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
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
Myasthenia syndrome during penicillamine treatment.
1975 Jun 28
Myasthenia associated with D-penicillamine therapy in rheumatoid arthritis.
1977
[Prognostic factors and outcome of thymectomy in 80 cases of myasthenia gravis].
2001 Apr
Electrogastrography: a non-invasive measurement of gastric function.
2001 Apr-Jun
[A patient with facioscapulohumeral muscular dystrophy accompanied by myasthenia gravis].
2001 Apr-May
Focal myopathy mimicking posterior interosseous nerve syndrome.
2001 Jul
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
Tensilon and the diagnosis of myasthenia gravis: are we using the Tensilon test too much?
2001 Sep
Respiratory failure due to vocal cord paresis in myasthenia gravis.
2002
Clinical, electrophysiological and immunological remissions after thymectomy in myasthenia gravis.
2002 Apr
Purification of soluble acetylcholinesterase from Japanese quail brain by affinity chromatography.
2002 Feb
Effects of the anticholinesterase edrophonium on spectral analysis of heart rate and blood pressure variability in humans.
2002 Jan
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
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
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
Natural monomeric form of fetal bovine serum acetylcholinesterase lacks the C-terminal tetramerization domain.
2003 Dec 30
Esophageal manometry in patients with clinical symptoms mimicking esophageal origin: a hospital-based ten-year experience.
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
Endplate dysfunction causing respiratory failure in a patient with prior paralytic poliomyelitis.
2003 Mar
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
Antinociception of intrathecal cholinesterase inhibitors and cholinergic receptors in rats.
2003 Oct
Myasthenia gravis in childhood.
2004
Appearance of systemic lupus erythematosus in patients with myasthenia gravis following thymectomy: two case reports.
2004 Feb
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
Response of thymectomy: clinical and pathological characteristics among seronegative and seropositive myasthenia gravis patients.
2004 Mar
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
Advances in the diagnosis of neuromuscular junction disorders.
2005 Aug
Edrophonium-induced right ventricular outflow tract tachycardia.
2005 Jan
Clinical utility of videofluorography with concomitant Tensilon administration in the diagnosis of bulbar myasthenia gravis.
2005 May
MG and LEMS overlap syndrome: case report with electrophysiological and immunological evidence.
2005 May
Management of myasthenia gravis.
2005 May-Jun
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
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
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Code System Code Type Description
NCI_THESAURUS
C47507
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PRIMARY
EPA CompTox
DTXSID1022978
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PRIMARY
CHEBI
4759
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PRIMARY
SMS_ID
100000080513
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PRIMARY
DRUG BANK
DBSALT000475
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PRIMARY
INN
187
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
EDROPHONIUM CHLORIDE
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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
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PRIMARY
FDA UNII
QO611KSM5P
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PRIMARY
ChEMBL
CHEMBL1104
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PRIMARY
CAS
116-38-1
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PRIMARY
RS_ITEM_NUM
1234001
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PRIMARY
MERCK INDEX
m4834
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PRIMARY Merck Index
PUBCHEM
8307
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PRIMARY
EVMPD
SUB06461MIG
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PRIMARY
NSC
759577
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PRIMARY
DAILYMED
QO611KSM5P
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PRIMARY
RXCUI
3754
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PRIMARY RxNorm