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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015145

Secondary Accession Numbers

HMDB15145

Metabolite Identification

Common Name

Edrophonium

Description

Edrophonium, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1010                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -2.988   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   1.632   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       5.748   3.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.748   0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.288   1.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   1.632   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   3.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.988   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    3    4    5    6                                             
CONECT    3    2    7                                                       
CONECT    4    2    8    9                                                  
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    4   10                                                       
CONECT    9    4   11                                                       
CONECT   10    1    8   12                                                  
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0015145
HETATM    1  C1  UNL     1      -1.869   1.784   0.542  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.801   0.305   0.718  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.972  -0.364  -0.261  1.00  0.00           N1+
HETATM    4  C3  UNL     1      -1.358  -1.782  -0.219  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.276   0.128  -1.580  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.398  -0.296   0.035  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.845  -0.781   1.252  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.180  -0.742   1.600  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.078  -0.204   0.703  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.687   0.296  -0.528  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.605   0.839  -1.428  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.342   0.231  -0.821  1.00  0.00           C  
HETATM   13  H1  UNL     1      -2.885   2.053   0.137  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.055   2.224  -0.035  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.812   2.239   1.573  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.453  -0.007   1.728  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.828  -0.152   0.618  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.348  -2.224  -1.232  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.673  -2.300   0.481  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.385  -1.889   0.203  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.954   1.148  -1.766  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.368   0.068  -1.746  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.747  -0.560  -2.300  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.171  -1.213   1.987  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.518  -1.123   2.551  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.152  -0.148   0.930  1.00  0.00           H  
HETATM   27  H15 UNL     1       3.780   1.842  -1.345  1.00  0.00           H  
HETATM   28  H16 UNL     1       1.027   0.627  -1.798  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    5    6
CONECT    4   18   19   20
CONECT    5   21   22   23
CONECT    6    7    7   12
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3-Hydroxyphenyl)dimethylethylammonium	ChEBI
3-Hydroxy-N,N-dimethyl-N-ethylanilinium	ChEBI
EDROPHONIUM ion	ChEBI
Ethyl-(3-hydroxy-phenyl)-dimethyl-ammonium	ChEBI
N-Ethyl-3-hydroxy-N,N-dimethylbenzenaminium	ChEBI
EDR	HMDB
Edrophone chloride	HMDB
Edrophonium chloride	HMDB
Edrophonum	HMDB
Edrophonium bromide	HMDB
Chloride, edrophonium	HMDB
Edroponium	HMDB
Bromide, edrophonium	HMDB
Tensilon	HMDB

Chemical Formula

C₁₀H₁₆NO

Average Molecular Weight

166.2401

Monoisotopic Molecular Weight

166.123189139

IUPAC Name

N-ethyl-3-hydroxy-N,N-dimethylanilinium

Traditional Name

tensilon

CAS Registry Number

116-38-1

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 Key

VWLHWLSRQJQWRG-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:251408 )
quaternary ammonium ion (CHEBI:251408 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015145)

Source

Exogenous

Exogenous (HMDB: HMDB0015145)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.049 g/L	Not Available
LogP	-2.95	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.41 m³·mol⁻¹	ChemAxon
Polarizability	19.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.395	31661259
DarkChem	[M-H]-	134.779	31661259
DeepCCS	[M+H]+	132.992	30932474
DeepCCS	[M-H]-	130.596	30932474
DeepCCS	[M-2H]-	165.449	30932474
DeepCCS	[M+Na]+	139.909	30932474
AllCCS	[M+H]+	134.7	32859911
AllCCS	[M+H-H2O]+	130.5	32859911
AllCCS	[M+NH4]+	138.6	32859911
AllCCS	[M+Na]+	139.8	32859911
AllCCS	[M-H]-	148.1	32859911
AllCCS	[M+Na-2H]-	149.4	32859911
AllCCS	[M+HCOO]-	150.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Edrophonium	CC[N+](C)(C)C1=CC(O)=CC=C1	2283.3	Standard polar	33892256
Edrophonium	CC[N+](C)(C)C1=CC(O)=CC=C1	1290.7	Standard non polar	33892256
Edrophonium	CC[N+](C)(C)C1=CC(O)=CC=C1	1462.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Edrophonium,1TMS,isomer #1	CC[N+](C)(C)C1=CC=CC(O[Si](C)(C)C)=C1	1464.0	Semi standard non polar	33892256
Edrophonium,1TBDMS,isomer #1	CC[N+](C)(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	1685.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Edrophonium GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-416237a97b8a91587c90	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Edrophonium GC-MS (1 TMS) - 70eV, Positive	splash10-05g3-7980000000-a7701077cc6ccdafb9fd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Edrophonium GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Edrophonium 10V, Positive-QTOF	splash10-014i-0900000000-8881fed25764397ebd5c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Edrophonium 20V, Positive-QTOF	splash10-014r-0900000000-023a5d3362134235aff3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Edrophonium 40V, Positive-QTOF	splash10-00ds-9400000000-feb5088a9c0f0f47c123	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01010	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01010	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01010

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3090

KEGG Compound ID

C06976

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Edrophonium

METLIN ID

Not Available

PubChem Compound

3202

PDB ID

EDR

ChEBI ID

251408

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Acetylcholinesterase

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

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 ]
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 ]
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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]

Enzyme Details

2. Cholinesterase

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

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 ]
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 ]

Showing metabocard for Edrophonium (HMDB0015145)

MOL for HMDB0015145 (Edrophonium)

3D MOL for HMDB0015145 (Edrophonium)

3D SDF for HMDB0015145 (Edrophonium)

3D-SDF for HMDB0015145 (Edrophonium)

PDB for HMDB0015145 (Edrophonium)

3D PDB for HMDB0015145 (Edrophonium)

SMILES for HMDB0015145 (Edrophonium)

INCHI for HMDB0015145 (Edrophonium)

Structure for HMDB0015145 (Edrophonium)

3D Structure for HMDB0015145 (Edrophonium)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References