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Identification
Name Edrophonium
Accession Number DB01010 (APRD00944)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • EDR
  • Edrophone Chloride
  • Edrophonium Chloride
  • Edrophonium Ion
  • Edrophonum
Brand names
  • Antirex
  • Enlon
  • Enlon Plus
  • Reversol
  • Tensilon
  • Tensilon chloride
Brand name mixtures Not Available
Categories
  • Cholinesterase Inhibitors
  • Antidotes
CAS number 116-38-1
Weight Average: 166.2401
Monoisotopic: 166.123189139
Chemical Formula C10H16NO
InChI Key InChIKey=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
Plain Text
IUPAC Name
N-ethyl-3-hydroxy-N,N-dimethylanilinium
SMILES
CC[N+](C)(C)C1=CC(O)=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Aminophenols and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Aminophenols and Derivatives
  • Quaternary Ammonium Salts
  • Aromatic compounds
  • Phenyl Esters
  • Anilines
  • Cations
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.
Pharmacodynamics 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. Muscarinic 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 muscarinic 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 acetyl choline 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.
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
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)]
Toxicity 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).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Watson laboratories inc
  • Bioniche pharma usa llc
  • Organon usa inc
  • Valeant pharmaceuticals international
Packagers
Dosage forms
Form Route Strength
Liquid Intramuscular
Liquid Intravenous
Prices
Unit description Cost Unit
Enlon-plus multi-dose vial 1.92 USD ml
Enlon-plus ampul 1.87 USD ml
Enlon 10 mg/ml vial 0.69 USD ml
Patents Not Available
Properties
State liquid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Appreciable as liquid hydrochloride salt PhysProp
logP -2.95 PhysProp
Predicted Properties
Property Value Source
water solubility 4.86e-02 g/l ALOGPS
logP -1.55 ALOGPS
logP -1.91 ChemAxon Molconvert
logS -3.62 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 20.23 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 62.41 ChemAxon Molconvert
polarizability 19.15 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C06976 Link_out
PubChem Compound 3202 Link_out
PubChem Substance 46507530 Link_out
ChemSpider 3090 Link_out
ChEBI 251408 Link_out
ChEMBL 251408 Link_out
Therapeutic Targets Database DAP000562 Link_out
PharmGKB PA449437 Link_out
HET EDR Link_out
Drug Product Database 2188848 Link_out
RxList http://www.rxlist.com/cgi/generic3/edrophonium.htm Link_out
Drugs.com http://www.drugs.com/mtm/edrophonium.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Edrophonium Link_out
ATC Codes Not Available
AHFS Codes
  • 36:56.00
PDB Entries Not Available
FDA label Not Available
MSDS show (50.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Acetylcholinesterase

Pharmacological action: yes
Actions: inhibitor

Rapidly hydrolyzes choline released into the synapse

Organism class: human
UniProt ID: P22303 Link_out
Gene: ACHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Cholinesterase

Pharmacological action: yes
Actions: inhibitor

An acylcholine + H(2)O = choline + a carboxylate

Organism class: human
UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on August 18, 2011 11:14

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.