Ambenonium (CED0015355)

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:25 UTC

Update Date

2026-05-14 16:58:01 UTC

SynCED ID

CED0015355

Secondary Accession Numbers

CHEM002352
T3D2991

Identification

Common Name

Ambenonium

Class

Small Molecule

Description

Ambenonium is an exogenous solid with the chemical formula C28H42Cl2N4O2. Ambenonium belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 537.57 g/mol, Ambenonium is a heavy molecule. It is recorded as being found in healthcare, pharmaceuticals and veterinary products as a parasympathomimetic, as well as in hybrid capacitors within electrical and electronic equipment. The recorded route of exposure for this compound is oral. Ambenonium functions as a biological and chemical inhibitor of cholinesterase (EC 3.1.1.8). Its primary protein target is acetylcholinesterase. Ambenonium exerts its actions against myasthenia gravis by competitive, reversible inhibition of acetylcholinesterase. Myasthenia gravis occurs when the body inappropriately produces antibodies against acetylcholine receptors, inhibiting proper acetylcholine signal transmission. Ambenonium reversibly binds acetylcholinesterase, which helps manage the condition.

Contaminant Type

Amide
Amine
Anti-Arrhythmia Agent
Antimyasthenic Agent
Drug
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ambenonium base	ChEBI
Ambenonum	ChEBI
Mytelase	HMDB
Ambenonium chloride	HMDB
Chloride, ambenonium	HMDB
Sanofi winthrop brand OF ambenonium chloride	HMDB

Chemical Formula

C₂₈H₄₂Cl₂N₄O₂

Average Molecular Mass

537.565 g/mol

Monoisotopic Mass

536.268 g/mol

CAS Registry Number

7648-98-8

IUPAC Name

[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium

Traditional Name

ambenonium

SMILES

CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C28H40Cl2N4O2/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30/h9-16H,5-8,17-22H2,1-4H3/p+2

InChI Key

OMHBPUNFVFNHJK-UHFFFAOYSA-P

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Benzylamine
Phenylmethylamine
Aralkylamine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organic salt
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:2627 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

EC 3.1.1.8 (cholinesterase) inhibitor ?An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).

Chemical Roles

EC 3.1.1.8 (cholinesterase) inhibitor ?

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	196-199°C
Boiling Point	Not Available
Solubility	Soluble

Predicted Properties

Property	Value	Source
Water Solubility	9.4e-07 g/L	ALOGPS
logP	2.27	ALOGPS
logP	-3.6	ChemAxon
logS	-8.8	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	173.57 m³·mol⁻¹	ChemAxon
Polarizability	59.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
48.0 Log mg/kg [30:86]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Ambenonium is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. LD₅₀=150±44 mg/kg (orally in mice).

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Symptoms of overdose include muscle twitching, weakness and paralysis of voluntary muscles including the tongue, shoulders, neck and arms, blood pressure increase (with or without a slowing of heart rate), a sensation of internal trembling, severe anxiety, and panic. Death may occur rapidly if untreated.

Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000381	Parasympathomimetics?Parasympathomimetics are synthetic chemicals that mimic the action of the neurotransmitter acetylcholine, stimulating the parasympathetic nervous system.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000524	Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.	Electrical & Electronic Equipment	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Ambenonium Action Pathway (new)

