Compounds > 5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-10,11-dihydrobenzo(b,e)(1,4)diazepine-11-one
Page last updated: 2024-09-27

5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-10,11-dihydrobenzo(b,e)(1,4)diazepine-11-one

Description

5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-10,11-dihydrobenzo(b,e)(1,4)diazepine-11-one: structure given in first source; a dibenzo derivative of AQ-RA 741; a m2-selective muscarinic antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID372625
CHEMBL ID295388
SCHEMBL ID12648694
MeSH IDM0207714

Synonyms (14)

Synonym
142860-99-9
5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-10,11-dihydrobenzo(b,e)(1,4)diazepine-11-one
5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-5,10-dihydro-11h-dibenzo(b,c)(1,4)diazepin-11-one
5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one
11-[2-[4-[4-(diethylamino)butyl]-1-piperidyl]acetyl]-5h-benzo[b][1,4]benzodiazepin-6-one
NCI60_016667
nsc-648064
nsc648064
CHEMBL295388 ,
11-[2-[4-[4-(diethylamino)butyl]piperidin-1-yl]acetyl]-5h-benzo[b][1,4]benzodiazepin-6-one
11h-dibenzo(b,c)(1,4)diazepin-11-one, 5-((4-(4-(diethylamino)butyl)-1-piperidinyl)acetyl)-5,10-dihydro-
SCHEMBL12648694
DTXSID50162203
bdbm50230694

