You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Accession NumberDB01122  (APRD00771)
TypeSmall Molecule

Ambenonium is a cholinesterase inhibitor used in the management of myasthenia gravis. [Wikipedia]

AmbenoniumNot AvailableNot Available
Ambenonium baseNot AvailableNot Available
AmbenonumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
MysuranNot Available
MytelaseNot Available
Brand mixturesNot Available
SaltsNot Available
CAS number7648-98-8
WeightAverage: 537.565
Monoisotopic: 536.268482022
Chemical FormulaC28H42Cl2N4O2
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
  • Alpha-amino acid amide
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Quaternary ammonium salt
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
IndicationAmbenonium is used to treat muscle weakness due to muscle disease (myasthenia gravis).
PharmacodynamicsAmbenonium, 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.
Mechanism of actionAmbenonium 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. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.
AbsorptionOral - poorly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available

Plasma and hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption-0.9618
Blood Brain Barrier+0.8373
Caco-2 permeable+0.5168
P-glycoprotein substrateSubstrate0.8725
P-glycoprotein inhibitor INon-inhibitor0.6717
P-glycoprotein inhibitor IINon-inhibitor0.766
Renal organic cation transporterNon-inhibitor0.823
CYP450 2C9 substrateNon-substrate0.7865
CYP450 2D6 substrateNon-substrate0.7008
CYP450 3A4 substrateSubstrate0.5842
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateNon-inhibitor0.6899
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.538
Ames testNon AMES toxic0.7312
BiodegradationNot ready biodegradable0.9927
Rat acute toxicity2.4379 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9665
hERG inhibition (predictor II)Inhibitor0.8507
ManufacturersNot Available
Dosage formsNot Available
Unit descriptionCostUnit
Mytelase 10 mg caplet1.86USD caplet
Mytelase 10 mg tablet1.86USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Experimental Properties
melting point196-199 °CKirchner, F.K.; U.S. Patent 3,096,373; July 2,1963; assigned to Sterling Drug Inc.
water solubilitySolubleNot Available
Predicted Properties
Water Solubility9.42e-07 mg/mLALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity173.57 m3·mol-1ChemAxon
Polarizability59.98 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Kirchner, F.K.; U.S. Patent 3,096,373; July 2,1963; assigned to Sterling Drug Inc.

General ReferenceNot Available
External Links
ATC CodesN07AA30
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (166 KB)
Drug InteractionsNot Available
Food InteractionsNot Available


1. Acetylcholinesterase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor


Name UniProt ID Details
Acetylcholinesterase P22303 Details


  1. Lockhart B, Closier M, Howard K, Steward C, Lestage P: Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. Naunyn Schmiedebergs Arch Pharmacol. 2001 Apr;363(4):429-38. Pubmed
  2. Hodge AS, Humphrey DR, Rosenberry TL: Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities. Mol Pharmacol. 1992 May;41(5):937-42. Pubmed
  3. Papp MI, Komoly S, Szirmai IG, Kovacs T: Similarities between CSF-brain extracellular transfer and neurofibrillary tangle invasion in Alzheimer’s disease. Neurobiol Aging. 2006 Mar;27(3):402-12. Epub 2005 Jun 27. Pubmed
  4. Kenakin TP, Beek D: Self-cancellation of drug properties as a mode of organ selectivity: the antimuscarinic effects of ambenonium. J Pharmacol Exp Ther. 1985 Mar;232(3):732-40. Pubmed
  5. Webb GD: Affinity of benzoquinonium and ambenonium derivatives for the acetylcholine receptor, tested on the electroplax, and for acetylcholinesterase in solution. Biochim Biophys Acta. 1965 May 25;102(1):172-84. Pubmed
  6. Bolognesi ML, Cavalli A, Andrisano V, Bartolini M, Banzi R, Antonello A, Rosini M, Melchiorre C: Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors. Farmaco. 2003 Sep;58(9):917-28. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed


1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown


Name UniProt ID Details
Cholinesterase P06276 Details


  1. Yamamoto K, Kohda Y, Sawada Y, Iga T: Pharmacokinetics of ambenonium, a reversible cholinesterase inhibitor, in rats. Biopharm Drug Dispos. 1991 Nov;12(8):613-25. Pubmed

comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on March 27, 2014 13:54