Pyridostigmine chlorideProduct ingredient for Pyridostigmine

Name
Pyridostigmine chloride
Drug Entry
Pyridostigmine

Myasthenia gravis is an autoimmune disease involving dysfunction at the neuromuscular junction, most commonly due to autoantibodies directed against the acetylcholine receptor (AChR), which results in muscle tone loss, muscle weakness, and fatigue.2 Acetylcholinesterase inhibitors have been the symptomatic treatment of choice in myasthenia gravis since the 1930s with the early use of physostigmine and neostigmine. By inhibiting the breakdown of acetylcholine in the neuromuscular junction, they increase signalling and relieve symptoms.2,10,11 Pyridostigmine is the current drug of choice, with superior pharmacokinetics and reduced side effects compared to neostigmine.10,11 In addition to treating myasthenia gravis, pyridostigmine is used to reverse neuromuscular blocks, relieve symptoms in congenital myasthenic syndromes, and protect against certain nerve agents, notably during the Gulf War.3,4,11,12

Pyridostigmine was granted initial FDA approval on April 6, 1955, as an oral tablet. Possible dose forms have been expanded to include extended-release tablets, syrups, and injections, marketed under various brand and generic names.10,11

Accession Number
DBSALT002338
Structure
Synonyms
Not Available
UNII
45X1P9AO69
CAS Number
7681-22-3
Weight
Average: 216.67
Monoisotopic: 216.0665554
Chemical Formula
C9H13ClN2O2
InChI Key
TYXYRYORUZYJDX-UHFFFAOYSA-M
InChI
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
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium chloride
SMILES
[Cl-].CN(C)C(=O)OC1=C[N+](C)=CC=C1
ChemSpider
175091
Predicted Properties
PropertyValueSource
Water Solubility1.71 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.5Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)19.53Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area33.42 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity49.66 m3·mol-1Chemaxon
Polarizability19.37 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon