U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16NO.Cl
Molecular Weight 201.693
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDROPHONIUM CHLORIDE

SMILES

[Cl-].CC[N+](C)(C)C1=CC(O)=CC=C1

InChI

InChIKey=BXKDSDJJOVIHMX-UHFFFAOYSA-N
InChI=1S/C10H15NO.ClH/c1-4-11(2,3)9-6-5-7-10(12)8-9;/h5-8H,4H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula C10H15NO
Molecular Weight 165.2322
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Edrophonium is a short and rapid-acting cholinergic drug. Chemically, edrophonium is ethyl (m-hydroxyphenyl) dimethylammonium. Edrophonium is used 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. Because of its brief duration of action, it is not recommended for maintenance therapy in myasthenia gravis. It is also useful whenever a curare antagonist is needed to reverse the neuromuscular block produced by curare, tubocurarine, gallamine triethiodide or dimethyl-tubocurarine. It is not effective against decamethonium bromide and succinylcholine chloride. It may be used adjunctively in the treatment of respiratory depression caused by curare overdosage.

Originator

Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/edrophonium-chloride.html # Hoffmann La Roche

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
ENLON

Approved Use

Enlon (edrophonium injection) ® is recommended 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. Because of its brief duration of action, it is not recommended for maintenance therapy in myasthenia gravis. Enlon (edrophonium injection) ® is also useful whenever a curare antagonist is needed to reverse the neuromuscular block produced by curare, tubocurarine, gallamine triethiodide or dimethyl-tubocurarine. It is not effective against decamethonium bromide and succinylcholine chloride. It may be used adjunctively in the treatment of respiratory depression caused by curare overdosage.

Launch Date

1985
Preventing
ENLON

Approved Use

Enlon (edrophonium injection) ® is recommended 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. Because of its brief duration of action, it is not recommended for maintenance therapy in myasthenia gravis. Enlon (edrophonium injection) ® is also useful whenever a curare antagonist is needed to reverse the neuromuscular block produced by curare, tubocurarine, gallamine triethiodide or dimethyl-tubocurarine. It is not effective against decamethonium bromide and succinylcholine chloride. It may be used adjunctively in the treatment of respiratory depression caused by curare overdosage.

Launch Date

1985
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
110 min
0.5 mg/kg single, intravenous
dose: 0.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ATROPINE
EDROPHONIUM blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
110 min
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ATROPINE
EDROPHONIUM blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
56.6 min
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ATROPINE
EDROPHONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
84.2 min
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: ATROPINE
EDROPHONIUM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Train-of-four nerve stimulation in the management of prolonged neuromuscular blockade following succinylcholine.
1975 Jan
Myasthenia associated with D-penicillamine therapy in rheumatoid arthritis.
1977
Determination of inhibitors' potency (IC50) by a direct high-performance liquid chromatographic method on an immobilised acetylcholinesterase column.
2001 Apr 5
Electrogastrography: a non-invasive measurement of gastric function.
2001 Apr-Jun
[A patient of chronic graft-versus-host disease presenting simultaneously with polymyositis and myasthenia gravis].
2001 Aug
Edrophonium antagonism of cisatracurium-induced neuromuscular block: dose requirements in children and adults.
2001 Aug
Effect of chemical modification of recombinant human acetylcholinesterase by polyethylene glycol on its circulatory longevity.
2001 Aug 1
A dose-response study of anticholinesterase drugs on contractile and phosphatidylinositol responses of rat trachea.
2001 Jan
Does "butyrylization" of acetylcholinesterase through substitution of the six divergent aromatic amino acids in the active center gorge generate an enzyme mimic of butyrylcholinesterase?
2001 Jun 26
Laryngeal myasthenia gravis: report of 40 cases.
2001 Mar
Interaction of edrophonium with muscarinic acetylcholine M2 and M3 receptors.
2001 May
Autosomal recessive limb girdle myasthenia in two sisters.
2002 Dec
Effects of the anticholinesterase edrophonium on spectral analysis of heart rate and blood pressure variability in humans.
2002 Jan
[Myasthenia gravis].
2002 Jan 1
Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block.
2002 Jan 21
[Thymectomy in juvenile myasthenia gravis].
2002 Jul 16-31
[What to do in case of acquired ptosis].
2002 Mar
Respiratory chain complex-I defect mimicking myasthenia.
2002 Mar
The effect of edrophonium on autonomic outflow.
2002 Mar
Markedly enhanced susceptibility to experimental autoimmune myasthenia gravis in the absence of decay-accelerating factor protection.
2002 Nov
Catalytic antibodies with acetylcholinesterase activity.
2002 Nov 1
A comparison of the chronotropic and dromotropic actions between adenosine triphosphate and edrophonium in patients undergoing coronary artery bypass graft surgery.
2002 Oct
Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase.
2003 Apr
[Comparison between idiopathic achalasia and achalasia caused by Chagas' disease: a review on the publications about the subject].
2003 Apr-Jun
[Blepharospasm in a patient with thymoma and positive anti-acetylcholine receptor antibody].
2003 Aug
Ocular myasthenia gravis associated with euthyroid ophthalmopathy.
2003 Dec
Natural monomeric form of fetal bovine serum acetylcholinesterase lacks the C-terminal tetramerization domain.
2003 Dec 30
Development of generalized disease at 2 years in patients with ocular myasthenia gravis.
2003 Feb
beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies.
2003 Feb 1
Esophageal manometry in patients with clinical symptoms mimicking esophageal origin: a hospital-based ten-year experience.
2003 Jan
Simplified tilt table test protocol with continuous upright position during medication administration and no hydration.
2003 Jan
Positive tensilon test and intracranial tumor: a case report.
2003 Jul
Chiropractic care of a pediatric patient with myasthenia gravis.
2003 Jul-Aug
Utility of ambulatory 24-hour esophageal pH and motility monitoring in noncardiac chest pain: report of 90 patients and review of the literature.
2003 May
Assessment of esophageal function in patients with myasthenia gravis.
2003 May
Facile synthesis of [11C]edrophonium and its analogues as new potential PET imaging agents for heart acetylcholinesterase.
2003 May 19
[Response to thymectomy in patients with thymoma].
2003 Nov-Dec
Clinical correlates with anti-MuSK antibodies in generalized seronegative myasthenia gravis.
2003 Oct
Myasthenia gravis in childhood.
2004
Anticholinesterase therapy for patients with ophthalmoplegia following snake bites: report of two cases.
2004 Aug
Clinical and neurophysiological characteristics of congenital myasthenic syndromes presenting in early infancy.
2004 Jan
Does acetylcholinesterase inhibition affect catecholamine secretion by adrenomedullary cells?
2004 Jul
[A case of transient left ventricular ballooning ("Takotsubo"-shaped cardiomyopathy) developed during plasmapheresis for treatment of myasthenic crisis].
2004 Mar
Nitric oxide and cardiac muscarinic control in humans.
2004 May
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
2004 Oct
Immunological and electrophysiological investigations of severe ptosis after bone marrow transplantation.
2004 Sep
Frequency of myasthenic crisis in relation to thymectomy in generalized myasthenia gravis: a 17-year experience.
2004 Sep 11
Does this patient have myasthenia gravis?
2005 Apr 20
Advances in the diagnosis of neuromuscular junction disorders.
2005 Aug
Postinfectious myasthenia gravis: report of two children.
2005 May
Patents

Sample Use Guides

In Vivo Use Guide
Enlon (edrophonium injection) ® Test in the Differential Diagnosis of Myasthenia Gravis:1-8 Intravenous Dosage (Adults): A tuberculin syringe containing 1 mL (10 mg) of Enlon (edrophonium injection) ® is prepared with an intravenous needle, and 0.2 mL (2 mg) is injected intravenously within 15 to 30 seconds. The needle is left in situ. Only if no reaction occurs after 45 seconds is the remaining 0.8 mL (8 mg) injected. If a cholinergic reaction (muscarinic side effects, skeletal muscle fasciculations and increased muscle weakness) occurs after injection of 0.2 mL (2 mg), the test is discontinued and atropine sulfate, 0.4 mg to 0.5 mg, is administered intravenously. After one-half hour the test may be repeated. Intramuscular Dosage (Adults): In adults with inaccessible veins, dosage for intramuscular injection is 1 mL (10 mg) of Enlon (edrophonium injection) ®. Subjects who demonstrate hyperreactivity to this injection (cholinergic reaction), should be retested after one-half hour with 0.2 mL (2mg) of Enlon (edrophonium injection) ® intramuscularly to rule out false-negative reactions. For Use as a Curare Antagonist: Enlon (edrophonium injection) ® should be administered by intravenous injection in 1 mL (10 mg) doses given slowly over a period of 30 to 45 seconds so that the onset of cholinergic reaction can be detected. This dosage may be repeated whenever necessary. The maximal dose for any one patient should be 4 mL (40 mg). Because of its brief effect, Enlon (edrophonium injection) ® should not be given prior to the administration of curare, tubocurarine, gallamine triethiodide or dimethyl-tubocurarine: it should be used at the time when its effect is needed. When given to counteract curare overdosage, the effect of each dose on the respiration should be carefully observed before it is repeated, and assisted ventilation should always be employed.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:13:50 GMT 2023
Edited
by admin
on Sat Dec 16 16:13:50 GMT 2023
Record UNII
QO611KSM5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EDROPHONIUM CHLORIDE
EP   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
ENLON
Brand Name English
EDROPHONIUM CHLORIDE [USP-RS]
Common Name English
EDROPHONIUM CHLORIDE [USP MONOGRAPH]
Common Name English
EDROPHONIUM CHLORIDE [EP MONOGRAPH]
Common Name English
EDROPHONIUM CHLORIDE [MI]
Common Name English
Edrophonium chloride [WHO-DD]
Common Name English
EDROPHONIUM CHLORIDE [JAN]
Common Name English
NSC-759577
Code English
EDROPHONIUM CHLORIDE [VANDF]
Common Name English
EDROPHONIUM CHLORIDE [ORANGE BOOK]
Common Name English
EDROPHONIUM CHLORIDE [WHO-IP]
Common Name English
BENZENAMINIUM, N-ETHYL-3-HYDROXY-N,N-DIMETHYL-, CHLORIDE
Systematic Name English
edrophonium chloride [INN]
Common Name English
ETHYL(M-HYDROXYPHENYL)DIMETHYLAMMONIUM CHLORIDE
Systematic Name English
ENLON-PLUS COMPONENT EDROPHONIUM CHLORIDE
Common Name English
EDROPHONIUM CHLORIDE COMPONENT OF ENLON-PLUS
Common Name English
EDROPHONIUM CHLORIDE [MART.]
Common Name English
TENSILON
Brand Name English
ANTIREX
Common Name English
REVERSOL
Brand Name English
EDROPHONII CHLORIDUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C47507
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID1022978
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
CHEBI
4759
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
SMS_ID
100000080513
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
DRUG BANK
DBSALT000475
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
INN
187
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EDROPHONIUM CHLORIDE
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY Description: A white, crystalline powder; odourless.Solubility: Soluble in 0.5 parts of water and in 5 parts of ethanol (~750 g/l) TS; practically insoluble in ether R.Category: Diagnostic agent.Storage: Edrophonium chloride should be kept in a well-closed container, protected from light.Requirements: Definition. Edrophonium chloride contains not less than 98.5% and not more than 101.0% of C10H16ClNO, calculated withreference to the dried substance.
ECHA (EC/EINECS)
204-138-4
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
FDA UNII
QO611KSM5P
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL1104
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
CAS
116-38-1
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
RS_ITEM_NUM
1234001
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
MERCK INDEX
m4834
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY Merck Index
PUBCHEM
8307
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
EVMPD
SUB06461MIG
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
NSC
759577
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
DAILYMED
QO611KSM5P
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY
RXCUI
3754
Created by admin on Sat Dec 16 16:13:50 GMT 2023 , Edited by admin on Sat Dec 16 16:13:50 GMT 2023
PRIMARY RxNorm
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