Page last updated: 2024-11-13

evp-6124

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID46196517
CHEMBL ID2151572
SCHEMBL ID744767
MeSH IDM0575646

Synonyms (41)

Synonym
550999-75-2
benzo(b)thiophene-2-carboxamide, n-(3r)-1-azabicyclo(2.2.2)oct-3-yl-7-chloro-
unii-5fi5376a0x
evp6124
evp-6124
encenicline [usan:inn]
5fi5376a0x ,
frm-6124
evp 6124
mt4666
bdbm50393255
mt-4666
CHEMBL2151572 ,
HY-15430
encenicline
CS-0933
n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide
gtpl6926
(r)-7-chloro-n-(quinuclidine-3-yl)benzo[b]thiophene-2-carboxamide
SSRDSYXGYPJKRR-ZDUSSCGKSA-N
SCHEMBL744767
1275596-71-8
encenicline [who-dd]
encenicline [usan]
encenicline [inn]
n-[(3r)-1-azabicyclo[2.2.2]oct-3-yl]-7-chloro-1-benzothiophene-2-carboxamide
(r)-7-chloro-n-(quinuclidin-3-yl)benzo(b)thiophene-2-carboxamide
(r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide
encenicline (usan/inn)
D10626
AKOS027322165
n-(3r)-1-azabicyclo[2.2.2]oct-3-yl-7-chlorobenzo[b]thiophene-2-carboxamide
mfcd23381267
NCGC00378871-01
DB11726
EX-A3984
Q19904062
A913801
I33 ,
7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide
DTXSID701025836

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency37.90830.01237.983543.2770AID1645841
cytochrome P450 2D6Homo sapiens (human)Potency16.93300.00108.379861.1304AID1645840
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)Ki0.00710.00221.742710.0000AID690414; AID709627
5-hydroxytryptamine receptor 3AHomo sapiens (human)IC50 (µMol)0.29900.00011.07899.0000AID690408
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Neuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)EC50 (µMol)0.32670.12802.80188.9000AID1292021; AID1584935; AID1609179
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (41)

Processvia Protein(s)Taxonomy
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to hypoxiaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein phosphorylationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
intracellular calcium ion homeostasisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
signal transductionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synaptic transmission, cholinergicNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
learning or memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
short-term memoryNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of cell population proliferationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of tumor necrosis factor productionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to nicotineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of MAPK cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of angiogenesisNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapse organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
cognitionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
sensory processingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of protein metabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium ion transmembrane transportNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor signaling pathwayNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendritic spine organizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
modulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
dendrite arborizationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of long-term synaptic potentiationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
negative regulation of amyloid-beta formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid precursor protein catabolic processNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to amyloid-betaNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
response to acetylcholineNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of amyloid fibril formationNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of CoA-transferase activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
positive regulation of excitatory postsynaptic potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
regulation of membrane potentialNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chemical synaptic transmissionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 3AHomo sapiens (human)
monoatomic ion transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory postsynaptic potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
inorganic cation transmembrane transport5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 3AHomo sapiens (human)
regulation of membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
amyloid-beta bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
monoatomic ion channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
calcium channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine receptor activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
toxic substance bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
chloride channel regulator activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated monoatomic cation-selective channel activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine bindingNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein homodimerization activityNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-gated monoatomic cation channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 3AHomo sapiens (human)
ligand-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmitter-gated monoatomic ion channel activity involved in regulation of postsynaptic membrane potential5-hydroxytryptamine receptor 3AHomo sapiens (human)
excitatory extracellular ligand-gated monoatomic ion channel activity5-hydroxytryptamine receptor 3AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membrane raftNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynaptic membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
postsynapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
acetylcholine-gated channel complexNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membraneNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
neuron projectionNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
synapseNeuronal acetylcholine receptor subunit alpha-7Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
cleavage furrow5-hydroxytryptamine receptor 3AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
serotonin-activated cation-selective channel complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 3AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 3AHomo sapiens (human)
transmembrane transporter complex5-hydroxytryptamine receptor 3AHomo sapiens (human)
neuron projection5-hydroxytryptamine receptor 3AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1609179Agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocytes assessed as induction of channel current at -90 mV holding potential by two-electrode voltage clamp method2019European journal of medicinal chemistry, Nov-15, Volume: 182Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation.
AID709627Displacement of [3H]epibatidine form human alpha7 nAchR expressed in HEK293 cells2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders.
AID709449Inhibition of human 5HT3R at 10 nM2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders.
AID1292022Binding affinity to human alpha7 nAChR expressed in xenopus oocytes preincubated for 10 mins followed by acetylcholine addition by patch clamp electrophysiological assay relative to acetylcholine2016European journal of medicinal chemistry, Jun-10, Volume: 115Synthesis and biological activities of indolizine derivatives as alpha-7 nAChR agonists.
AID1584935Partial agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocytes by voltage clamp electrophysiological method2018European journal of medicinal chemistry, Dec-05, Volume: 160Discovery, cocrystallization and biological evaluation of novel piperidine derivatives as high affinity Ls-AChBP ligands possessing α7 nAChR activities.
AID1609178Agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocytes assessed as induction of channel current at 10 uM at -90 mV holding potential by two-electrode voltage clamp method relative to acetylcholine2019European journal of medicinal chemistry, Nov-15, Volume: 182Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation.
AID690408Binding affinity to 5HT3 receptor2011Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23
Discovery and development of α7 nicotinic acetylcholine receptor modulators.
AID1609177Agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocytes assessed as induction of channel current at 100 uM at -90 mV holding potential by two-electrode voltage clamp method relative to acetylcholine2019European journal of medicinal chemistry, Nov-15, Volume: 182Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation.
AID1292021Agonist activity at human alpha7 nAChR expressed in xenopus oocytes preincubated for 10 mins followed by acetylcholine addition by patch clamp electrophysiological assay2016European journal of medicinal chemistry, Jun-10, Volume: 115Synthesis and biological activities of indolizine derivatives as alpha-7 nAChR agonists.
AID690414Binding affinity to human alpha7 nAchR2011Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23
Discovery and development of α7 nicotinic acetylcholine receptor modulators.
AID1609180Agonist activity at human alpha7 nAChR expressed in Xenopus laevis oocytes assessed as peak current amplitude at -90 mV holding potential by two-electrode voltage clamp method relative to acetylcholine2019European journal of medicinal chemistry, Nov-15, Volume: 182Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation.
AID1278549Displacement of [3H]methyllycaconitine from Sprague-Dawley rat brain alpha7* nAChR incubated for 2.5 hrs by liquid scintillation counting analysis2016European journal of medicinal chemistry, Mar-03, Volume: 110New quinoline derivatives as nicotinic receptor modulators.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346583Human nicotinic acetylcholine receptor alpha7 subunit (Nicotinic acetylcholine receptors)2011Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23
Discovery and development of α7 nicotinic acetylcholine receptor modulators.
AID1346583Human nicotinic acetylcholine receptor alpha7 subunit (Nicotinic acetylcholine receptors)2004Drugs in R&D, , Volume: 5, Issue:2
Natalizumab: AN 100226, anti-4alpha integrin monoclonal antibody.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (10.00)29.6817
2010's7 (70.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.86

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index24.86 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.62 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]