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Edrophonium

July 24, 2017
Common Name

Edrophonium Description

Edrophonium is only found in individuals that have used or taken this drug. It is a rapid-onset, short-acting cholinesterase inhibitor used in cardiac arrhythmias and in the diagnosis of myasthenia gravis. It has also been used as an antidote to curare principles. [PubChem]Edrophonium works by prolonging the action acetylcholine, which is found naturally in the body. It does this by inhibiting the action of the enzyme acetylcholinesterase. Acetylcholine stimliates nicotinic and muscarinic receptors. When stimliated, these receptors have a range of effects. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (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 bromideMeSH Chloride, edrophoniumMeSH EdroponiumMeSH Bromide, edrophoniumMeSH TensilonMeSH

Chemical Formlia

C10H16NO Average Molecliar Weight

166.2401 Monoisotopic Molecliar 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

This compound belongs to the class of chemical entities known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Aniline and substituted anilines Alternative Parents

  • m-Aminophenols
  • 1-hydroxy-4-unsubstituted benzenoids
  • 1-hydroxy-2-unsubstituted benzenoids
  • Quaternary ammonium salts
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organic salts
  • Hydrocarbon derivatives
  • Amines
  • Organic cations

    • 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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

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

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antidotes
  • Cholinesterase Inhibitors

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Liquid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility4.86e-02 g/LNot Available LogP-2.95Not Available

    Predicted Properties

    Property Value Source Water Solubility0.049 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity62.41 m3·mol-1ChemAxon Polarizability19.15 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01010

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking 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 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB 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 NuGOwiki Link

    HMDB15145 Metagene Link

    HMDB15145 METLIN ID

    Not Available PubChem Compound

    3202 PDB ID

    EDR ChEBI ID

    251408

    Product: Oncrasin-2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not 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 ]

    PMID: 10636887

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