Page last updated: 2024-11-07

hyoscyamine

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Description

Hyoscyamine: The 3(S)-endo isomer of atropine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(S)-atropine : An atropine with a 2S-configuration. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID154417
CHEMBL ID1234973
CHEMBL ID1331216
CHEMBL ID2449003
CHEBI ID17486
CHEBI ID92712
SCHEMBL ID249586
SCHEMBL ID41316
SCHEMBL ID1649244
MeSH IDM0331322

Synonyms (123)

Synonym
MLS002154242
BRD-K40530731-001-02-5
CHEMBL1234973
tropan-3alpha-yl (2s)-3-hydroxy-2-phenylpropanoate
(-)-hyoscyamine
tropine, (-)-tropate
[3(s)-endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2s)-3-hydroxy-2-phenylpropanoate
CHEBI:17486 ,
(s)-(-)-hyoscyamine
(-)-atropine
(s)-atropine
D00147
hyoscyamine (usp)
PRESTWICK3_000233
hsdb 3552
l-atropine
1-hyoscyamine
hyoscyamine, l-
einecs 202-933-0
benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (3(s)-endo)-
cystospaz
tropine, (-)-tropate (ester)
tropic acid, (-)-, ester with tropine
1alphah,5alphah-tropan-3alpha-ol (-)-tropate (ester)
benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (alphas)-
PRESTWICK_273
NCGC00179608-01
[(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2s)-3-hydroxy-2-phenyl-propanoate
hyoscyamine
benzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (.alpha.s)-
hyoscyamine (l)
BPBIO1_000337
BSPBIO_000305
101-31-5
duboisine
C02046
daturine
l-hyoscyamine ,
l-tropine tropate
OIN ,
(1r,5s)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2r)-3-hydroxy-2-phenylpropanoate
daturin
2ARM
tropine-l-tropate
DB00424
smr000718747
MLS001304011
MLS002222193
HMS2095P07
symax duotab
levsinex sr
symax sr
hyosyne
symax sl
hyospaz
levsin sl
nsc 757064
px44xo846x ,
levbid
unii-px44xo846x
hyoscyamine [usp:ban]
nsc-757064
l-hyopscyamine
hyocyamine
l-hyoscamine
HMS2231N11
benzeneacetic acid, .alpha.-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, (.alpha.s)-
hyoscyaminum [hpus]
hyoscyamine [mart.]
hyoscyamine [hsdb]
hyoscyamine [usp monograph]
hyoscyamine [mi]
hyoscyamine [vandf]
l-tropic acid ester with tropine
hyoscyamine [who-dd]
AKOS015896332
(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2s)-3-hydroxy-2-phenylpropanoate
bellafoline
atropine, (s)-
CHEMBL1331216
hyoscyaminum
CHEMBL2449003
endo-atropine
SCHEMBL249586
CCG-220233
SCHEMBL41316
SCHEMBL1649244
[3(s)-endo]-a-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
RKUNBYITZUJHSG-FXUDXRNXSA-N
AC-34425
J-000364
SR-01000799139-2
sr-01000799139
CHEBI:92712
HMS3712P07
(leo)-hyoscyamine
(s)-(leo)-hyoscyamine
(leo)-atropine
(s)atropine
(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)(2r)-3-hydroxy-2-phenylpropanoate
(3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2s)-3-hydroxy-2-phenylpropanoate
(-)-hyoscyamin
[(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2s)-3-hydroxy-2-phenylpropanoate
Q413762
Q27464129
(2s)-3-hydroxy-2-phenylpropanoic acid [(5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester
F14785
DTXSID20941522
(3beta)-hyoscyamine
912642-93-4
(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2s)-3-hydroxy-2-phenylpropanoate
bdbm50497835
BRD-K40530731-001-11-6
4247B
benzeneacetic acid, alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (alphas)-
DTXSID80889335 ,
AKOS016843532
HYO ,
hyoscyamine dried down 100 microg/ml
AS-75498
benzeneacetic acid, a-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (as)-
[(1s,5r)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] (2s)-3-hydroxy-2-phenyl-propanoate

Research Excerpts

Overview

Hyoscyamine acts as an antagonist of the acetylcholine muscarinic receptor. It can induce a variety of distinct toxic syndromes in mammals (anti-cholinergic poisoning)

ExcerptReferenceRelevance
"Hyoscyamine (HSM), which acts as an antagonist of the acetylcholine muscarinic receptor and can induce a variety of distinct toxic syndromes in mammals (anti-cholinergic poisoning), is hazardous to human health. "( Fluorescence-based immunochromatographic test strip for the detection of hyoscyamine.
Ge, W; Guo, X; Kuang, H; Liu, L; Suryoprabowo, S; Xu, C; Xu, X; Zhu, J, 2022
)
2.4

