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Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N2O2.Br
Molecular Weight 261.116
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRIDOSTIGMINE BROMIDE

SMILES

[Br-].CN(C)C(=O)OC1=C[N+](C)=CC=C1

InChI

InChIKey=VNYBTNPBYXSMOO-UHFFFAOYSA-M
InChI=1S/C9H13N2O2.BrH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1

HIDE SMILES / InChI

Description
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.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MESTINON

Approved Use

Pyridostigmine bromide is useful in the treatment of myasthenia gravis.

Launch Date

1955
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
18.8%
single, unknown
PYRIDOSTIGMINE BROMIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Prognostic factors of thymectomy in patients with myasthenia gravis: a cohort of 132 patients.
2001
Combined exposure to sarin and pyridostigmine bromide increased levels of rat urinary 3-nitrotyrosine and 8-hydroxy-2'-deoxyguanosine, biomarkers of oxidative stress.
2001 Aug 6
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
Effects of contralateral white noise stimulation on distortion product otoacoustic emissions in myasthenic patients.
2001 Dec
A validated HPLC method for the determination of pyridostigmine bromide, acetaminophen, acetylsalicylic acid and caffeine in rat plasma and urine.
2001 Dec
Enhancement of heart rate variability by cholinergic stimulation with pyridostigmine in healthy subjects.
2001 Feb
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
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
The use of carbamates, atropine, and 2-pyridine aldoxime methoiodide in the protection of Artemia salina against poisoning by carbophenothion.
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
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
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
Patents

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
Name Type Language
KALIMIN
Preferred Name English
PYRIDOSTIGMINE BROMIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
RO-1-5130
Code English
PYRIDOSTIGMINE BROMIDE [MI]
Common Name English
KALYMIN
Brand Name English
PYRIDINIUM, 3-(((DIMETHYLAMINO)CARBONYL)OXY)-1-METHYL-, BROMIDE (1:1)
Systematic Name English
PYRIDOSTIGMINE BROMIDE [ORANGE BOOK]
Common Name English
NSC-679759
Code English
PYRIDOSTIGMINI BROMIDUM [WHO-IP LATIN]
Common Name English
PYRIDOSTIGMINE BROMIDE [JAN]
Common Name English
REGONOL
Brand Name English
PYRIDOSTIGMINE BROMIDE [MART.]
Common Name English
PYRIDOSTIGMINE BROMIDE [EP IMPURITY]
Common Name English
3-Hydroxy-1-methylpyridinium bromide dimethylcarbamate
Systematic Name English
Pyridostigmine bromide [WHO-DD]
Common Name English
PYRIDOSTIGMINE BROMIDE [EP MONOGRAPH]
Common Name English
NSC-758435
Code English
PYRIDOSTIGMINE BROMIDE [WHO-IP]
Common Name English
MESTINON
Brand Name English
PYRIDINIUM, 3-(((DIMETHYLAMINO)CARBONYL)OXY)-1-METHYL-, BROMIDE
Systematic Name English
PYRIDOSTIGMINE BROMIDE [HSDB]
Common Name English
PYRIDOSTIGMINE BROMIDE [USP MONOGRAPH]
Common Name English
PYRIDOSTIGMINE BROMIDE [USP-RS]
Common Name English
pyridostigmine bromide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
EPA PESTICIDE CODE 227702
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
Code System Code Type Description
DRUG BANK
DBSALT000190
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
NCI_THESAURUS
C47697
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
FDA UNII
KVI301NA53
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
NSC
679759
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PYRIDOSTIGMINE BROMIDE
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY Description: A white or almost white, crystalline powder; odour, agreeable, characteristic. Solubility: Soluble in less than 1 part of water and ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Cholinergic. Storage: Pyridostigmine bromide should be kept in a well-closed container, protected from light. Additional information: Pyridostigmine bromide is deliquescent.Definition: Pyridostigmine bromide contains not less than 98.5% and not more than 101.0% of C9H13BrN2O2, calculated with reference to the dried substance.
MERCK INDEX
m9360
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY Merck Index
HSDB
3924
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-929-9
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID9023540
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
RXCUI
9001
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY RxNorm
PUBCHEM
7550
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
RS_ITEM_NUM
1586009
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
SMS_ID
100000091854
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
ChEMBL
CHEMBL1115
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
EVMPD
SUB10167MIG
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
INN
278
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
DAILYMED
KVI301NA53
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
NSC
758435
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
MESH
D011729
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY
CAS
101-26-8
Created by admin on Wed Apr 02 07:02:34 GMT 2025 , Edited by admin on Wed Apr 02 07:02:34 GMT 2025
PRIMARY