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

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
Structure of PYRIDOSTIGMINE

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

HIDE SMILES / InChI

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

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
In myasthenia gravis, clinical and immunological improvement post-thymectomy segregate with results of in vitro antibody secretion by immunocytes.
2002-10-15
Idiotypic mimicry of a catalytic antibody active site.
2002-10
Gulf War related exposure factors influencing topical absorption of 14C-permethrin.
2002-09-05
Acute and repeated restraint stress have little effect on pyridostigmine toxicity or brain regional cholinesterase inhibition in rats.
2002-09
Complete inhibition of hypothalamic somatostatin activity is only partially responsible for the growth hormone response to strenuous exercise.
2002-09
Pharmacokinetic/pharmacodynamic modeling of rocuronium in myasthenic patients is improved by taking into account the number of unbound acetylcholine receptors.
2002-09
Preparation and in vitro evaluation of pyridostigmine bromide microparticles.
2002-08-21
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.
2002-08-15
Cardiorespiratory effects following acute exposure to pyridostigmine bromide and/or N,N-diethyl-m-toluamide (DEET) in rats.
2002-08-13
Myasthenia gravis in pregnancy: report on 69 cases.
2002-08-05
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.
2002-08
Altered hypothalamic cholinergic responses in patients with nonulcer dyspepsia: a study of pyridostigmine-stimulated growth hormone release.
2002-08
Pharmacological antagonism of lethal effects induced by O-isobutyl S-[2-(diethylamino)ethyl]methylphosphonothioate.
2002-08
Subchronic administration of pyridostigmine or huperzine to primates: compared efficacy against soman toxicity.
2002-08
Locomotor and sensorimotor performance deficit in rats following exposure to pyridostigmine bromide, DEET, and permethrin. Alone and in combination.
2002-08
[Myasthenia gravis in infancy. A report of 12 cases].
2002-07-23
Neither forced running nor forced swimming affect acute pyridostigmine toxicity or brain-regional cholinesterase inhibition in rats.
2002-07-01
Use of intravenous pulsed cyclophosphamide in severe, generalized myasthenia gravis.
2002-07
Physiological and performance effects of pyridostigmine bromide in healthy volunteers: a dose-response study.
2002-07
Sensitivity to vecuronium in seropositive and seronegative patients with myasthenia gravis.
2002-07
Pyridostigmine bromide modulates the dermal disposition of [14C]permethrin.
2002-06-15
Pyridostigmine bromide and the long-term subjective health status of a sample of over 700 male Reserve Component Gulf War era veterans.
2002-06
Cholinergic stimulation with pyridostigmine reduces the QTc interval in coronary artery disease.
2002-06
[Growth disorders in Down's syndrome: growth hormone treatment].
2002-06
Caramiphen and scopolamine prevent soman-induced brain damage and cognitive dysfunction.
2002-05
Review of the value of huperzine as pretreatment of organophosphate poisoning.
2002-05
Impaired growth hormone secretion in fibromyalgia patients: evidence for augmented hypothalamic somatostatin tone.
2002-05
Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin.
2002-05
Actions of pyridostigmine and organophosphate agents on chick cells, mice, and chickens.
2002-05
Indirect evidence for decreased hypothalamic somatostatinergic tone in anorexia nervosa.
2002-03
Risk factors for multisymptom illness in US Army veterans of the Gulf War.
2002-03
Sensorimotor deficit and cholinergic changes following coexposure with pyridostigmine bromide and sarin in rats.
2002-03
In vitro human metabolism and interactions of repellent N,N-diethyl-m-toluamide.
2002-03
Ocular myasthenia presenting as progressive external ophthalmoplegia.
2002-02-28
Pyridophens: binary pyridostigmine-aprophen prodrugs with differential inhibition of acetylcholinesterase, butyrylcholinesterase, and muscarinic receptors.
2002-02-14
Peri-operative management of patients for video assisted thoracoscopic thymectomy in myasthenia gravis.
2002-02-08
Poor ovarian response to gonadotrophin stimulation the role of adjuvant treatments.
2002-02
The Department of Defense's Persian Gulf War registry year 2000: an examination of veterans' health status.
2002-02
B Cell lymphoma of the brain stem masquerading as myasthenia.
2002-02
Peripheral cholinergic pathway modulates hyperthermia induced by stress in rats exposed to open-field stress.
2002-02
Prevention and treatment of injury from chemical warfare agents.
2002-01-07
Major review: the clinical spectrum of pediatric myasthenia gravis: blepharoptosis, ophthalmoplegia and strabismus. A report of 14 cases.
2002
Bretazenil, a benzodiazepine receptor partial agonist, as an adjunct in the prophylactic treatment of OP poisoning.
2001-12
Intramuscular diazepam pharmacokinetics in soman-exposed guinea pigs.
2001-12
Beneficial effects of TCP on soman intoxication in guinea pigs: seizures, brain damage and learning behaviour.
2001-12
Combination anticonvulsant treatment of soman-induced seizures.
2001-12
Insulin-like growth factor-I restores the reduced somatostatinergic tone controlling growth hormone secretion in cirrhotic rats.
2001-12
The effect of continuous pyridostigmine administration on functional (A12) acetylcholinesterase activity in guinea-pig muscles.
2001-12
Laryngeal myasthenia gravis: report of 40 cases.
2001-03
Central nervous system effects from a peripherally acting cholinesterase inhibiting agent: interaction with stress or genetics.
2001-03
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:12:37 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:37 GMT 2025
Record UNII
19QM69HH21
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRIDOSTIGMINE
VANDF   WHO-DD  
Common Name English
PYRIDOSTIGMINE ION
Preferred Name English
Pyridostigmine [WHO-DD]
Common Name English
3-((DIMETHYLCARBAMOYL)OXY)-1-METHYLPYRIDINIUM
Systematic Name English
PYRIDINIUM, 3-(((DIMETHYLAMINO)CARBONYL)OXY)-1-METHYL-
Systematic Name English
PYRIDOSTIGMINE CATION
Common Name English
PYRIDOSTIGMINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC N07AA02
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 20
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
WHO-VATC QN07AA02
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
NDF-RT N0000175723
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
LIVERTOX 818
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
NCI_THESAURUS C47792
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
NDF-RT N0000000177
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
Code System Code Type Description
CAS
155-97-5
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
LACTMED
Pyridostigmine
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
DRUG BANK
DB00545
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID20165786
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
WIKIPEDIA
PYRIDOSTIGMINE
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
SMS_ID
100000078912
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
NCI_THESAURUS
C76139
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
PUBCHEM
4991
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
FDA UNII
19QM69HH21
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
EVMPD
SUB15059MIG
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
DRUG CENTRAL
2330
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
DAILYMED
19QM69HH21
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY
RXCUI
9000
Created by admin on Mon Mar 31 18:12:37 GMT 2025 , Edited by admin on Mon Mar 31 18:12:37 GMT 2025
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC