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

Details

Stereochemistry ACHIRAL
Molecular Formula C28H42Cl2N4O2.2Cl
Molecular Weight 608.471
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMBENONIUM CHLORIDE

SMILES

[Cl-].[Cl-].CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=C(Cl)C=CC=C1)CC2=C(Cl)C=CC=C2

InChI

InChIKey=DXUUXWKFVDVHIK-UHFFFAOYSA-N
InChI=1S/C28H40Cl2N4O2.2ClH/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30;;/h9-16H,5-8,17-22H2,1-4H3;2*1H

HIDE SMILES / InChI

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

Molecular Formula C28H42Cl2N4O2
Molecular Weight 537.565
Charge 2
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ambenonium is a cholinesterase inhibitor with all the pharmacologic actions of acetylcholine, both the muscarinic and nicotinic types. It was marketed under the brand name Mytelase, but was withdrawn from the market in the United States in 2010. Ambenonium, similar to pyridostigmine and neostigmine, is used for the treatment of muscle weakness and fatigue in people with myasthenia gravis.Ambenonium exerts its actions against myasthenia gravis by competitive, reversible inhibition of acetylcholinesterase. The disease myasthenia gravis occurs when the body inappropriately produces antibodies against acetylcholine receptors, and thus inhibits proper acetylcholine signal transmission (when acetylcholine binds to acetylcholine receptors of striated muscle fibers, it stimulates those fibers to contract). Ambenonium reversibly binds acetylcholinesterase at the anionic site, which results in the blockage of the site of acetycholine binding, thereby inhibiting acetylcholine hydrolysis and enhancing cholinergic function through the accumulation of acetycholine at cholinergic synpases. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MYTELASE

Approved Use

This drug is indicated for the treatment of myasthenia gravis.

Launch Date

-4.31395209E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.129 μg/mL
10 mg 4 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.812 μg/mL
5 mg 4 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.29 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2.5 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
5.61 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
9.12 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8.4 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.38 μg × h/mL
10 mg 4 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6.5 μg × h/mL
5 mg 4 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
0.112 μg × min/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.23 μg × min/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.5 μg × min/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.07 μg × min/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBENONIUM serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
5 mg 4 times / day multiple, oral
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources:
unhealthy, 31 years
n = 1
Health Status: unhealthy
Condition: chronic cystitis
Age Group: 31 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Muscle weakness, Fatigue...
AEs leading to
discontinuation/dose reduction:
Muscle weakness (1 patient)
Fatigue (1 patient)
Chest pain (1 patient)
Sources:
10 mg 3 times / 2 days multiple, oral
Dose: 10 mg, 3 times / 2 days
Route: oral
Route: multiple
Dose: 10 mg, 3 times / 2 days
Sources:
unhealthy, 81 years
n = 1
Health Status: unhealthy
Condition: pernicious anemia
Age Group: 81 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Muscle weakness, Nausea...
AEs leading to
discontinuation/dose reduction:
Muscle weakness (1 patient)
Nausea (1 patient)
Abdominal pain (1 patient)
Sources:
1000 mg 1 times / day multiple, oral
Studied dose
Dose: 1000 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
AEs

