Page last updated: 2024-11-04

neostigmine methylsulfate

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 CID5824
CHEMBL ID211471
CHEBI ID7516
SCHEMBL ID41903
MeSH IDM0014616

Synonyms (146)

Synonym
ar-32
kirkstigmine methyl sulfate
carbamic acid, ester with (m-hydroxyphenyl)trimethylammonium methyl sulfate
stigmosan methyl sulfate
dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfato
(3-hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester
nsc-93753
benzenaminium,n,n-trimethyl-, methyl sulfate
neostigmine methosulfate
neostigmeth
philostigmin methyl sulfate
nsc93753
synstigmine
neostigmine monomethyl sulfate
(m-hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate
proserin
syntostigmin (injection)
prostigmin methyl sulfate
normastigmin
prostigmine methyl sulfate
hodostin
synthostigmine methyl sulfate
proserine methyl sulfate
carbamic acid,n-dimethyl-, 3-(trimethylammonio)phenyl ester, methyl sulfate
wln: 1n1&vor ck1&1&1 &q &osw1
polstigmine
syntostigmin methyl sulfate
[3-(dimethylcarbamoyl)oxyphenyl]trimethylammonium methyl sulfate
ammonium, methyl sulfate, dimethylcarbamate
eustigmin methyl sulfate
vagostigmine methyl sulfate
leostigmine methyl sulfate
tl-1394
syntostigmin
kirkstigmine
sb-23
[3-(dimethylcarbamoxy)phenyl]trimethylammonium methyl sulfate
stigmanol methyl sulfate
syntostigmine methyl sulfate
neoeserine methyl sulfate
AC-6847
MLS001333720
MLS001148660
smr000058592
neostigmine methylsulphate
dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfate
einecs 200-109-5
neostigmine metilsulfate
eustigmin methylsulfate
gd 65
nsc 93753
(3-(dimethylcarbamoxy)phenyl)trimethylammonium methyl sulfate
3-(dimethylcarbamoxy)phenyl trimethylammonium methyl sulfate
(3-(dimethylcarbamoyl)oxyphenyl)trimethylammonium methyl sulfate
benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-, methyl sulfate
carbamic acid, n,n-dimethyl-, 3-dimethylaminophenyl ester, methosulfate
syntostigmin (van)
ammonium, (3-(dimethylcarbamoyloxy)phenyl)trimethyl-, methylsulfate
ccris 3274
carbamic acid, n,n-dimethyl-, 3-(trimethylammonio)phenyl ester, methylsulfate
carbamic acid, dimethyl-, ester with (m-hydroxyphenyl)trimethylammonium methyl sulfate
neostigmine monomethylsulfate
ammonium, (m-hydroxyphenyl)trimethyl-, methyl sulfate, dimethylcarbamate
methylsulfate, neostigmine
C08200
51-60-5
neostigmine methylsulfate
bloxiverz (tn)
neostigmine methylsulfate (jp17/usp)
D00998
neostigmine methyl sulfate
MLS000028383 ,
neostigmini metilsulfas
chebi:7516 ,
HMS500J20
(3-dimethylcarbamoyloxyphenyl)trimethylammonium methyl sulfate
(3-hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate
N0447
CHEMBL211471 ,
proserinum
bloxiverz
neostigmine methylsulfate [usp:jan]
neostigminmetilsulfat
unii-98imh7m386
98imh7m386 ,
[3-[dimethylamino(oxo)methoxy]phenyl]-trimethylammonium; methyl sulfate
A828681
[3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; methyl sulfate
HMS2234E04
FT-0603223
3-[[(dimethylamino)carbonyl]oxy]-n,n,n-trimethylbenzenaminium methyl sulfate
neostigmine metilsulfate [who-ip]
neostigmine methylsulfate component of prevduo
neostigmine methylsulfate [jan]
neostigmine metilsulfate [who-dd]
neostigmine methylsulfate [usp impurity]
benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-, methyl sulphate
neostigmine methylsulfate [green book]
neostigmini metilsulfas [who-ip latin]
prevduo component neostigmine methylsulfate
neostigmine methylsulfate [orange book]
neostigmine methylsulfate [usp-rs]
neostigmine methylsulfate [vandf]
(m-hydroxyphenyl)trimethylammonium methyl sulphate dimethylcarbamate
neostigmine methyl sulfate [mi]
neostigmine metilsulfate [mart.]
neostigmine metilsulfate [ep monograph]
neostigmine methylsulfate [usp monograph]
AKOS015856682
HMS3371E13
CCG-213722
SCHEMBL41903
CS-4698
3-((dimethylcarbamoyl)oxy)-n,n,n-trimethylbenzenaminium methyl sulfate
HY-B1206
neostigmine (methyl sulfate) ,
OPERA_ID_536
mfcd00011796
DTXSID40199003 ,
3-[(dimethylcarbamoyl)oxy]-n,n,n-trimethylanilinium methyl sulfate
neostigmine methyl sulfate, united states pharmacopeia (usp) reference standard
neostigmine methyl sulfate, european pharmacopoeia (ep) reference standard
neostigmine metilsulfate; 3-[(dimethylcarbamoyl)oxy]-n,n,n-trimethylanilinium methyl sulfate
3-(dimethylcarbamoyloxy)-n,n,n-trimethylbenzenaminium methyl sulfate
51-60-5 (methylsulfate)
Q27107519
AS-15291
(3-(dimethylcarbamoyloxy)phenyl)trimethyl-ammoniumethylsulfate
BCP11922
C75419
[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;methyl sulfate
neostigminemethylsulfate
3-[[(dimethylamino)carbonyl]oxy]-n,n,n-trimethylbenzaminium bromide
neostigmine methyl sulphate
EN300-6731072
Z2037281404
neostigmine metilsulfate (mart.)
neostigmine methylsulfate (usp:jan)
neostigmine metilsulfate (ep monograph)
neostigmine methylsulfate (usp impurity)
neostigmine methylsulfate (usp monograph)
neostigmine methysulfate
dtxcid30121494
stiglyn 1:500
neostigmine methylsulfate (usp-rs)
3-(dimethylcarbamoyloxy)-n,n,n-trimethylanilinium methyl sulfate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 3.1.1.8 (cholinesterase) inhibitorAn EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).
[role 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]