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M2Homo sapiens (human)Ki0.00030.00000.690210.0000AID1756787
Muscarinic acetylcholine receptor M4Homo sapiens (human)Ki0.00200.00000.79519.1201AID1710667; AID1756789
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)Ki0.00030.00010.58908.2600AID1598785
Muscarinic acetylcholine receptor M1Homo sapiens (human)Ki0.00310.00000.59729.1201AID1598784; AID1710664; AID1710665; AID1756786
Muscarinic acetylcholine receptor M3Homo sapiens (human)Ki0.01000.00000.54057.7600AID1598786; AID1710666; AID1756788
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M2Homo sapiens (human)
regulation of heart contractionMuscarinic acetylcholine receptor M2Homo sapiens (human)
response to virusMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionMuscarinic acetylcholine receptor M2Homo sapiens (human)
regulation of smooth muscle contractionMuscarinic acetylcholine receptor M2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M2Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M2Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M4Homo sapiens (human)
cell surface receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
regulation of locomotionMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M4Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M4Homo sapiens (human)
positive regulation of monoatomic ion transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
neuromuscular synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of locomotionMuscarinic acetylcholine receptor M1Homo sapiens (human)
saliva secretionMuscarinic acetylcholine receptor M1Homo sapiens (human)
cognitionMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of postsynaptic membrane potentialMuscarinic acetylcholine receptor M1Homo sapiens (human)
regulation of glial cell proliferationMuscarinic acetylcholine receptor M1Homo sapiens (human)
positive regulation of intracellular protein transportMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic modulation of chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M1Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M1Homo sapiens (human)
calcium-mediated signalingMuscarinic acetylcholine receptor M3Homo sapiens (human)
regulation of monoatomic ion transmembrane transporter activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
signal transductionMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
synaptic transmission, cholinergicMuscarinic acetylcholine receptor M3Homo sapiens (human)
nervous system developmentMuscarinic acetylcholine receptor M3Homo sapiens (human)
positive regulation of insulin secretionMuscarinic acetylcholine receptor M3Homo sapiens (human)
protein modification processMuscarinic acetylcholine receptor M3Homo sapiens (human)
positive regulation of smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
saliva secretionMuscarinic acetylcholine receptor M3Homo sapiens (human)
acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
ion channel modulating, G protein-coupled receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
ligand-gated ion channel signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
regulation of smooth muscle contractionMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M3Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M3Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M2Homo sapiens (human)
arrestin family protein bindingMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M2Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M4Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M4Homo sapiens (human)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M1Homo sapiens (human)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
signaling receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
acetylcholine bindingMuscarinic acetylcholine receptor M3Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
plasma membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
clathrin-coated endocytic vesicle membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
asymmetric synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
symmetric synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
presynaptic membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
neuronal cell bodyMuscarinic acetylcholine receptor M2Homo sapiens (human)
axon terminusMuscarinic acetylcholine receptor M2Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
glutamatergic synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
cholinergic synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M2Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M2Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M2Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M4Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M4Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M4Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
presynaptic membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
axon terminusMuscarinic acetylcholine receptor M1Homo sapiens (human)
Schaffer collateral - CA1 synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
postsynaptic density membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
glutamatergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
cholinergic synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M1Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M1Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M1Homo sapiens (human)
endoplasmic reticulum membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
basal plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
basolateral plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M3Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M3Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1756786Displacement of [3H]-NMS from human muscarinic M1 receptor expressed in CHO cell membranes assessed as inhibition constant by radioligand competition analysis
AID1598784Displacement of [3H]-NMS from muscarinic M1 receptor (unknown origin) expressed in mouse A9L cells after 60 mins by scintillation counting method
AID1598788Selectivity ratio of Ki for muscarinic M1 receptor (unknown origin) expressed in mouse A9L cell membranes to Ki for rat heart muscarinic M2 receptor
AID1710666Displacement of [3H]-NMS from muscarinic M3 receptor (unknown origin) expressed in A9 cells by scintillation counting analysis
AID225361Binding affinity by the displacement of [3H]NMS binding to A9 L cells transfected with muscarinic M1 receptor of rat brain1993Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1
Synthesis and structure-activity relationship of some 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]-10,11-dihydro-5H- benzo[b,e][1,4]diazepin-11-ones as M2-selective antimuscarinics.
AID1756788Displacement of [3H]-NMS from human muscarinic M3 receptor expressed in CHO cell membranes assessed as inhibition constant by radioligand competition analysis
AID1756791Selectivity index, ratio of pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M4 expressed in CHO cell membranes to pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M2 expressed in CHO cell membranes
AID225367Binding affinity by the displacement of [3H]NMS binding to muscarinic M2 receptor of rat heart1993Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1
Synthesis and structure-activity relationship of some 5-[[[(dialkylamino)alkyl]-1-piperidinyl]acetyl]-10,11-dihydro-5H- benzo[b,e][1,4]diazepin-11-ones as M2-selective antimuscarinics.
AID1756784Selectivity index, ratio of pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M3 expressed in CHO cell membranes to pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M2 expressed in CHO cell membranes
AID1598789Selectivity ratio of Ki for muscarinic M3 receptor (unknown origin) expressed in mouse A9L cell membranes to Ki for rat heart muscarinic M2 receptor
AID1598785Displacement of [3H]-NMS from rat heart muscarinic M2 receptor after 60 mins by scintillation counting method
AID1598790Selectivity ratio of Ki for muscarinic M4 receptor in mouse/rat NG108-15 cells to Ki for rat heart muscarinic M2 receptor
AID1710664Displacement of [3H]-NMS from muscarinic M1 receptor (unknown origin) expressed in A9 cells by scintillation counting analysis
AID1598786Displacement of [3H]-NMS from muscarinic M3 receptor (unknown origin) expressed in mouse A9L cell membranes after 60 mins by scintillation counting method
AID1756787Displacement of [3H]-NMS from human muscarinic M2 receptor expressed in CHO cell membranes assessed as inhibition constant by radioligand competition analysis
AID1598787Displacement of [3H]-NMS from muscarinic M4 receptor in mouse/rat NG108-15 cells after 60 mins by scintillation counting method
AID1756789Displacement of [3H]-NMS from human muscarinic M4 receptor expressed in CHO cell membranes assessed as inhibition constant by radioligand competition analysis
AID1756785Selectivity index, ratio of pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M1 expressed in CHO cell membranes to pKi for displacement of [3H]NMS from human recombinant muscarinic receptor M2 expressed in CHO cell membranes
AID1710665Displacement of [3H]-NMS from muscarinic M2 receptor (unknown origin) expressed in A9 cells by scintillation counting analysis
AID1710667Displacement of [3H]-NMS from muscarinic M4 receptor (unknown origin) expressed in NG108-15 cells by scintillation counting analysis
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (42.86)18.2507
2000's0 (0.00)29.6817
2010's2 (28.57)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceDescriptionRelationhip StrengthStudiesTrialsClassesRoles
afdx 116[no description available]medium10benzodiazepine
aq-ra 741[no description available]medium20benzodiazepine
carbachol[no description available]medium10ammonium salt;
carbamate ester		cardiotonic drug;
miotic;
muscarinic agonist;
nicotinic acetylcholine receptor agonist;
non-narcotic analgesic
afdx 384[no description available]medium10benzodiazepine
bibn 99[no description available]medium10
atropine[no description available]medium10
piperidines[no description available]medium40
n-methylscopolamine[no description available]medium10
chlorine[no description available]medium10halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
pirenzepine[no description available]medium10pyridobenzodiazepineanti-ulcer drug;
antispasmodic drug;
muscarinic antagonist
ConditionIndicatedRelationship StrengthStudiesTrials