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
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
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 It was marketed under the brand name Mytelase, but was withdrawn from the market in the United States in 2010.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.
CNS Activity
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.129 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1823874/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1823874/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2613842/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.38 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1823874/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1823874/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1516600/ |
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
Dose | Population | Adverse 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) Sources: Fatigue (1 patient) Chest pain (1 patient) |
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) Sources: Nausea (1 patient) Abdominal pain (1 patient) |
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 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9044164
Inhibitory constant of ambenonium to bovine erythrocyte AChE determined in vitro was 3.7 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:14:50 UTC 2023
by
admin
on
Fri Dec 15 15:14:50 UTC 2023
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Record UNII |
51FOB87G3I
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47792
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D000549
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CHEMBL1652
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AMBENONIUM CHLORIDE
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DTXSID3022582
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624
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115-79-7
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51FOB87G3I
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204-107-5
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100000087666
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C47388
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8288
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m1643
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DBSALT001309
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SUB05394MIG
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2628
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552
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |