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Identification
NameEdrophonium
Accession NumberDB01010  (APRD00944)
TypeSmall Molecule
GroupsApproved
DescriptionA 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 KeyVWLHWLSRQJQWRG-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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
AcetylcholinesteraseProteinyes
inhibitor
HumanP22303 details
CholinesteraseProteinyes
inhibitor
HumanP06276 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Edrophonium.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Edrophonium.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Edrophonium.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Edrophonium.Experimental, Illicit
AcebutololEdrophonium may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Acetylcholine.Approved
AcetyldigitoxinEdrophonium may increase the atrioventricular blocking (AV block) activities of Acetyldigitoxin.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Edrophonium.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Edrophonium.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Edrophonium.Experimental
AlprenololEdrophonium may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Edrophonium.Approved
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Edrophonium.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Edrophonium.Approved
AnvirzelEdrophonium may increase the atrioventricular blocking (AV block) activities of Anvirzel.Investigational
Aop200704Edrophonium may increase the bradycardic activities of Aop200704.Investigational
ArecolineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Arecoline.Experimental
ArotinololEdrophonium may increase the bradycardic activities of Arotinolol.Approved
AtenololEdrophonium may increase the bradycardic activities of Atenolol.Approved
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Edrophonium.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Edrophonium.Approved, Vet Approved
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Edrophonium.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Edrophonium.Approved, Investigational
BefunololEdrophonium may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Edrophonium.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Edrophonium.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Edrophonium.Approved, Vet Approved
BetaxololEdrophonium may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Edrophonium is combined with Bethanechol.Approved
BevantololEdrophonium may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Edrophonium.Approved
BisoprololEdrophonium may increase the bradycardic activities of Bisoprolol.Approved
BopindololEdrophonium may increase the bradycardic activities of Bopindolol.Approved
BucindololEdrophonium may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Edrophonium.Approved
BufuralolEdrophonium may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololEdrophonium may increase the bradycardic activities of Bupranolol.Approved
CarbacholThe risk or severity of adverse effects can be increased when Edrophonium is combined with Carbachol.Approved
CarteololEdrophonium may increase the bradycardic activities of Carteolol.Approved
CarvedilolEdrophonium may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololEdrophonium may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Edrophonium.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Edrophonium.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Edrophonium.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Edrophonium.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Edrophonium.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Edrophonium.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Edrophonium.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Edrophonium.Approved, Investigational
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Edrophonium.Investigational
DeslanosideEdrophonium may increase the atrioventricular blocking (AV block) activities of Deslanoside.Approved
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Edrophonium.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Edrophonium.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Edrophonium.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Edrophonium.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Edrophonium.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Edrophonium.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Edrophonium.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Edrophonium.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Edrophonium.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Edrophonium.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Edrophonium.Approved
DigitoxinEdrophonium may increase the atrioventricular blocking (AV block) activities of Digitoxin.Approved
DigoxinEdrophonium may increase the atrioventricular blocking (AV block) activities of Digoxin.Approved
DipyridamoleThe therapeutic efficacy of Edrophonium can be decreased when used in combination with Dipyridamole.Approved
EPIBATIDINEThe risk or severity of adverse effects can be increased when Edrophonium is combined with EPIBATIDINE.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Edrophonium.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Edrophonium.Approved
EsmololEdrophonium may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Edrophonium.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Edrophonium.Approved
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Edrophonium.Approved
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Edrophonium.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Edrophonium.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Edrophonium.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Edrophonium.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Edrophonium.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Edrophonium.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Edrophonium.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Edrophonium.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Edrophonium.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Edrophonium.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Edrophonium.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Edrophonium.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Edrophonium.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Edrophonium.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Edrophonium.Approved, Investigational, Withdrawn
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Edrophonium.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Edrophonium.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Edrophonium is combined with GTS-21.Investigational
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Edrophonium.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Edrophonium.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Edrophonium.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Edrophonium.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Edrophonium.Approved
IndenololEdrophonium may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Edrophonium.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Edrophonium.Investigational
LabetalolEdrophonium may increase the bradycardic activities of Labetalol.Approved
LevobunololEdrophonium may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Lobeline.Investigational
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Edrophonium.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Edrophonium.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Edrophonium.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Edrophonium.Vet Approved
MethacholineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Edrophonium.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Edrophonium.Approved, Vet Approved
MetipranololEdrophonium may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Edrophonium.Approved
MetoprololEdrophonium may increase the bradycardic activities of Metoprolol.Approved, Investigational
MivacuriumEdrophonium may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Edrophonium.Approved, Vet Approved
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Edrophonium.Vet Approved
NadololEdrophonium may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Edrophonium.Investigational
NicotineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Nicotine.Approved
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Edrophonium is combined with Nicotine bitartrate.Approved
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Edrophonium.Investigational
Oleoyl estroneThe risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Edrophonium.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Edrophonium.Approved
OuabainEdrophonium may increase the atrioventricular blocking (AV block) activities of Ouabain.Approved
OxprenololEdrophonium may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Edrophonium.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Edrophonium.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Edrophonium.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Edrophonium.Approved
PenbutololEdrophonium may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Edrophonium.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Pilocarpine.Approved
PindololEdrophonium may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Edrophonium.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Edrophonium.Approved
PractololEdrophonium may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Edrophonium.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Edrophonium.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Edrophonium.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Edrophonium.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Edrophonium.Experimental
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Edrophonium.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Edrophonium.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Edrophonium.Investigational
PropranololEdrophonium may increase the bradycardic activities of Propranolol.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Edrophonium.Approved
RapacuroniumEdrophonium may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Edrophonium.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Edrophonium.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Edrophonium.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Edrophonium.Approved
SotalolEdrophonium may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Edrophonium.Approved
TimololEdrophonium may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Edrophonium.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Edrophonium.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Edrophonium.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Edrophonium.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Edrophonium.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Edrophonium.Approved
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Edrophonium.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Edrophonium.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Edrophonium.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Edrophonium.Approved
VareniclineThe risk or severity of adverse effects can be increased when Edrophonium is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Edrophonium.Approved
Food InteractionsNot 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)
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
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

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