Page last updated: 2024-11-05

edrophonium bromide

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

Edrophonium bromide is a short-acting anticholinesterase agent that is primarily used in the diagnosis and treatment of myasthenia gravis. It acts by inhibiting the breakdown of acetylcholine, a neurotransmitter that plays a role in muscle contraction. This results in increased acetylcholine levels at the neuromuscular junction, leading to improved muscle function. Edrophonium bromide is typically administered intravenously or intramuscularly. Its effects are relatively short-lived, lasting for only a few minutes. The synthesis of edrophonium bromide involves the reaction of 3-hydroxy-N,N-dimethyl-N-(2,2,2-trifluoroethyl)benzamide with ethyl bromide. Edrophonium bromide is studied for its potential therapeutic applications in various conditions, including myasthenia gravis, Alzheimer's disease, and Parkinson's disease. Its importance stems from its ability to enhance cholinergic transmission, which can be beneficial in conditions characterized by reduced acetylcholine activity.'

Cross-References

ID SourceID
PubMed CID9336
CHEMBL ID60745
SCHEMBL ID2462104
MeSH IDM0007058

Synonyms (22)

Synonym
ethyl(m-hydroxyphenyl)dimethylammonium bromide
ammonium, (3-hydroxyphenyl)dimethylethyl-, bromide
tensilon bromide
3-hydroxyphenyldimethylethylammonium bromide
n-ethyl-3-hydroxy-n,n-dimethylbenzenaminium bromide
benzenaminium, n-ethyl-3-hydroxy-n,n-dimethyl-, bromide
oedrophanium
ro 2-3198
ammonium, ethyl(m-hydroxyphenyl)dimethyl-, bromide
edrophonium bromide
CHEMBL60745
edrophone bromide
302-83-0
kx008093vw ,
unii-kx008093vw
benzenaminium, n-ethyl-3-hydroxy-n,n-dimethyl-, bromide (1:1)
edrophonium bromide [mi]
SCHEMBL2462104
ammonium,(3-hydroxyphenyl)dimethylethyl-,bromide
ethyl-(3-hydroxyphenyl)-dimethylazanium;bromide
Q27282472
n-ethyl-3-hydroxy-n,n-dimethylbenzenaminiumbromide

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)1.83990.00000.933210.0000AID31177; AID31496; AID32720
AcetylcholinesteraseHomo sapiens (human)Ki0.00160.00001.27869.7300AID31618
Acetylcholinesterase Bos taurus (cattle)IC50 (µMol)5.36000.00000.61068.7000AID404439
Carboxylic ester hydrolase Equus caballus (horse)Ki340.00000.00200.95708.0000AID44128
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
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)
amyloid-beta bindingAcetylcholinesterase Bos taurus (cattle)
protein bindingAcetylcholinesterase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
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)
synapseAcetylcholinesterase Bos taurus (cattle)
side of membraneAcetylcholinesterase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID44128Compound was evaluated for irreversible inhibition of Horse serum Butyrylcholinesterase1998Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19
Conformationally restricted carbamate inhibitors of horse serum butyrylcholinesterase.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID31177In vitro inhibitory activity against human recombinant AChE2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID404439Inhibition of bovine AChE2008Journal of medicinal chemistry, Jun-12, Volume: 51, Issue:11
Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.
AID31618Inhibition constant determined against Acetylcholinesterase (AChE) receptor.1998Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22
Acetylcholinesterase noncovalent inhibitors based on a polyamine backbone for potential use against Alzheimer's disease.
AID31496Inhibitory activity against Acetylcholinesterase1996Journal of medicinal chemistry, Dec-20, Volume: 39, Issue:26
Structure-based alignment and comparative molecular field analysis of acetylcholinesterase inhibitors.
AID625278FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of no concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID625293Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in LTKB-BD2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID50416Tested for change in heart rate at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID50401Tested for change in LV dp/dt at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID282830Inhibition of human AChE-induced beta amyloid peptide(1-40) aggregation by thioflavin T-based fluorometric assay2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Design, synthesis, and biological evaluation of dual binding site acetylcholinesterase inhibitors: new disease-modifying agents for Alzheimer's disease.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID282831Inhibition of beta amyloid protein 40 aggregation at 100 uM by thioflavin T-based fluorometric assay2005Journal of medicinal chemistry, Nov-17, Volume: 48, Issue:23
Design, synthesis, and biological evaluation of dual binding site acetylcholinesterase inhibitors: new disease-modifying agents for Alzheimer's disease.
AID50426Tested for effect on nictitating membrane at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID50406Tested for change in LV pressure at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID50421Tested for effect on autonomic vagal membrane at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID32720Inhibition acetylcholinesterase (AChE) enzyme.1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 2. Applications.
AID50411Tested for change in arterial pressure at dose of 1.026 umol/kg in cat2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
AID78316In vitro potency in reversing vecuronium-induced block in guinea pig hemidiaphram2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
[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's4 (40.00)18.2507
2000's4 (40.00)29.6817
2010's2 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.16

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 Index17.16 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.16)

All Compounds (24.57)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]