Treatment

ExcerptReferenceRelevance
"Pretreatment with hyoscyamine sulphate resulted in a significant decrease in the viral load in both chorioallantoic membrane (CAM) and brain tissues at 48 and 96 hours postinfection."( Viral inhibitory potential of hyoscyamine in Japanese encephalitis virus-infected embryonated chicken eggs involving multiple signaling pathways.
Bhattacharjee, A; Karmakar, S; Naga, R; Pal, A; Roy, S; Saha, M, 2023
)
1.52

Toxicity

ExcerptReferenceRelevance
" These alkaloids can be very toxic at high dose."( Atropa belladonna neurotoxicity: Implications to neurological disorders.
Aschner, M; Jiménez, J; Jiménez, JA; Kwakye, GF, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tropane alkaloid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (20)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency8.91250.044717.8581100.0000AID485294
ATAD5 protein, partialHomo sapiens (human)Potency1.03180.004110.890331.5287AID504467
importin subunit beta-1 isoform 1Homo sapiens (human)Potency6.51315.804836.130665.1308AID540253
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency29.93490.168316.404067.0158AID720504
snurportin-1Homo sapiens (human)Potency6.51315.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency6.51315.804816.996225.9290AID540253
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
gemininHomo sapiens (human)Potency0.18360.004611.374133.4983AID624297
[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)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)1,000.00000.11007.190310.0000AID1449628
Muscarinic acetylcholine receptor M2Homo sapiens (human)Ki0.00580.00000.690210.0000AID1185256; AID1185257; AID1185258; AID1185259; AID1185260
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)Ki0.00090.00010.579710.0000AID320532
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)Ki0.00100.00011.48339.1400AID320534
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)Ki0.00060.00010.68688.2600AID320535
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)Ki0.00180.00010.66618.2600AID320536
Muscarinic acetylcholine receptor M5Homo sapiens (human)Ki0.00100.00000.72926.9183AID1063771; AID1185261; AID757595
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)Ki0.00270.00010.58908.2600AID320533
Muscarinic acetylcholine receptor M1Homo sapiens (human)Ki0.00030.00000.59729.1201AID1063776
Muscarinic acetylcholine receptor M3Homo sapiens (human)Ki0.00030.00000.54057.7600AID1063775
[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)
Chain A, Phospholipase A2Daboia russelii pulchellaKd0.02100.021022.510545.0000AID977611
Chain A, Phospholipase A2 VRV-PL-VIIIaDaboia russelii pulchellaKd0.02100.021022.510545.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (60)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
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)
gastric acid secretionMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo sapiens (human)
dopamine transportMuscarinic acetylcholine receptor M5Homo sapiens (human)
transmission of nerve impulseMuscarinic acetylcholine receptor M5Homo sapiens (human)
regulation of phosphatidylinositol dephosphorylationMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMuscarinic acetylcholine receptor M5Homo sapiens (human)
chemical synaptic transmissionMuscarinic acetylcholine receptor M5Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMuscarinic acetylcholine receptor M5Homo 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 (14)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
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)
phosphatidylinositol phospholipase C activityMuscarinic acetylcholine receptor M5Homo sapiens (human)
protein bindingMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled acetylcholine receptor activityMuscarinic acetylcholine receptor M5Homo sapiens (human)
G protein-coupled serotonin receptor activityMuscarinic acetylcholine receptor M5Homo 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 (27)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
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 M5Homo sapiens (human)
postsynaptic membraneMuscarinic acetylcholine receptor M5Homo sapiens (human)
dendriteMuscarinic acetylcholine receptor M5Homo sapiens (human)
plasma membraneMuscarinic acetylcholine receptor M5Homo sapiens (human)
synapseMuscarinic acetylcholine receptor M5Homo 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 (59)

