Page last updated: 2024-11-12

xanthostigmine

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

Description

xanthostigmine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10765787
CHEMBL ID340427
MeSH IDM0536695

Synonyms (5)

Synonym
3-{[methyl({3-[(9-oxo-9h-xanthen-3-yl)oxy]propyl})amino]methyl}phenyl n-methylcarbamate
xanthostigmine
chembl340427 ,
bdbm10692
[3-[[methyl-[3-(9-oxoxanthen-3-yl)oxypropyl]amino]methyl]phenyl] n-methylcarbamate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)6.88470.00001.559910.0000AID1796503; AID1796566; AID1916856; AID241042; AID283852
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)0.03620.00000.933210.0000AID1796503; AID1796566; AID1916855; AID241106; AID283851; AID31020; AID314091; AID482894; AID669786
Adenosine receptor A1Bos taurus (cattle)IC50 (µMol)0.00030.00001.09106.7400AID283851
AcetylcholinesteraseRattus norvegicus (Norway rat)IC50 (µMol)0.01510.00020.52597.2000AID32107; AID32108
Carboxylic ester hydrolase Rattus norvegicus (Norway rat)IC50 (µMol)0.04800.00041.48119.8700AID44445
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Bos taurus (cattle)
response to purine-containing compoundAdenosine receptor A1Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID482894Inhibition of AChE2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
Prediction of acetylcholinesterase inhibitors and characterization of correlative molecular descriptors by machine learning methods.
AID32107Inhibition of rat acetylcholinesterase (AChE)1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.
AID230415It is the ratio of IC50 for butyrl cholinesterase (BuChE ) to that of acetylcholinesterase (AChE)1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.
AID314091Inhibition of human AchE2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Multi-target-directed ligands to combat neurodegenerative diseases.
AID283853Ratio of IC50 for BuChE to IC50 for AchE2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones.
AID314093Inhibition of human AchE-induced amyloid beta aggregation at 100 uM2008Journal of medicinal chemistry, Feb-14, Volume: 51, Issue:3
Multi-target-directed ligands to combat neurodegenerative diseases.
AID31020In vitro inhibition of human erythrocyte Acetylcholinesterase.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Acetylcholinesterase inhibitors: SAR and kinetic studies on omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl derivatives.
AID1916856Inhibition of human serum BChE using butyrylthiocholine as substrate by Ellman's method2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID241042Inhibition of isolated human BuChE2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
AID283852Inhibition of human serum BuChE2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones.
AID242939Ratio of IC50 for human BuChE and AChE2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
AID241106Inhibition of recombinant human AChE2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
AID283851Inhibition of human erythrocyte AchE2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones.
AID1916855Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate by Ellman's method2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID44445Inhibition of isolated Butyrylcholinesterase (BuChE )1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.
AID252039Inhibition of human AChE induced beta-amyloid aggregation in thioflavin T-based fluorometric assay2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
AID283854Ratio of IC50 for AchE to IC50 for BuChE2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones.
AID669786Inhibition of human AChE2012ACS medicinal chemistry letters, Mar-08, Volume: 3, Issue:3
The First Dual ChE/FAAH Inhibitors: New Perspectives for Alzheimer's Disease?
AID32108Inhibitory concentration against rat brain acetylcholinesterase AChE1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.
AID1916857Selectivity index, ratio of IC50 for human serum BChE to IC50 for human erythrocyte AChE2022European journal of medicinal chemistry, Oct-05, Volume: 240Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease.
AID1796566Cholinesterase Inhibition Assay from Article 10.1021/jm9810046: \\Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.\\1998Journal of medicinal chemistry, Oct-08, Volume: 41, Issue:21
Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives.
AID1796503Cholinesterase Inhibition Assay from Article 10.1021/jm049515h: \\Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.\\2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
AID493017Wombat Data for BeliefDocking2005Journal of medicinal chemistry, Jun-30, Volume: 48, Issue:13
Cholinesterase inhibitors: xanthostigmine derivatives blocking the acetylcholinesterase-induced beta-amyloid aggregation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's5 (55.56)29.6817
2010's2 (22.22)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.89

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.89 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.19 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (22.22%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (77.78%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]