Drug Classes (1)

ClassDescription
arylammonium sulfate salt
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency56.23410.044717.8581100.0000AID485294
Smad3Homo sapiens (human)Potency0.31620.00527.809829.0929AID588855
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency6.51310.00419.984825.9290AID504444
[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)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)23.55000.00000.94539.9400AID1815591; AID268585
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)23.05360.00000.933210.0000AID268584; AID491761; AID745544
CholinesteraseEquus caballus (horse)IC50 (µMol)92.70000.00002.22149.4000AID1815593
[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)
[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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation 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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation 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.
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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation 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.
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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID745544Inhibition of acetylcholine esterase (unknown origin) using acetylthiocholine as substrate incubated for 15 mins prior to substrate addition measured after 5 mins by spectrophotometry2013European journal of medicinal chemistry, May, Volume: 63Triazolothiadiazoles and triazolothiadiazines--biologically attractive scaffolds.
AID491761Inhibition of human whole RBC AChE pretreated for 30 mins by Ellman technique2010Bioorganic & medicinal chemistry, Jul-01, Volume: 18, Issue:13
Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine.
AID482623Inhibition of human LAL at 10 uM after 30 mins by fluorescence assay2010Journal of medicinal chemistry, Jul-22, Volume: 53, Issue:14
Thiadiazole carbamates: potent inhibitors of lysosomal acid lipase and potential Niemann-Pick type C disease therapeutics.
AID1815593Inhibition of horse serum BChE incubated for 5 mins by DTNB reagent based Ellman's method2022Journal of natural products, 01-28, Volume: 85, Issue:1
Spatial Distribution and Stability of Cholinesterase Inhibitory Protoberberine Alkaloids from
AID268585Inhibition of electric eel AchE2006Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15
Synthesis and efficacy of 1-[bis(4-fluorophenyl)-methyl]piperazine derivatives for acetylcholinesterase inhibition, as a stimulant of central cholinergic neurotransmission in Alzheimer's disease.
AID268584Inhibition of human serum AchE2006Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15
Synthesis and efficacy of 1-[bis(4-fluorophenyl)-methyl]piperazine derivatives for acetylcholinesterase inhibition, as a stimulant of central cholinergic neurotransmission in Alzheimer's disease.
AID268583Inhibition of rat brain homogenate AchE2006Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15
Synthesis and efficacy of 1-[bis(4-fluorophenyl)-methyl]piperazine derivatives for acetylcholinesterase inhibition, as a stimulant of central cholinergic neurotransmission in Alzheimer's disease.
AID1815591Inhibition of electrical eel AChE using acetylthiocholine chloride as substrate incubated for 5 mins by DTNB reagent based Ellman's method2022Journal of natural products, 01-28, Volume: 85, Issue:1
Spatial Distribution and Stability of Cholinesterase Inhibitory Protoberberine Alkaloids from
AID491763Selectivity ratio of IC50 for human plasma BChE to IC50 for human whole RBC AChE2010Bioorganic & medicinal chemistry, Jul-01, Volume: 18, Issue:13
Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine.
AID1313873Acute toxicity in ip dosed mouse measured after 72 hrs2016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
Novel potent pyridoxine-based inhibitors of AChE and BChE, structural analogs of pyridostigmine, with improved in vivo safety profile.
AID491762Inhibition of human plasma BChE pretreated for 30 mins by Ellman technique2010Bioorganic & medicinal chemistry, Jul-01, Volume: 18, Issue:13
Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (16.67)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 49.89

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

MetricThis Compound (vs All)
Research Demand Index49.89 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index73.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (49.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]