Assay IDTitleYearJournalArticle
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID383538Inhibition of neostigmine-induced neurogenic contractions in New Zealand white rabbit gastric fundus smooth muscle2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Evaluation of myorelaxant activity of 7-substituted hexahydroquinoline derivatives in isolated rabbit gastric fundus.
AID1185258Displacement of [3H]-NMS from human muscarinic M2 Y177Q mutant expressed in Flp-In-CHO cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID1063771Displacement of [3H]QNB from muscarinic M5 receptor (unknown origin)2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds.
AID1133974Antiulcer activity in albino rat pyloric ligation model assessed as elevation of gastric pH at 6.25 mg/kg, po administered as single dose during prior ligation (Rvb =1.1 no_unit)1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Experimental antiulcer drugs. 1. Indole-1-alkanamides and pyrrole-1-alkanamides.
AID1133975Antiulcer activity in albino rat pyloric ligation model assessed as inhibition of gastric volume at 6.25 mg/kg, po administered as single dose 24 hrs prior ligation relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Experimental antiulcer drugs. 1. Indole-1-alkanamides and pyrrole-1-alkanamides.
AID757595Antagonist activity at muscarinic M5 receptor (unknown origin) by PDSP assay2013Bioorganic & medicinal chemistry letters, Jul-01, Volume: 23, Issue:13
Selectivity of phenothiazine cholinesterase inhibitors for neurotransmitter systems.
AID320533Displacement of [3H]NMS from rat muscarinic M2 receptor expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Feb-01, Volume: 18, Issue:3
Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.
AID320536Displacement of [3H]NMS from rat muscarinic M5 receptor expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Feb-01, Volume: 18, Issue:3
Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.
AID1148061Toxicity in iv dosed mouse1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 1. Glycolates.
AID383536Inhibition of electrical field stimulation-induced neurogenic contractions in New Zealand white rabbit gastric fundus smooth muscle2008European journal of medicinal chemistry, Mar, Volume: 43, Issue:3
Evaluation of myorelaxant activity of 7-substituted hexahydroquinoline derivatives in isolated rabbit gastric fundus.
AID1063775Displacement of [3H]QNB from muscarinic M3 receptor (unknown origin)2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds.
AID755993Toxicity in guinea pig ileum assessed as effect on acetylcholine-induced smooth muscle contraction at 0.1 ug/mL after 3 mins (Rvb = 5.17 +/- 0.36 g)2013Bioorganic & medicinal chemistry, Jul-15, Volume: 21, Issue:14
Design, synthesis and biological activity evaluation of desloratadine analogues as H1 receptor antagonists.
AID678721Metabolic stability in human liver microsomes assessed as GSH adduct formation at 100 uM after 90 mins by HPLC-MS analysis2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1185261Displacement of [3H]-NMS from wild-type human muscarinic M5 receptor expressed in CHO-K1 cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID320534Displacement of [3H]NMS from rat muscarinic M3 receptor expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Feb-01, Volume: 18, Issue:3
Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.
AID678712Inhibition of human CYP1A2 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using ethoxyresorufin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1185256Displacement of [3H]-NMS from wild-type human muscarinic M2 receptor expressed in Flp-In-CHO cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID678715Inhibition of human CYP2D6 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 4-methylaminoethyl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1100847Insecticidal activity against fourth-instar larval stage of Bombyx mori Shunrei x Shongetsu assessed as fourth-instar larval duration time at 100 ppm administered through artificial diet (Rvb = 5.1 +/- 0.2 days)2000Bioscience, biotechnology, and biochemistry, Mar, Volume: 64, Issue:3
Synthesis of 2,2-diphenylpropionate derivatives and their effects on larval growth of the silkworm.
AID1063776Displacement of [3H]QNB from muscarinic M1 receptor (unknown origin)2014Bioorganic & medicinal chemistry letters, Jan-15, Volume: 24, Issue:2
The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds.
AID1185257Displacement of [3H]-NMS from human muscarinic M2 Y104A mutant expressed in Flp-In-CHO cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID320532Displacement of [3H]NMS from rat muscarinic M1 receptor expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Feb-01, Volume: 18, Issue:3
Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.
AID678717Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-benzyloxyquinoline as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1148060Anti-tremorine activity against sc dosed albino mouse assessed as normalized dose for reversal of tremorine-induced spontaneous activity depression1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 1. Glycolates.
AID678716Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using diethoxyfluorescein as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1133976Antiulcer activity in albino rat pyloric ligation model assessed as inhibition of total acid output at 6.25 mg/kg, po administered as single dose during ligation relative to control1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Experimental antiulcer drugs. 1. Indole-1-alkanamides and pyrrole-1-alkanamides.
AID678714Inhibition of human CYP2C19 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 3-butyryl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID678722Covalent binding affinity to human liver microsomes assessed per mg of protein at 10 uM after 60 mins presence of NADPH2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID755968Toxicity in guinea pig ileum assessed as effect on acetylcholine-induced smooth muscle spasm at 0.1 ug/mL after 3 mins (Rvb = 1.31 +/- 3.66%)2013Bioorganic & medicinal chemistry, Jul-15, Volume: 21, Issue:14
Design, synthesis and biological activity evaluation of desloratadine analogues as H1 receptor antagonists.
AID678713Inhibition of human CYP2C9 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-methoxy-4-trifluoromethylcoumarin-3-acetic acid as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1185264Antagonist activity at wild-type human muscarinic M2 receptor expressed in Flp-In-CHO cells assessed as inhibition of acetylcholine-induced effect at 0.01 to 100 uM by time-course assay2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID1148059Toxicity in sc dosed albino mouse assessed as mydriasis1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 1. Glycolates.
AID1100848Insecticidal activity against fourth-instar larval stage of Bombyx mori Shunrei x Shongetsu assessed as fourth-instar larval duration time at 30 ppm administered through artificial diet (Rvb = 5.1 +/- 0.2 days)2000Bioscience, biotechnology, and biochemistry, Mar, Volume: 64, Issue:3
Synthesis of 2,2-diphenylpropionate derivatives and their effects on larval growth of the silkworm.
AID320535Displacement of [3H]NMS from rat muscarinic M4 receptor expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Feb-01, Volume: 18, Issue:3
Synthesis and SAR of selective muscarinic acetylcholine receptor subtype 1 (M1 mAChR) antagonists.
AID1185259Displacement of [3H]-NMS from human muscarinic M2 Y177Q/T423H mutant expressed in Flp-In-CHO cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID1185260Displacement of [3H]-NMS from human muscarinic M2 W422A mutant expressed in Flp-In-CHO cells by liquid scintillation counting2014Journal of medicinal chemistry, Aug-14, Volume: 57, Issue:15
Dualsteric muscarinic antagonists--orthosteric binding pose controls allosteric subtype selectivity.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2006Proteins, Jul-01, Volume: 64, Issue:1
Crystal structures of the complexes of a group IIA phospholipase A2 with two natural anti-inflammatory agents, anisic acid, and atropine reveal a similar mode of binding.
AID1811Experimentally measured binding affinity data derived from PDB2006Proteins, Jul-01, Volume: 64, Issue:1
Crystal structures of the complexes of a group IIA phospholipase A2 with two natural anti-inflammatory agents, anisic acid, and atropine reveal a similar mode of binding.
AID129059Analgesic activity as percentage analgesic efficacy on male albino Swiss-Webster mice with the hotplate test; Inactive1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 1. Tropic and 2-phenylpropionic acid esters.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID697852Inhibition of electric eel AChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID697853Inhibition of horse BChE at 2 mg/ml by Ellman's method2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (96)