Ambenonium Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	1-deoxy-D-xylulose-5-phosphate synthase	Q4QKG6	Haemophilus influenzae (strain 86-028NP)	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.34 Statistical Significance 6.00e-05 Supporting Reference Compounds 2 E-value 0.467095
Click to view 3D structure	Phospholipase A and acyltransferase 4	Q9UL19	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.314 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 12.923
Click to view 3D structure	Phospholipase A and acyltransferase 5	Q96KN8	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.314 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 12.923
Click to view 3D structure	Phospholipase A and acyltransferase 3	P53816	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.314 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 12.923
Click to view 3D structure	Phospholipase A and acyltransferase 2	Q9NWW9	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.314 Statistical Significance 0.0017 Supporting Reference Compounds 1 E-value 12.923
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.327 Statistical Significance 0.0193 Supporting Reference Compounds 201 E-value 150.171
Click to view 3D structure	Chloride intracellular channel protein 1	O00299	Humans	Predicted (SEA)	Prediction Confidence Score 0.291 Applicability Domain 0.291 Low confidence Statistical Significance 4.40e-04 Supporting Reference Compounds 1 E-value 3.42537
Click to view 3D structure	1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic	Q38854	Arabidopsis thaliana	Predicted (SEA)	Prediction Confidence Score 0.288 Applicability Domain 0.288 Low confidence Statistical Significance 2.40e-04 Supporting Reference Compounds 1 E-value 1.86838
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	Prediction Confidence Score 0.282 Applicability Domain 0.327 Statistical Significance 0.0122 Supporting Reference Compounds 106 E-value 94.6646
Click to view 3D structure	Protein arginine N-methyltransferase 1	Q63009	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.281 Applicability Domain 0.296 Low confidence Statistical Significance 2.30e-04 Supporting Reference Compounds 3 E-value 1.79053
Click to view 3D structure	Chaperone protein dnaK	C3TRK2	Escherichia coli	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.278 Low confidence Statistical Significance 0.0022 Supporting Reference Compounds 1 E-value 17.4382
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.292 Low confidence Statistical Significance 0.0926 Supporting Reference Compounds 407 E-value 720.962
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.292 Low confidence Statistical Significance 0.1204 Supporting Reference Compounds 472 E-value 937.305
Click to view 3D structure	Interleukin-8	P10145	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.327 Statistical Significance 0.0024 Supporting Reference Compounds 26 E-value 19.0731
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.327 Statistical Significance 0.0347 Supporting Reference Compounds 136 E-value 269.825
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	Prediction Confidence Score 0.262 Applicability Domain 0.333 Statistical Significance 0.0873 Supporting Reference Compounds 425 E-value 679.779
Click to view 3D structure	Transthyretin	P02766	Humans	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.327 Statistical Significance 0.0099 Supporting Reference Compounds 55 E-value 77.46
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.283 Low confidence Statistical Significance 0.3876 Supporting Reference Compounds 1245 E-value 3017.83
Click to view 3D structure	Protein RecA	P9WHJ3	Mycobacterium tuberculosis	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.278 Low confidence Statistical Significance 0.0659 Supporting Reference Compounds 296 E-value 513.182
Click to view 3D structure	Prostaglandin G/H synthase 2	Q05769	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.327 Statistical Significance 0.0093 Supporting Reference Compounds 43 E-value 72.789
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.257 Applicability Domain 0.297 Low confidence Statistical Significance 0.2872 Supporting Reference Compounds 793 E-value 2236.22
Click to view 3D structure	GABA transporter 2	P31651	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.288 Low confidence Statistical Significance 0.002 Supporting Reference Compounds 13 E-value 15.8812
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.288 Low confidence Statistical Significance 0.2768 Supporting Reference Compounds 763 E-value 2154.79
Click to view 3D structure	DNA damage-inducible transcript 3 protein	P35639	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.292 Low confidence Statistical Significance 0.0639 Supporting Reference Compounds 226 E-value 497.379
Click to view 3D structure	X-box-binding protein 1	P17861	Humans	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.292 Low confidence Statistical Significance 0.0639 Supporting Reference Compounds 227 E-value 497.534
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Known	Ambenonium exerts its actions against myasthenia gravis by competitive, reversible inhibition of acetylcholinesterase. The disease myasthenia gravis occurs when the body inappropriately produces antibodies against acetylcholine receptors, and thus inhibits proper acetylcholine signal transmission (when acetylcholine binds to acetylcholine receptors of striated muscle fibers, it stimulates those fibers to contract). Ambenonium reversibly binds acetylcholinesterase, and as acetylcholinesterase is responsible for the hydrolysis of acetylcholine, this inhibition increases levels of acetylcholine. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.