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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

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MESTINON

Cmax

ValueDoseCo-administeredAnalytePopulation
176.03 ng/mL
60 mg single, oral
PYRIDOSTIGMINE BROMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
819.999 ng × h/mL
60 mg single, oral
PYRIDOSTIGMINE BROMIDE plasma
Homo sapiens
909.86 ng × h/mL
60 mg single, oral
PYRIDOSTIGMINE BROMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.787 h
60 mg single, oral
PYRIDOSTIGMINE BROMIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
18.8%
single, unknown
PYRIDOSTIGMINE BROMIDE unknown
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
Unknown