Discovery and development of α7 nicotinic acetylcholine receptor modulators.
2011 Dec 8
Randomized, Double-Blind, Placebo-Controlled Study of Encenicline, an α7 Nicotinic Acetylcholine Receptor Agonist, as a Treatment for Cognitive Impairment in Schizophrenia.
2015 Dec
Patents

Sample Use Guides

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 UTC 2023
Edited
by admin
on Sat Dec 16 09:46:38 UTC 2023
Record UNII
VYV1YE9W06
Record Status Validated (UNII)
Record Version
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Name Type Language
ENCENICLINE HYDROCHLORIDE
USAN   WHO-DD  
USAN  
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
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
FDA UNII
VYV1YE9W06
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL2151572
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
SMS_ID
300000044458
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
USAN
ZZ-157
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
NCI_THESAURUS
C169947
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
PUBCHEM
46208542
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID40673090
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
DRUG BANK
DBSALT002058
Created by admin on Sat Dec 16 09:46:39 UTC 2023 , Edited by admin on Sat Dec 16 09:46:39 UTC 2023
PRIMARY
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