Page last updated: 2024-12-05

ambenonium chloride

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

Description

Ambenonium Chloride: A quaternary ammonium compound that is an inhibitor of cholinesterase activity with actions similar to those of NEOSTIGMINE, but of longer duration. Ambenonium is given by mouth in the treatment of myasthenia gravis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1112) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ambenonium chloride : A symmetrical oxalamide-based bis-quaternary ammonium salt having ethyl and 2-chlorobenzyl groups attached to the nitrogens. [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 CID8288
CHEMBL ID1200541
CHEBI ID2628
SCHEMBL ID133487
MeSH IDM0000853

Synonyms (79)

Synonym
(oxalylbis(iminoethylen))bis(2-chlorbenzyl)diethylammonium chlorid)
einecs 204-107-5
ambestigmin chloride
oxazil
chlorure d'ambenonium [inn-french]
ambenonii chloridum [inn-latin]
win 8077
ambenonium dichloride
oxamizil
ammonium, (oxalylbis(iminoethylene))bis((o-chlorobenzyl)diethyl-, dichloride
benzenemethanaminium, n,n'-((1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl))bis(2-chloro-n,n-diethyl-, dichloride
n,n'-bis(2-diethylaminoethyl)oxamide bis(2-chlorobenzyl chloride)
ambenonii chloridum
misuran
benzenemethanaminium, n,n'-((1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl))bis(2-chloro-n,n-diethyl)-, dichloride
oksazil
n,n'-bis(2-diethylaminoethyl)oxamid bis-2-chlorbenzyl chlorid
oxazylum
cloruro de ambenonio [inn-spanish]
mytelase
oxazyl
ai3-22370
(oxalylbis(iminoethylene))bis((o-chlorobenzyl)diethylammonium) dichloride
mysuran
HMS3266K15
ambenonium chloride
2,2'-[(1,2-dioxoethane-1,2-diyl)diimino]bis{n-[(2-chlorophenyl)methyl]-n,n-diethylethanaminium} dichloride
115-79-7
mytelase (tn)
ambenonium chloride (jp17/inn)
D01001
chloride, ambenonium
CHEMBL1200541 ,
chlorure d'ambenonium
cloruro de ambenonio
2,2'-[(1,2-dioxoethane-1,2-diyl)diimino]bis[n-(2-chlorobenzyl)-n,n-diethylethanaminium] dichloride
CHEBI:2628 ,
dtxcid402582
cas-115-79-7
tox21_112030
dtxsid3022582 ,
unii-51fob87g3i
ambenonium chloride [usp:inn:ban:jan]
51fob87g3i ,
ambenonium chloride [who-dd]
ambenonium chloride [orange book]
ambenonium chloride [jan]
[oxalylbis(iminoethylene)]bis[(o-chlorobenzyl)diethylammonium] dichloride
ambenonium chloride [vandf]
ambenonium chloride [mi]
ambenonium chloride [inn]
SCHEMBL133487
tox21_112030_1
NCGC00024567-03
n,n'-[(1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl)]bis(2-chloro-n,n-diethylbenzenemethaminium) dichloride
AKOS024457845
sr-01000597958
SR-01000597958-1
HY-100919
ambenonium (chloride)
n,n'-oxalylbis(n-2-aminoethyl-n-2-chlorobenzyldiethylammonium) dichloride
HMS3678F07
Q27105751
HMS3414F07
(2-chlorophenyl)methyl-[2-[[2-[2-[(2-chlorophenyl)methyl-diethylazaniumyl]ethylamino]-2-oxoacetyl]amino]ethyl]-diethylazanium;dichloride
n,n'-[(1,2-dioxo-1,2-ethanediyl)bis( imino-2,1-ethanediyl)]bis(2-chloro-n,n-diethylbenz enemethaminium) dichloride
CS-0020589
cloruro de ambenonio (inn-spanish)
2,2'-((1,2-dioxoethane-1,2-diyl)diimino)bis(n-(2-chlorobenzyl)-n,n-diethylethanaminium) dichloride
ambenonium chloride (usp:inn:ban:jan)
(oxalylbis(iminoethylene))bis((o-chlorobenzyl)diethyl-ammonium), dichloride
ambenonii chloridum (inn-latin)
n,n'-((1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl))bis(2-chloro-n,n-diethyl-benzenemethanaminium), dichloride
ambanonium (cation)
chlorure d'ambenonium (inn-french)
n07aa30
2,2'-((1,2-dioxoethane-1,2-diyl)diimino)bis(n-(2-chlorobenzyl)-n,n-diethylethylaminium) dichloride
[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium dichloride
EN300-19741614

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" A pharmacodynamic model was developed by considering acetylcholinesterase (AChE) inhibition, direct antagonism to the nicotinic receptor, and desensitization of the nicotinic receptor."( Pharmacodynamic analysis of contractile potentiation by cholinesterase inhibitors in rats.
Iga, T; Sawada, Y; Yamamoto, K, 1996
)
0.29

Bioavailability

ExcerptReferenceRelevance
" These characteristic properties of ambenonium chloride could explain the erratic pattern of bioavailability observed as well as the difficulty in controlling the disease in some patients."( Pharmacokinetic studies of ambenonium chloride in patients with myasthenia gravis.
Boucly, P; Boucly-Goester, C; Chabenat, C; Elkharrat, D; Gajdos, P; Marchand, J; Tharasse-Bloch, C,
)
0.7
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Patients must be advised to keep to the dosing and dietary schedule in order to avoid unexpected adverse actions to AMBC."( Influence of food on serum ambenonium concentration in patients with myasthenia gravis.
Aoyama, T; Fujii, N; Goto, I; Higuchi, S; Ohtsubo, K; Tatsuhara, T, 1992
)
0.28
"Ambenonium chloride was administered orally in a dosage of 6 mg/kg/day to rats for 14-360 days."( Effects of long-term administration of ambenonium chloride on motor end-plate fine structure and acetylcholine receptor in rat.
Hazama, R; Mori, K; Mori, M; Shibuya, N; Takamori, M; Tsujihata, M, 1981
)
1.97
" administration decreased at high doses of each drug and the dose-response curves were biphasic."( Pharmacodynamic analysis of contractile potentiation by cholinesterase inhibitors in rats.
Iga, T; Sawada, Y; Yamamoto, K, 1996
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

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).
neurotransmitter agentA substance used for its pharmacological action on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function.
[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 (2)

ClassDescription
quaternary ammonium saltDerivatives of ammonium compounds, (NH4(+))Y(-), in which all four of the hydrogens bonded to nitrogen have been replaced with univalent (usually organyl) groups.
organic chloride 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 (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency19.40920.002541.796015,848.9004AID1347395; AID1347397; AID1347398; AID1347399
cytochrome P450 family 3 subfamily A polypeptide 4Homo sapiens (human)Potency7.76190.01237.983543.2770AID1645841
cytochrome P450 2D6Homo sapiens (human)Potency15.48710.00108.379861.1304AID1645840
activating transcription factor 6Homo sapiens (human)Potency0.11990.143427.612159.8106AID1159516
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (119)

TimeframeStudies, This Drug (%)All Drugs %
pre-199083 (69.75)18.7374
1990's10 (8.40)18.2507
2000's10 (8.40)29.6817
2010's10 (8.40)24.3611
2020's6 (5.04)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.26

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 Index29.26 (24.57)
Research Supply Index4.91 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (2.24%)6.00%
Case Studies12 (8.96%)4.05%
Observational0 (0.00%)0.25%
Other119 (88.81%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]