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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16NO
Molecular Weight 166.2405
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of EDROPHONIUM

SMILES

CC[N+](C)(C)c1cccc(c1)O

InChI

InChIKey=VWLHWLSRQJQWRG-UHFFFAOYSA-O
InChI=1S/C10H15NO/c1-4-11(2,3)9-6-5-7-10(12)8-9/h5-8H,4H2,1-3H3/p+1

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

4.92047991E11
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

4.92047991E11
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
[A patient of chronic graft-versus-host disease presenting simultaneously with polymyositis and myasthenia gravis].
2001 Aug
Reversal of mivacurium chloride: edrophonium of spontaneous recovery in microscopic laryngeal surgery.
2001 Dec
Laryngeal myasthenia gravis: report of 40 cases.
2001 Mar
[Giant-cell myocarditis without a symptom of heart failure seen in a patient with myasthenia gravis and concurrent Hashimoto's disease].
2001 Nov
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
Autosomal recessive limb girdle myasthenia in two sisters.
2002 Dec
Purification of soluble acetylcholinesterase from Japanese quail brain by affinity chromatography.
2002 Feb
[Technical consideration for repetitive nerve stimulation].
2002 Jan
Effects of the anticholinesterase edrophonium on spectral analysis of heart rate and blood pressure variability in humans.
2002 Jan
[Myasthenia gravis].
2002 Jan 1
[Ocular myasthenic syndrome and systemic lupus erythematosus].
2002 Jul
[Thymectomy in juvenile myasthenia gravis].
2002 Jul 16-31
[What to do in case of acquired ptosis].
2002 Mar
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
Idiotypic mimicry of a catalytic antibody active site.
2002 Oct
Potencies and selectivities of inhibitors of acetylcholinesterase and its molecular forms in normal and Alzheimer's disease brain.
2003
[Premonitory depression].
2003
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
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
Clinical profile of myasthenia gravis in the Sultanate of Oman.
2003 Jul
Chiropractic care of a pediatric patient with myasthenia gravis.
2003 Jul-Aug
The edrophonium test.
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
Edrophonium effectively antagonizes neuromuscular block at the laryngeal adductors induced by rapacuronium, rocuronium and cisatracurium, but not mivacurium.
2003 Nov
Antinociception of intrathecal cholinesterase inhibitors and cholinergic receptors in rats.
2003 Oct
Clinical correlates with anti-MuSK antibodies in generalized seronegative myasthenia gravis.
2003 Oct
Cage amines as the stopper inhibitors of cholinesterases.
2003 Sep 1
Mutation in the AChR ion channel gate underlies a fast channel congenital myasthenic syndrome.
2004 Apr 13
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
Persistent diplopia after retrobulbar anesthesia.
2004 Jun
[A case of transient left ventricular ballooning ("Takotsubo"-shaped cardiomyopathy) developed during plasmapheresis for treatment of myasthenic crisis].
2004 Mar
A case of Lambert-Eaton myasthenic syndrome associated with atypical bronchopulmonary carcinoid tumor.
2004 Oct
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
2004 Oct
Pupil-sparing, painless compression of the oculomotor nerve by expanding basilar artery aneurysm: a case of ocular pseudomyasthenia.
2004 Sep
Ocular myasthenia gravis.
2004 Sep
'Dropped head sign' in myasthenia gravis.
2004 Sep
Sensory testing of the esophagus.
2004 Sep
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
MG and LEMS overlap syndrome: case report with electrophysiological and immunological evidence.
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
Name Type Language
EDROPHONIUM
VANDF   WHO-DD  
Common Name English
BENZENAMINIUM, N-ETHYL-3-HYDROXY-N,N-DIMETHYL-
Systematic Name English
EDROPHONIUM [WHO-DD]
Common Name English
EDROPHONIUM [VANDF]
Common Name English
ETHYL(M-HYDROXYPHENYL)DIMETHYLAMMONIUM
Systematic Name English
EDROPHONIUM ION
Common Name English
EDROPHONIUM CATION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
NDF-RT N0000175723
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
NDF-RT N0000000177
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
Code System Code Type Description
RXCUI
1546421
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
ALTERNATIVE
CAS
312-48-1
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
PUBCHEM
3202
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
RXCUI
3752
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
LACTMED
Edrophonium
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
WIKIPEDIA
Edrophonium
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
MESH
D004491
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
FDA UNII
70FP3JLY7N
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
EVMPD
SUB01860MIG
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
EPA CompTox
312-48-1
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
DRUG BANK
DB01010
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
DRUG CENTRAL
988
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY
NCI_THESAURUS
C76137
Created by admin on Sat Jun 26 01:15:50 UTC 2021 , Edited by admin on Sat Jun 26 01:15:50 UTC 2021
PRIMARY