Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015145
Secondary Accession Numbers
  • HMDB15145
Metabolite Identification
Common NameEdrophonium
DescriptionEdrophonium, also known as tensilon, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Edrophonium is a drug which is used for the differential diagnosis of myasthenia gravis and as an adjunct in the evaluation of treatment requirements in this disease. it may also be used for evaluating emergency treatment in myasthenic crises. Edrophonium is an extremely weak basic (essentially neutral) compound (based on its pKa). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group.
Structure
Data?1582753263
Synonyms
ValueSource
(3-Hydroxyphenyl)dimethylethylammoniumChEBI
3-Hydroxy-N,N-dimethyl-N-ethylaniliniumChEBI
EDROPHONIUM ionChEBI
Ethyl-(3-hydroxy-phenyl)-dimethyl-ammoniumChEBI
N-Ethyl-3-hydroxy-N,N-dimethylbenzenaminiumChEBI
EDRHMDB
Edrophone chlorideHMDB
Edrophonium chlorideHMDB
EdrophonumHMDB
Edrophonium bromideHMDB
Chloride, edrophoniumHMDB
EdroponiumHMDB
Bromide, edrophoniumHMDB
TensilonHMDB
Chemical FormulaC10H16NO
Average Molecular Weight166.2401
Monoisotopic Molecular Weight166.123189139
IUPAC NameN-ethyl-3-hydroxy-N,N-dimethylanilinium
Traditional Nametensilon
CAS Registry Number116-38-1
SMILES
CC[N+](C)(C)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1
InChI KeyVWLHWLSRQJQWRG-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAniline and substituted anilines
Direct ParentAniline and substituted anilines
Alternative Parents
Substituents
  • Aminophenol
  • M-aminophenol
  • Aniline or substituted anilines
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Quaternary ammonium salt
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.049 g/LNot Available
LogP-2.95Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP-1.6ALOGPS
logP-1.9ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.59ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.41 m³·mol⁻¹ChemAxon
Polarizability19.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.39531661259
DarkChem[M-H]-134.77931661259
DeepCCS[M+H]+132.99230932474
DeepCCS[M-H]-130.59630932474
DeepCCS[M-2H]-165.44930932474
DeepCCS[M+Na]+139.90930932474
AllCCS[M+H]+134.732859911
AllCCS[M+H-H2O]+130.532859911
AllCCS[M+NH4]+138.632859911
AllCCS[M+Na]+139.832859911
AllCCS[M-H]-148.132859911
AllCCS[M+Na-2H]-149.432859911
AllCCS[M+HCOO]-150.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EdrophoniumCC[N+](C)(C)C1=CC(O)=CC=C12283.3Standard polar33892256
EdrophoniumCC[N+](C)(C)C1=CC(O)=CC=C11290.7Standard non polar33892256
EdrophoniumCC[N+](C)(C)C1=CC(O)=CC=C11462.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Edrophonium,1TMS,isomer #1CC[N+](C)(C)C1=CC=CC(O[Si](C)(C)C)=C11464.0Semi standard non polar33892256
Edrophonium,1TBDMS,isomer #1CC[N+](C)(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C11685.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Edrophonium GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-416237a97b8a91587c902017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Edrophonium GC-MS (1 TMS) - 70eV, Positivesplash10-05g3-7980000000-a7701077cc6ccdafb9fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Edrophonium GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edrophonium 10V, Positive-QTOFsplash10-014i-0900000000-8881fed25764397ebd5c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edrophonium 20V, Positive-QTOFsplash10-014r-0900000000-023a5d3362134235aff32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Edrophonium 40V, Positive-QTOFsplash10-00ds-9400000000-feb5088a9c0f0f47c1232017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H 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 DB01010 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01010 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01010
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3090
KEGG Compound IDC06976
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEdrophonium
METLIN IDNot Available
PubChem Compound3202
PDB IDEDR
ChEBI ID251408
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. Ravelli RB, Raves ML, Ren Z, Bourgeois D, Roth M, Kroon J, Silman I, Sussman JL: Static Laue diffraction studies on acetylcholinesterase. Acta Crystallogr D Biol Crystallogr. 1998 Nov 1;54(Pt 6 Pt 2):1359-66. [PubMed:10089512 ]
  2. Keymer JE, Gaete J, Kameid G, Alvarez J: Acetylcholinesterase and inhibitors: effects upon normal and regenerating nerves of the rat. Eur J Neurosci. 1999 Mar;11(3):1049-57. [PubMed:10103097 ]
  3. Huby F, Mallet S, Hoste H: Role of acetylcholinesterase (AChE) secreted by parasitic nematodes on the growth of the cell line from epithelial origin HT29-D4. Parasitology. 1999 May;118 ( Pt 5):489-98. [PubMed:10363282 ]
  4. Luo C, Saxena A, Ashani Y, Leader H, Radic Z, Taylor P, Doctor BP: Role of edrophonium in prevention of the re-inhibition of acetylcholinesterase by phosphorylated oxime. Chem Biol Interact. 1999 May 14;119-120:129-35. [PubMed:10421446 ]
  5. Luo C, Saxena A, Smith M, Garcia G, Radic Z, Taylor P, Doctor BP: Phosphoryl oxime inhibition of acetylcholinesterase during oxime reactivation is prevented by edrophonium. Biochemistry. 1999 Aug 3;38(31):9937-47. [PubMed:10433700 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Martin-Biosca Y, Asensi-Bernardi L, Villanueva-Camanas RM, Sagrado S, Medina-Hernandez MJ: Screening of acetylcholinesterase inhibitors by CE after enzymatic reaction at capillary inlet. J Sep Sci. 2009 May;32(10):1748-56. doi: 10.1002/jssc.200800701. [PubMed:19472276 ]
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. Harel M, Sussman JL, Krejci E, Bon S, Chanal P, Massoulie J, Silman I: Conversion of acetylcholinesterase to butyrylcholinesterase: modeling and mutagenesis. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10827-31. [PubMed:1438284 ]
  2. Saxena A, Redman AM, Jiang X, Lockridge O, Doctor BP: Differences in active site gorge dimensions of cholinesterases revealed by binding of inhibitors to human butyrylcholinesterase. Biochemistry. 1997 Dec 2;36(48):14642-51. [PubMed:9398183 ]