Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H13N2O2 |
Molecular Weight | 181.2117 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)OC1=C[N+](C)=CC=C1
InChI
InChIKey=RVOLLAQWKVFTGE-UHFFFAOYSA-N
InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
Molecular Formula | C9H13N2O2 |
Molecular Weight | 181.2117 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21815707
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21815707
Acquired myasthenia gravis (MG) is a chronic autoimmune disorder of the neuromuscular junction, characterized clinically by muscle weakness and abnormal fatigability on exertion. Current guidelines and recommendations for MG treatment are based largely on clinical experience, retrospective analyses and expert consensus. Pyridostigmine (under the trade names Mestinon (Valeant Pharmaceuticals)), has been used as a treatment for MG for over 50 years and is generally considered safe. It is suitable as a long-term treatment in patients with generalized non-progressive milder disease, and as an adjunctive therapy in patients with severe disease who are also receiving immunotherapy. Pyridostigmine inhibits acetylcholinesterase in the synaptic cleft by competing with acetylcholine for attachment to acetylcholinesterase, thus slowing down the hydrolysis of acetylcholine, and thereby increases efficiency of cholinergic transmission in the neuromuscular junction and prolongs the effects of acetylcholine. The side effects of Mestinon are most commonly related to over dosage and generally are of two varieties, muscarinic and nicotinic. Among those in the former group are nausea, vomiting, diarrhea, abdominal cramps, increased peristalsis, increased salivation, increased bronchial secretions, miosis and diaphoresis. Nicotinic side effects are comprised chiefly of muscle cramps, fasciculation and weakness. Muscarinic side effects can usually be counteracted by atropine, but for reasons shown in the preceding section the expedient is not without danger. As with any compound containing the bromide radical, a skin rash may be seen in an occasional patient. Such reactions usually subside promptly upon discontinuance of the medication.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10814558 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MESTINON Approved UsePyridostigmine bromide is useful in the treatment of myasthenia gravis. Launch Date1955 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
176.03 ng/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PYRIDOSTIGMINE BROMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
819.999 ng × h/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PYRIDOSTIGMINE BROMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
909.86 ng × h/mL |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PYRIDOSTIGMINE BROMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.787 h |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PYRIDOSTIGMINE BROMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.8% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12029383 |
single, unknown |
PYRIDOSTIGMINE BROMIDE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12642463/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no |
PubMed
Title | Date | PubMed |
---|---|---|
Neurotoxicology of the brain barrier system: new implications. | 2001 |
|
[Myasthenia gravis associated with HIV infection]. | 2001 |
|
Familial autoimmune myasthenia gravis. | 2001 Apr |
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Exercise stress testing in healthy subjects during cholinergic stimulation after a single dose of pyridostigmine. | 2001 Apr |
|
Analysis of thymectomy for myasthenia gravis in older patients: a 20-year single institution experience. | 2001 Apr |
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Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin, alone and in combination. | 2001 Apr |
|
Side effects of low-dose pyridostigmine bromide are not related to cholinesterase inhibition. | 2001 Dec |
|
A validated HPLC method for the determination of pyridostigmine bromide, acetaminophen, acetylsalicylic acid and caffeine in rat plasma and urine. | 2001 Dec |
|
Perioperative management of a patient with congenital myasthenia gravis for elective caesarean section. | 2001 Feb |
|
Biological consequences of multiple vaccine and pyridostigmine pretreatment in the guinea pig. | 2001 Jan-Feb |
|
Myasthenia gravis during low-dose IFN-alpha therapy for chronic hepatitis C. | 2001 Jul |
|
Involvement of the cholinergic pathway in the pathogenesis of pituitary Cushing's syndrome. | 2001 Jun |
|
Subchronic administration of various pretreatments of nerve agent poisoning. I. Protection of blood and central cholinesterases, innocuousness towards blood-brain barrier permeability. | 2001 May |
|
Fetal antigen 1 in healthy adults and patients with pituitary disease: relation to physiological, pathological, and pharmacological GH levels. | 2001 Nov |
