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Identification
NameEdrophonium
Accession NumberDB01010  (APRD00944)
TypeSmall Molecule
GroupsApproved
Description

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]

Structure
Thumb
Synonyms
(3-Hydroxyphenyl)dimethylethylammonium
3-hydroxy-N,N-dimethyl-N-ethylanilinium
EDR
Edrophonium
Edrophonium Ion
Ethyl-(3-hydroxy-phenyl)-dimethyl-ammonium
N-ethyl-3-hydroxy-N,N-dimethylanilinium
N-ethyl-3-hydroxy-N,N-dimethylbenzenaminium
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Enlon 10mg/mlliquid10 mgintravenousBaxter Corporation1996-09-182008-01-28Canada
Enlon Liq IV 10mg/mlliquid10 mgintravenousOhmeda Pharmaceutical Products, Division Of Boc Canada Limited1995-12-311996-09-26Canada
Tensilonliquid10 mgintramuscular; intravenousValeant Canada Lp/valeant Canada s.e.c.1988-12-312016-07-08Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Enloninjection, solution10 mg/mLintramuscular; intravenousMylan Institutional LLC2013-04-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AntirexKyorin
ReversolNot Available
Brand mixtures
NameLabellerIngredients
Enlon PlusMylan Institutional LLC
Salts
Name/CASStructureProperties
Edrophonium Chloride
116-38-1
Thumb
  • InChI Key: BXKDSDJJOVIHMX-UHFFFAOYSA-N
  • Monoisotopic Mass: 201.092041846
  • Average Mass: 201.693
DBSALT000475
Categories
UNII70FP3JLY7N
CAS numberNot Available
WeightAverage: 166.2401
Monoisotopic: 166.123189139
Chemical FormulaC10H16NO
InChI KeyInChIKey=VWLHWLSRQJQWRG-UHFFFAOYSA-O
InChI
InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1
IUPAC Name
N-ethyl-3-hydroxy-N,N-dimethylanilinium
SMILES
CC[N+](C)(C)C1=CC(O)=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminophenols. These are organic compounds containing an amino group attached to a phenol.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentAminophenols
Alternative Parents
Substituents
  • Substituted aniline
  • Aminophenol
  • Aniline
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsEdrophonium is a short and rapid-acting anticholinesterase drug. Its effect is manifest within 30 to 60 seconds after injection and lasts an average of 10 minutes. Edrophonium's pharmacologic action is due primarily to the inhibition or inactivation of acetylcholinesterase at sites of cholinergic transmission. Nicotinic acetylcholine (nAChR)receptors are found throughout the body, especially on muscle. Stimulation of these receptors causes to muscle contraction. In myasthenia gravis the body's immune system destroys many of the nicotinic acetylcholine receptors, so that the muscle becomes less responsive to nervous stimulation. Edrophonium chloride increases the amount of acetylcholine at the nerve endings. Increased levels of acetylcholine allow the remaining receptors to function more efficiently.
Mechanism of actionEdrophonium 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 stimulates nicotinic and muscarinic receptors. When stimulated, these receptors have a range of effects.
Related Articles
AbsorptionRapidly absorbed.
Volume of distribution
  • 1.6±0.4 L/kg [Adults]
  • 2.2±1.5 L/kg [Children (0.08-10 yrs)]
  • 1.8±1.2 L/kg [Elderly (65-75 yrs)]
Protein bindingNot Available
MetabolismNot Available
Route of eliminationEdrophonium is primarily renally excreted with 67% of the dose appearing in the urine. Hepatic metabolism and biliary excretion have also been demonstrated in animals
Half lifeDistribution half-life is 7 to 12 minutes. Elimination half-life is 33 to 110 minutes.
Clearance
  • 6.8 +/- 2. mL/kg/min [Adults]
  • 6.4 +/- 3.9 mL/kg/min [Children (0.08-10 yrs)]
  • 2.9 +/- 1.9 mL/kg/min [Elderly (65-75 yrs)]
ToxicityWith drugs of this type, muscarine-like symptoms (nausea, vomiting, diarrhea, sweating, increased bronchial and salivary secretions and bradycardia) often appear with overdosage (cholinergic crisis).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier+0.8867
Caco-2 permeable+0.6827
P-glycoprotein substrateNon-substrate0.6628
P-glycoprotein inhibitor INon-inhibitor0.9814
P-glycoprotein inhibitor IINon-inhibitor0.9163
Renal organic cation transporterNon-inhibitor0.8132
CYP450 2C9 substrateNon-substrate0.7682
CYP450 2D6 substrateNon-substrate0.6247
CYP450 3A4 substrateSubstrate0.569
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9181
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.918
CYP450 3A4 inhibitorNon-inhibitor0.9523
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9202
Ames testAMES toxic0.6723
CarcinogenicityCarcinogens 0.5357
BiodegradationNot ready biodegradable0.903
Rat acute toxicity2.4293 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8461
hERG inhibition (predictor II)Non-inhibitor0.6585
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Watson laboratories inc
  • Bioniche pharma usa llc
  • Organon usa inc
  • Valeant pharmaceuticals international
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintramuscular; intravenous10 mg/mL
Liquidintravenous10 mg
Injection, solutionintravenous
Liquidintramuscular; intravenous10 mg
Prices
Unit descriptionCostUnit
Enlon-plus multi-dose vial1.92USD ml
Enlon-plus ampul1.87USD ml
Enlon 10 mg/ml vial0.69USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point162-163Terrell, R.C.; U.S. Patents 3,469,011; September 23, 1969 and 3,527,813; September 8, 1970; both assigned to Air Reduction Company, Incorporated.
water solubilityAppreciable as liquid hydrochloride saltNot Available
logP-2.95Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0486 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Terrell, R.C.; U.S. Patents 3,469,011; September 23, 1969 and 3,527,813; September 8,
1970; both assigned to Air Reduction Company, Incorporated.

General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 36:56.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (50.8 KB)
Interactions
Drug Interactions
Drug
AcetylcholineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Acetylcholine.
Atracurium besylateEdrophonium may decrease the neuromuscular blocking activities of Atracurium besylate.
CarbacholThe risk or severity of adverse effects can be increased when Edrophonium is combined with Carbachol.
DigoxinEdrophonium may increase the atrioventricular blocking (AV block) activities of Digoxin.
DipyridamoleThe therapeutic efficacy of Edrophonium can be decreased when used in combination with Dipyridamole.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Edrophonium.
NadololEdrophonium may increase the bradycardic activities of Nadolol.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Edrophonium.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Edrophonium.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine hydrolase 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 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Identical protein binding
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 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23