Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H13N2O2.Cl |
| Molecular Weight | 216.665 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CN(C)C(=O)OC1=C[N+](C)=CC=C1
InChI
InChIKey=TYXYRYORUZYJDX-UHFFFAOYSA-M
InChI=1S/C9H13N2O2.ClH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1
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
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 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
180 mg 3 times / day multiple, oral MTD Dose: 180 mg, 3 times / day Route: oral Route: multiple Dose: 180 mg, 3 times / day Sources: |
unhealthy, 18-67 years n = 10 Health Status: unhealthy Condition: autonomic neuropathy | constipation Age Group: 18-67 years Sex: M+F Population Size: 10 Sources: |
|
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: |
unhealthy, 18-67 years n = 10 Health Status: unhealthy Condition: autonomic neuropathy | constipation Age Group: 18-67 years Sex: M+F Population Size: 10 Sources: |
DLT: Diaphoresis, Sweating... Dose limiting toxicities: Diaphoresis (10%) Sources: Sweating (10%) Abdominal cramps (10%) |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
Disc. AE: Headache, Hypertension... AEs leading to discontinuation/dose reduction: Headache (0.002%) Sources: Hypertension (0.005%) Allergic reaction (0.005%) Bronchitis (0.007%) Nausea (0.05%) Diarrhea (0.05%) |
900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
Other AEs: Abdominal cramps, Diarrhea... Other AEs: Abdominal cramps Sources: Diarrhea Emesis Nausea Hypersalivation Urinary incontinence Muscle weakness Blurred vision |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abdominal cramps | 10% DLT |
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: |
unhealthy, 18-67 years n = 10 Health Status: unhealthy Condition: autonomic neuropathy | constipation Age Group: 18-67 years Sex: M+F Population Size: 10 Sources: |
| Diaphoresis | 10% DLT |
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: |
unhealthy, 18-67 years n = 10 Health Status: unhealthy Condition: autonomic neuropathy | constipation Age Group: 18-67 years Sex: M+F Population Size: 10 Sources: |
| Sweating | 10% DLT |
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: |
unhealthy, 18-67 years n = 10 Health Status: unhealthy Condition: autonomic neuropathy | constipation Age Group: 18-67 years Sex: M+F Population Size: 10 Sources: |
| Headache | 0.002% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Allergic reaction | 0.005% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Hypertension | 0.005% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Bronchitis | 0.007% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Diarrhea | 0.05% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Nausea | 0.05% Disc. AE |
30 mg 3 times / day multiple, oral Recommended Dose: 30 mg, 3 times / day Route: oral Route: multiple Dose: 30 mg, 3 times / day Sources: |
healthy, adult n = 41650 Health Status: healthy Age Group: adult Sex: M+F Population Size: 41650 Sources: |
| Abdominal cramps | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Blurred vision | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Diarrhea | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Emesis | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Hypersalivation | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Muscle weakness | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Nausea | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
|
| Urinary incontinence | 900 mg 1 times / day single, oral Studied dose Dose: 900 mg, 1 times / day Route: oral Route: single Dose: 900 mg, 1 times / day Sources: |
healthy, adult n = 1 Health Status: healthy Age Group: adult Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Prognostic factors of thymectomy in patients with myasthenia gravis: a cohort of 132 patients. | 2001 |
|
| Bretazenil, a benzodiazepine receptor partial agonist, as an adjunct in the prophylactic treatment of OP poisoning. | 2001 Dec |
|
| Intramuscular diazepam pharmacokinetics in soman-exposed guinea pigs. | 2001 Dec |
|
| Beneficial effects of TCP on soman intoxication in guinea pigs: seizures, brain damage and learning behaviour. | 2001 Dec |
|
| Combination anticonvulsant treatment of soman-induced seizures. | 2001 Dec |
|
| 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 |
|
| Laryngeal myasthenia gravis: report of 40 cases. | 2001 Mar |
|
| Central nervous system effects from a peripherally acting cholinesterase inhibiting agent: interaction with stress or genetics. | 2001 Mar |
|
| 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 |
|
| Peri-operative management of patients for video assisted thoracoscopic thymectomy in myasthenia gravis. | 2001 Oct-Dec |
|
| Minimal change nephrotic syndrome associated with malignant thymoma: case report and literature review. | 2001 Sep |
|
| Myasthenia gravis in children: analysis of 18 patients. | 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 |
|
| Altered hypothalamic cholinergic responses in patients with nonulcer dyspepsia: a study of pyridostigmine-stimulated growth hormone release. | 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 |
|
| Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin. Alone and in combination. | 2002 Aug |
|
| A comparison of the efficacy of pyridostigmine alone and the combination of pyridostigmine with anticholinergic drugs as pharmacological pretreatment of tabun-poisoned rats and mice. | 2002 Aug 15 |
|
| Preparation and in vitro evaluation of pyridostigmine bromide microparticles. | 2002 Aug 21 |
|
| Myasthenia gravis in pregnancy: report on 69 cases. | 2002 Aug 5 |
|
| The Department of Defense's Persian Gulf War registry year 2000: an examination of veterans' health status. | 2002 Feb |
|
| The use of the pyridostigmine growth hormone-releasing hormone stimulation test to detect growth hormone deficiency in patients with pituitary adenomas. | 2002 Jan |
|
| Presentation of myasthenia gravis mimicking blepharospasm. | 2002 Jan 8 |
|
| Ocular myasthenia presenting as progressive external ophthalmoplegia. | 2002 Jan-Feb |
|
| Use of intravenous pulsed cyclophosphamide in severe, generalized myasthenia gravis. | 2002 Jul |
|
| Physiological and performance effects of pyridostigmine bromide in healthy volunteers: a dose-response study. | 2002 Jul |
|
| Sensitivity to vecuronium in seropositive and seronegative patients with myasthenia gravis. | 2002 Jul |
|
| Neither forced running nor forced swimming affect acute pyridostigmine toxicity or brain-regional cholinesterase inhibition in rats. | 2002 Jul 1 |
|
| Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats. | 2002 Jul-Aug |
|
| Pyridostigmine bromide and the long-term subjective health status of a sample of over 700 male Reserve Component Gulf War era veterans. | 2002 Jun |
|
| Cholinergic stimulation with pyridostigmine reduces the QTc interval in coronary artery disease. | 2002 Jun |
|
| [Growth disorders in Down's syndrome: growth hormone treatment]. | 2002 Jun |
|
| Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin. | 2002 Jun 15 |
|
| Indirect evidence for decreased hypothalamic somatostatinergic tone in anorexia nervosa. | 2002 Mar |
|
| Sensorimotor deficit and cholinergic changes following coexposure with pyridostigmine bromide and sarin in rats. | 2002 Mar |
|
| Caramiphen and scopolamine prevent soman-induced brain damage and cognitive dysfunction. | 2002 May |
|
| Review of the value of huperzine as pretreatment of organophosphate poisoning. | 2002 May |
|
| Impaired growth hormone secretion in fibromyalgia patients: evidence for augmented hypothalamic somatostatin tone. | 2002 May |
|
| Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin. | 2002 May |
|
| Actions of pyridostigmine and organophosphate agents on chick cells, mice, and chickens. | 2002 May |
|
| [Myasthenia gravis in infancy. A report of 12 cases]. | 2002 May 16-31 |
|
| Idiotypic mimicry of a catalytic antibody active site. | 2002 Oct |
|
| In myasthenia gravis, clinical and immunological improvement post-thymectomy segregate with results of in vitro antibody secretion by immunocytes. | 2002 Oct 15 |
|
| Acute and repeated restraint stress have little effect on pyridostigmine toxicity or brain regional cholinesterase inhibition in rats. | 2002 Sep |
|
| Complete inhibition of hypothalamic somatostatin activity is only partially responsible for the growth hormone response to strenuous exercise. | 2002 Sep |
|
| Pharmacokinetic/pharmacodynamic modeling of rocuronium in myasthenic patients is improved by taking into account the number of unbound acetylcholine receptors. | 2002 Sep |
|
| Gulf War related exposure factors influencing topical absorption of 14C-permethrin. | 2002 Sep 5 |
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
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
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Common Name | English | ||
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Systematic Name | English |
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45X1P9AO69
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DTXSID90998129
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202190
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7681-22-3
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DBSALT002338
Created by
admin on Fri Dec 15 15:17:25 GMT 2023 , Edited by admin on Fri Dec 15 15:17:25 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
