Page last updated: 2024-12-06

butyrylthiocholine

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

Description

Butyrylthiocholine is a synthetic analog of acetylcholine, a neurotransmitter that plays a crucial role in nerve impulse transmission. It is a substrate for acetylcholinesterase, an enzyme that breaks down acetylcholine. Butyrylthiocholine is used as a substrate in the Ellman assay, a method for measuring acetylcholinesterase activity. The compound is also used in studies of cholinergic receptors and the mechanisms of cholinergic transmission. Butyrylthiocholine is synthesized by reacting butyryl chloride with thiocholine. It is a colorless, odorless solid that is soluble in water and ethanol. Butyrylthiocholine is a potent inhibitor of acetylcholinesterase and can cause cholinergic toxicity, characterized by symptoms such as muscle weakness, sweating, and respiratory distress. However, it is not used clinically due to its toxicity. Despite its toxicity, butyrylthiocholine plays a crucial role in research, specifically in understanding the mechanisms of cholinergic transmission and in the development of new drugs for the treatment of cholinergic diseases such as Alzheimer's disease.'

Butyrylthiocholine: A sulfur-containing analog of butyrylcholine which is hydrolyzed by butyrylcholinesterase to butyrate and thiocholine. It is used as a reagent in the determination of butyrylcholinesterase activity. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

butyrylthiocholine : A quaternary ammonium ion obtained by the formal condensation of the carboxy group of butyric acid with the thiol group of thiocholine. It is used as a reagent for determination of butyrylcholinesterase activity. [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 CID20689
CHEMBL ID139908
CHEMBL ID148530
CHEBI ID41055
SCHEMBL ID570209
MeSH IDM0003116

Synonyms (25)

Synonym
(propylcarbonylthioethyl)trimethylammonium iodide
2-(butyrylsulfanyl)-n,n,n-trimethylethanaminium
DB04250
butyrylthiocholine
ethanaminium, n,n,n-trimethyl-2-((1-oxobutyl)thio)-
2HA7 ,
4555-00-4
awbgqvbmgbzgls-uhfffaoysa-
inchi=1/c9h20nos/c1-5-6-9(11)12-8-7-10(2,3)4/h5-8h2,1-4h3/q+1
2-butanoylsulfanylethyl-trimethylazanium iodide
CHEMBL139908 ,
CHEMBL148530 ,
chebi:41055 ,
unii-k8d83ki04m
k8d83ki04m ,
SCHEMBL570209
bdbm8978
butanoylthiocholine
s-butyrylthiocholine
2-(butanoylsulfanyl)-n,n,n-trimethylethan-1-aminium
s-butanoylthiocholine
DTXSID00196553
2-(butanoylsulfanyl)-n,n,n-trimethylethanaminium
n,n,n-trimethyl-2-((1-oxobutyl)thio)ethanaminium
Q27095072

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"Individual plasma-converting enzyme activity was measured in 20 adult cancer patients participating in a pharmacokinetic and phase I clinical trial of a prolonged 96-h intravenous infusion of irinotecan."( Human plasma carboxylesterase and butyrylcholinesterase enzyme activity: correlations with SN-38 pharmacokinetics during a prolonged infusion of irinotecan.
Band, R; Bowen, D; Cottrell, J; Grem, JL; Guemei, AA; Hehman, H; Ismail, AS; Pavlov, MV; Prudhomme, M; Takimoto, CH; Taylor, RE, 2001
)
0.31
" Pharmacokinetic variations in the relative exposure to SN-38 did not correlate with the measured carboxylesterase-converting enzyme activity nor with plasma butyrylcholinesterase activity in our patient population."( Human plasma carboxylesterase and butyrylcholinesterase enzyme activity: correlations with SN-38 pharmacokinetics during a prolonged infusion of irinotecan.
Band, R; Bowen, D; Cottrell, J; Grem, JL; Guemei, AA; Hehman, H; Ismail, AS; Pavlov, MV; Prudhomme, M; Takimoto, CH; Taylor, RE, 2001
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
quaternary ammonium ionA derivative of ammonium, NH4(+), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups.
[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 (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)125.89300.00000.933210.0000AID32720
[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, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
Chain A, AcetylcholinesteraseMus musculus (house mouse)Kd440.000022.0000297.2000930.0000AID977611
[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 (3)

Assay IDTitleYearJournalArticle
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2006The Journal of biological chemistry, Sep-29, Volume: 281, Issue:39
Substrate and product trafficking through the active center gorge of acetylcholinesterase analyzed by crystallography and equilibrium binding.
AID1811Experimentally measured binding affinity data derived from PDB2006The Journal of biological chemistry, Sep-29, Volume: 281, Issue:39
Substrate and product trafficking through the active center gorge of acetylcholinesterase analyzed by crystallography and equilibrium binding.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (108)

TimeframeStudies, This Drug (%)All Drugs %
pre-199037 (34.26)18.7374
1990's27 (25.00)18.2507
2000's22 (20.37)29.6817
2010's21 (19.44)24.3611
2020's1 (0.93)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.70

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 Index27.70 (24.57)
Research Supply Index4.75 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index31.50 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.88%)5.53%
Reviews1 (0.88%)6.00%
Case Studies2 (1.75%)4.05%
Observational0 (0.00%)0.25%
Other110 (96.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]