Identification
- Summary
Edrophonium is a cholinesterase inhibitor used to diagnose and evaluate myasthenia gravis.
- Brand Names
- Enlon, Enlon-plus
- Generic Name
- Edrophonium
- DrugBank Accession Number
- DB01010
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Edrophonium (DB01010)
- Weight
- Average: 166.2401
Monoisotopic: 166.123189139 - Chemical Formula
- C10H16NO
- Synonyms
- (3-hydroxyphenyl)dimethylethylammonium
- 3-hydroxy-N,N-dimethyl-N-ethylanilinium
- Edrophonium cation
- Edrophonium ion
- Ethyl-(3-hydroxy-phenyl)-dimethyl-ammonium
- N-ethyl-3-hydroxy-N,N-dimethylanilinium
- N-ethyl-3-hydroxy-N,N-dimethylbenzenaminium
Pharmacology
- Indication
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Myasthenia gravis •••••••••••• Reversal of Neuromuscular block •••••••••••• Reversal of Neuromuscular block •••••••••••• Reversal of Neuromuscular block •••••••••••• Reversal of Neuromuscular block •••••••••••• - Contraindications & Blackbox Warnings
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Edrophonium 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 action
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 stimulates nicotinic and muscarinic receptors. When stimulated, these receptors have a range of effects.
Target Actions Organism ACholinesterase inhibitorHumans AAcetylcholinesterase inhibitorHumans - Absorption
Rapidly 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 binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Edrophonium 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-life
Distribution 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)]
- Adverse Effects
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With drugs of this type, muscarine-like symptoms (nausea, vomiting, diarrhea, sweating, increased bronchial and salivary secretions and bradycardia) often appear with overdosage (cholinergic crisis).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Edrophonium may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol Edrophonium may increase the bradycardic activities of Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Edrophonium which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Edrophonium which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Edrophonium which could result in a higher serum level. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Edrophonium bromide KX008093VW 302-83-0 CAEPIUXAUPYIIJ-UHFFFAOYSA-N Edrophonium chloride QO611KSM5P 116-38-1 BXKDSDJJOVIHMX-UHFFFAOYSA-N - International/Other Brands
- Antirex (Kyorin) / Reversol
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Enlon Injection 10 mg/1mL Intramuscular; Intravenous Baxter Laboratories 2006-10-17 Not applicable US 
Enlon 10mg/ml Liquid 10 mg / mL Intravenous Baxter Laboratories 1996-09-18 2008-01-28 Canada 
Enlon Liq IV 10mg/ml Liquid 10 mg / mL Intravenous Ohmeda Pharmaceutical Products, Division Of Boc Canada Limited 1995-12-31 1996-09-26 Canada Tensilon Liquid 10 mg / mL Intramuscular; Intravenous Valeant Canada Lp Valeant Canada S.E.C. 1988-12-31 2016-07-08 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Enlon Injection, solution 10 mg/1mL Intramuscular; Intravenous Mylan Institutional LLC 2013-04-22 2018-05-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Enlon Plus Edrophonium chloride (10 mg/1mL) + Atropine sulfate (0.14 mg/1mL) Injection, solution Intravenous Mylan Institutional LLC 1991-11-06 2017-12-31 US Enlon Plus Edrophonium chloride (10 mg/1mL) + Atropine sulfate anhydrous (0.14 mg/1mL) Injection, solution Intravenous Bioniche Pharma USA LLC 2008-10-01 2009-11-25 US Enlon-Plus Edrophonium chloride (10.0 mg/1.0mL) + Atropine sulfate (0.14 mg/1.0mL) Injection Intravenous Baxter Healthcare Corporation 2006-03-09 Not applicable US Enlon-Plus Edrophonium chloride (10 mg/1mL) + Atropine sulfate (0.14 mg/1.0mL) Injection Intravenous Baxter Healthcare Corporation 2006-03-09 Not applicable US
Categories
- ATC Codes
- V04CX07 — Edrophonium
- Drug Categories
- Amines
- Antidotes
- Cholinergic Agents
- Cholinesterase Inhibitors
- Compounds used in a research, industrial, or household setting
- Diagnostic Agents
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Neurotransmitter Agents
- Onium Compounds
- Phenylammonium Compounds
- Protective Agents
- Quaternary Ammonium Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- 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
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Aminophenol / Aniline or substituted anilines / Aromatic homomonocyclic compound / Hydrocarbon derivative / M-aminophenol / Organic cation / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, quaternary ammonium ion (CHEBI:251408)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 70FP3JLY7N
- CAS number
- 312-48-1
- InChI Key
- 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
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015145
- KEGG Compound
- C06976
- PubChem Compound
- 3202
- PubChem Substance
- 46507530
- ChemSpider
- 3090
- BindingDB
- 120262
- 3752
- ChEBI
- 251408
- ChEMBL
- CHEMBL1104
- ZINC
- ZINC000000001341
- Therapeutic Targets Database
- DAP000562
- PharmGKB
- PA449437
- PDBe Ligand
- EDR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Edrophonium
- PDB Entries
- 1ax9 / 2ack
- MSDS
- Download (50.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Completed Screening Disorders of the Autonomic Nervous System / Dopamine Beta Hydroxylase Deficiency / Orthostatic Hypotension / Orthostatic Intolerance 1
Pharmacoeconomics
- Manufacturers
- Hospira inc
- Watson laboratories inc
- Bioniche pharma usa llc
- Organon usa inc
- Valeant pharmaceuticals international
- Packagers
- Akorn Inc.
- Baxter International Inc.
- Bioniche Pharma
- Taylor Pharmaceuticals
- Valeant Ltd.
- Dosage Forms
Form Route Strength Injection Intramuscular; Intravenous 10 mg/1mL Injection, solution Intramuscular; Intravenous 10 mg/1mL Liquid Intravenous 10 mg / mL Injection, solution Intravenous Injection Intravenous Liquid Intramuscular; Intravenous 10 mg / mL - Prices
Unit description Cost Unit Enlon-plus multi-dose vial 1.92USD ml Enlon-plus ampul 1.87USD ml Enlon 10 mg/ml vial 0.69USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 162-163 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. water solubility Appreciable as liquid hydrochloride salt Not Available logP -2.95 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0486 mg/mL 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8406 Blood Brain Barrier + 0.8867 Caco-2 permeable + 0.6827 P-glycoprotein substrate Non-substrate 0.6628 P-glycoprotein inhibitor I Non-inhibitor 0.9814 P-glycoprotein inhibitor II Non-inhibitor 0.9163 Renal organic cation transporter Non-inhibitor 0.8132 CYP450 2C9 substrate Non-substrate 0.7682 CYP450 2D6 substrate Non-substrate 0.6247 CYP450 3A4 substrate Substrate 0.569 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9181 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.918 CYP450 3A4 inhibitor Non-inhibitor 0.9523 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9202 Ames test AMES toxic 0.6723 Carcinogenicity Carcinogens 0.5357 Biodegradation Not ready biodegradable 0.903 Rat acute toxicity 2.4293 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8461 hERG inhibition (predictor II) Non-inhibitor 0.6585
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-1900000000-416237a97b8a91587c90 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.4984339 predictedDarkChem Lite v0.1.0 [M-H]- 130.59651 predictedDeepCCS 1.0 (2019) [M+H]+ 142.2632339 predictedDarkChem Lite v0.1.0 [M+H]+ 132.9923 predictedDeepCCS 1.0 (2019) [M+Na]+ 141.6746339 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.90868 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:47