TimeframeStudies, This Drug (%)All Drugs %
pre-199030 (31.25)18.7374
1990's1 (1.04)18.2507
2000's5 (5.21)29.6817
2010's43 (44.79)24.3611
2020's17 (17.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 105.65

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index105.65 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index5.44 (4.65)
Search Engine Demand Index188.66 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (105.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.01%)5.53%
Reviews6 (6.06%)6.00%
Case Studies2 (2.02%)4.05%
Observational0 (0.00%)0.25%
Other90 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Use of Hyoscyamine Versus Tamsulosin for Management of Ureteral Stent Irritation [NCT03750656]Phase 46 participants (Actual)Interventional2018-11-12Terminated(stopped due to Not accruing patients quickly enough)
Evaluation of the Efficacy of Open Label Placebo in Children With FGIDs (Functional Gastrointestinal Disorders) [NCT02389998]31 participants (Actual)Interventional2014-07-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT02389998 (2) [back to overview]The Primary Outcome Measure Was Mean Daily Pain
NCT02389998 (2) [back to overview]Use of Rescue Medications

The Primary Outcome Measure Was Mean Daily Pain

"Change in mean pain score comparing both treatment arms to the baseline using the Visual analogue scale. (Scale 0-100mm)~The scale reflects severity of the pain going from no pain (0) to maximum pain (100mm). Therefore the higher the number the more severe the pain is" (NCT02389998)
Timeframe: It will be assessed at the end of the 3-week and 6-week treatment periods (at the end of each treatment arm prior to crossover to the next arm of treatment)

Interventionpain scale by VAS in mm (Mean)
Placebo39.9
No Treatment45.14

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Use of Rescue Medications

The number of medications used as rescue during each one of the periods of the study were counted (NCT02389998)
Timeframe: 3 weeks of placebo vs 3 weeks of no treatment

Interventionpill count number (Mean)
Placebo2.0
No Treatment3.8

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