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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:16 UTC
HMDB IDHMDB0015254
Secondary Accession Numbers
  • HMDB15254
Metabolite Identification
Common NameAmbenonium
DescriptionAmbenonium is only found in individuals that have used or taken this drug. It is a cholinesterase inhibitor used in the management of myasthenia gravis. [Wikipedia ]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. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.
Structure
Data?1582753276
Synonyms
ValueSource
Ambenonium baseChEBI
AmbenonumChEBI
MytelaseHMDB
Ambenonium chlorideHMDB
Chloride, ambenoniumHMDB
Sanofi winthrop brand OF ambenonium chlorideHMDB
Chemical FormulaC28H42Cl2N4O2
Average Molecular Weight537.565
Monoisotopic Molecular Weight536.268482022
IUPAC Name[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium
Traditional Nameambenonium
CAS Registry Number7648-98-8
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 KeyOMHBPUNFVFNHJK-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point196 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.4e-07 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.4e-07 g/LALOGPS
logP10(2.27) g/LALOGPS
logP10(-3.6) g/LChemAxon
logS10(-8.8) g/LALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity173.57 m³·mol⁻¹ChemAxon
Polarizability59.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+209.16530932474
DeepCCS[M-H]-206.80730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmbenoniumCC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl4849.3Standard polar33892256
AmbenoniumCC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl2564.6Standard non polar33892256
AmbenoniumCC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl3991.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ambenonium,1TMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl3922.2Semi standard non polar33892256
Ambenonium,1TMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl3896.5Standard non polar33892256
Ambenonium,1TMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl4974.6Standard polar33892256
Ambenonium,2TMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl3898.8Semi standard non polar33892256
Ambenonium,2TMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl3913.1Standard non polar33892256
Ambenonium,2TMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl4640.4Standard polar33892256
Ambenonium,1TBDMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4110.3Semi standard non polar33892256
Ambenonium,1TBDMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4100.9Standard non polar33892256
Ambenonium,1TBDMS,isomer #1CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4954.0Standard polar33892256
Ambenonium,2TBDMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4268.5Semi standard non polar33892256
Ambenonium,2TBDMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4268.2Standard non polar33892256
Ambenonium,2TBDMS,isomer #1CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl4621.4Standard polar33892256
Spectra

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01122 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01122 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01122
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2046
KEGG Compound IDC07773
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmbenonium
METLIN IDNot Available
PubChem Compound2131
PDB IDNot Available
ChEBI ID2627
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  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:11330337 ]
  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:1588924 ]
  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:15982786 ]
  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:2857786 ]
  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:5833399 ]
  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:13679187 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  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:1801966 ]