AEs

AESignificanceDosePopulation
Chest pain 1 patient
Disc. AE
5 mg 4 times / day multiple, oral
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources:
unhealthy, 31 years
n = 1
Health Status: unhealthy
Condition: chronic cystitis
Age Group: 31 years
Sex: F
Population Size: 1
Sources:
Fatigue 1 patient
Disc. AE
5 mg 4 times / day multiple, oral
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources:
unhealthy, 31 years
n = 1
Health Status: unhealthy
Condition: chronic cystitis
Age Group: 31 years
Sex: F
Population Size: 1
Sources:
Muscle weakness 1 patient
Disc. AE
5 mg 4 times / day multiple, oral
Dose: 5 mg, 4 times / day
Route: oral
Route: multiple
Dose: 5 mg, 4 times / day
Sources:
unhealthy, 31 years
n = 1
Health Status: unhealthy
Condition: chronic cystitis
Age Group: 31 years
Sex: F
Population Size: 1
Sources:
Abdominal pain 1 patient
Disc. AE
10 mg 3 times / 2 days multiple, oral
Dose: 10 mg, 3 times / 2 days
Route: oral
Route: multiple
Dose: 10 mg, 3 times / 2 days
Sources:
unhealthy, 81 years
n = 1
Health Status: unhealthy
Condition: pernicious anemia
Age Group: 81 years
Sex: F
Population Size: 1
Sources:
Muscle weakness 1 patient
Disc. AE
10 mg 3 times / 2 days multiple, oral
Dose: 10 mg, 3 times / 2 days
Route: oral
Route: multiple
Dose: 10 mg, 3 times / 2 days
Sources:
unhealthy, 81 years
n = 1
Health Status: unhealthy
Condition: pernicious anemia
Age Group: 81 years
Sex: F
Population Size: 1
Sources:
Nausea 1 patient
Disc. AE
10 mg 3 times / 2 days multiple, oral
Dose: 10 mg, 3 times / 2 days
Route: oral
Route: multiple
Dose: 10 mg, 3 times / 2 days
Sources:
unhealthy, 81 years
n = 1
Health Status: unhealthy
Condition: pernicious anemia
Age Group: 81 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Effects of acetylcholinesterase inhibitors on the metabolism of amyloid precursor protein in vitro.
2001
Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors.
2001 Apr
Sequence of a cDNA encoding acetylcholinesterase from susceptible and resistant two-spotted spider mite, Tetranychus urticae.
2003 May
Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors.
2003 Sep
Activation of group II metabotropic glutamate receptors reduces directional selectivity in retinal ganglion cells.
2006 Nov 29
Concurrence of non-myasthenic symptoms with myasthenia gravis.
2007 Apr
Characterization of reversible and pseudo-irreversible acetylcholinesterase inhibitors by means of an immobilized enzyme reactor.
2007 Mar 9
Alpha6-containing nicotinic acetylcholine receptors dominate the nicotine control of dopamine neurotransmission in nucleus accumbens.
2008 Aug
Preoperative steroid therapy stabilizes postoperative respiratory conditions in myasthenia gravis.
2008 Mar
Preoperative steroid therapy stabilizes postoperative respiratory condition in myasthenia gravis.
2008 Mar
AChR deficiency due to epsilon-subunit mutations: two common mutations in the Netherlands.
2009 Oct
Patents

Patents

Sample Use Guides

For the patient with moderately severe myasthenia, from 5 mg to 25 mg of MYTELASE three or four times daily is an effective dose. In some patients a 5 mg dose is effective, whereas other patients require as much as from 50 mg to 75 mg per dose. The physician should start with a 5 mg dose, carefully observing the effect of the drug on the patient. The dosage may then be increased gradually to determine the effective and safe dose.
Route of Administration: Oral
In Vitro Use Guide
Inhibitory constant of ambenonium to bovine erythrocyte AChE determined in vitro was 3.7 nM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:50 UTC 2023
Edited
by admin
on Fri Dec 15 15:14:50 UTC 2023
Record UNII
51FOB87G3I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMBENONIUM CHLORIDE
INN   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
MYTELASE
Brand Name English
AMBENONIUM CHLORIDE [MI]
Common Name English
Ambenonium chloride [WHO-DD]
Common Name English
ambenonium chloride [INN]
Common Name English
AMBENONIUM CHLORIDE [ORANGE BOOK]
Common Name English
[Oxalylbis(iminoethylene)]bis[(O-chlorobenzyl)diethylammonium] dichloride
Common Name English
AMBENONIUM CHLORIDE [VANDF]
Common Name English
BENZENEMETHANAMINIUM, N,N'-((1,2-DIOXO-1,2-ETHANEDIYL)BIS(IMINO-2,1-ETHANEDIYL))BIS(2-CHLORO-N,N-DIETHYL-, DICHLORIDE
Systematic Name English
AMBENONIUM CHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
Code System Code Type Description
MESH
D000549
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL1652
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
WIKIPEDIA
AMBENONIUM CHLORIDE
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022582
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
RXCUI
624
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY RxNorm
CAS
115-79-7
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
FDA UNII
51FOB87G3I
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-107-5
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
SMS_ID
100000087666
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
NCI_THESAURUS
C47388
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
PUBCHEM
8288
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
MERCK INDEX
m1643
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001309
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
EVMPD
SUB05394MIG
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
CHEBI
2628
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
INN
552
Created by admin on Fri Dec 15 15:14:50 UTC 2023 , Edited by admin on Fri Dec 15 15:14:50 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
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ACTIVE MOIETY