|
Reactive oxygen species mediate pyridostigmine-induced neuronal apoptosis: involvement of muscarinic and NMDA receptors. | 2001 Nov 15 |
|
Long-term evaluation of extended thymectomy with anterior mediastinal dissection for myasthenia gravis. | 2001 Oct |
|
The combined effects of pyridostigmine and chronic stress on brain cortical and blood acetylcholinesterase, corticosterone, prolactin and alternation performance in rats. | 2001 Oct-Nov |
|
Myasthenia gravis in children: analysis of 18 patients. | 2001 Sep |
|
Electroplegia: an alternative to blood cardioplegia for arresting the heart during conventional (on-pump) cardiac operation. | 2001 Sep |
|
Major review: the clinical spectrum of pediatric myasthenia gravis: blepharoptosis, ophthalmoplegia and strabismus. A report of 14 cases. | 2002 |
|
Disruption of the blood-brain barrier and neuronal cell death in cingulate cortex, dentate gyrus, thalamus, and hypothalamus in a rat model of Gulf-War syndrome. | 2002 Aug |
|
Pharmacological antagonism of lethal effects induced by O-isobutyl S-[2-(diethylamino)ethyl]methylphosphonothioate. | 2002 Aug |
|
Subchronic administration of pyridostigmine or huperzine to primates: compared efficacy against soman toxicity. | 2002 Aug |
|
B Cell lymphoma of the brain stem masquerading as myasthenia. | 2002 Feb |
|
Presentation of myasthenia gravis mimicking blepharospasm. | 2002 Jan 8 |
|
Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats. | 2002 Jul-Aug |
|
Cholinergic stimulation with pyridostigmine reduces the QTc interval in coronary artery disease. | 2002 Jun |
|
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin. | 2002 Jun 15 |
|
Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin. | 2002 May |
|
[Myasthenia gravis in infancy. A report of 12 cases]. | 2002 May 16-31 |
Sample Use Guides
Syrup: This form permits accurate dosage adjustment for children and "brittle" myasthenic patients who require fractions of 60 mg doses. It is more easily swallowed, especially in the morning, by patients with bulbar involvement.
Timespan Tablets: This form provides uniformly slow release, hence prolonged duration of drug action; it facilitates control of myasthenic symptoms with fewer individual doses daily. The immediate effect of a 180 mg Timespan Tablet is about equal to that of a 60 mg Conventional Tablet; however, its duration of effectiveness, although varying in individual patients, averages 2½ times that of a 60 mg dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19694313
Curator's Comment: The objective of this study was to investigate the effect of Mestinon (Pyridostigmin) on platelet aggregation stimulated with various agonists in vitro. The results showed that in the presence of pyridostigmine, platelet aggregation was inhibited in response to ADP and collagen stimulations. However, when agonists such as ristocetin and arachidonic acid were used, aggregation of platelets was detectable even though the degree of aggregation was relatively reduced when compared with control samples. Pyridostigmine interferes with human platelet aggregation and uncommonly in susceptible patient may result in bleeding tendency.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:12:37 GMT 2025
by
admin
on
Mon Mar 31 18:12:37 GMT 2025
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Record UNII |
19QM69HH21
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
N07AA02
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WHO-ESSENTIAL MEDICINES LIST |
20
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WHO-VATC |
QN07AA02
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NDF-RT |
N0000175723
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LIVERTOX |
818
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NCI_THESAURUS |
C47792
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NDF-RT |
N0000000177
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155-97-5
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Pyridostigmine
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DB00545
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DTXSID20165786
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PYRIDOSTIGMINE
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100000078912
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C76139
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4991
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19QM69HH21
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SUB15059MIG
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2330
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19QM69HH21
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9000
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Volume of Distribution | PHARMACOKINETIC |
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