Ambenonium
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Ambenonium
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CAS No:
7648-98-8
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Formula:
C28H42Cl2N4O2
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Chemical Name:
Ambenonium
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Synonyms:
Benzenemethanaminium,N,N′-[(1,2-dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl)]bis[2-chloro-N,N-diethyl-;Ammonium,[oxalylbis(iminoethylene)]bis[(o-chlorobenzyl)diethyl-;N,N′-[(1,2-Dioxo-1,2-ethanediyl)bis(imino-2,1-ethanediyl)]bis[2-chloro-N,N-diethylbenzenemethanaminium];Ambenonium;[(2-Chlorophenyl)methyl](2-[[(2-[[(2-chlorophenyl)methyl]diethylazaniumyl]ethyl)carbamoyl]formamido]ethyl)diethylazanium
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CAS No:
Description
ChEBI: A symmetrical oxalamide-based bis-quaternary ammonium ion having ethyl and 2-chlorobenzyl groups attached to the nitrogens.
Solid
Ambenonium is a symmetrical oxalamide-based bis-quaternary ammonium ion having ethyl and 2-chlorobenzyl groups attached to the nitrogens. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor.|Ambenonium is a cholinesterase inhibitor. It is used in the management of myasthenia gravis.|Ambenonium is a Cholinesterase Inhibitor. The mechanism of action of ambenonium is as a Cholinesterase Inhibitor.|Ambenonium is a bisquaternary ammonium alcohol with parasympathomimetic activity. The positive charge of ambenonium allows it to act as an acetylcholinesterase inhibitor by binding to the anionic site at the reactive center of acetylcholinesterase, preventing the breakdown of acetylcholine and producing an indirect cholinomimetic effect at both nicotinic and muscarinic receptors. Ambenonium also has direct agonist activity at nicotinic receptors, potentiating the cholinomimetic effect at the neuromuscular junction.
Toxicity
LD50=150±44 mg/kg (orally in mice). 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.
Drug Information
Ambenonium is used to treat muscle weakness due to muscle disease (myasthenia gravis).
Ambenonium, similar to pyridostigmine and neostigmine, is used for the treatment of muscle weakness and fatigue in people with myasthenia gravis. It is postulated to exert its therapeutic effect by enhancing cholinergic function through the inhibition of the acetylcholine hydrolysis by acetylcholinesterase. Increased levels of acetylcholine has peripheral effects, as acetylcholine is also used in the brain, where it tends to cause excitatory actions. The glands that receive impulses from the parasympathetic part of the autonomic nervous system are also stimulated in the same way. This is why an increase in acetylcholine causes a decreased heart rate and increased production of saliva. Ambenonium is used less commonly than neostigmine or pyridostigmine but may be preferred in patients hypersensitive to the bromide ion. Ambenonium produces fewer muscarinic side effects than neostigmine, but more than pyridostigmine.
Oral - poorly absorbed from the gastrointestinal tract.
Plasma and hepatic
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 at the anionic site, which results in the blockage of the site of acetycholine binding, thereby inhibiting acetylcholine hydrolysis and enhancing cholinergic function through the accumulation of acetycholine at cholinergic synpases. Elevated acetylcholine levels lead to facilitates transmission of impulses across the myoneural junction.
Computed Properties
Molecular Weight:537.6
XLogP3:5.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:14
Exact Mass:536.2684820
Monoisotopic Mass:536.2684820
Topological Polar Surface Area:58.2
Heavy Atom Count:36
Formal Charge:2
Complexity:614
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes