General Information of Drug (ID: DM8HO1L)

Drug Name
Pyridostigmine
Synonyms
Pyridostigminum; Pyridostigmine Bromine; Mestinon (TN); Mestinon-SR; Regonol (TN); AQ-776/42801589; Pyridinium, 3-hydroxy-1-methyl-, dimethylcarbamate (ester); Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-(9CI); (1-methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate; 1-methyl-3-pyridiniumyl dimethylcarbamate; 3-(((Dimethylamino)carbonyl)oxy)-1-methylpyridinium
Indication
Disease Entry ICD 11 Status REF
Myasthenia gravis 8C6Y Approved [1]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 2/3 [2]
Therapeutic Class
Parasympathomimetics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 181.21
Logarithm of the Partition Coefficient (xlogp) 0.7
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 9.6 mL/min/kg [4]
Elimination
85% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.5 hours [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 76.59314 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 100 mg/mL [3]
Chemical Identifiers
Formula
C9H13N2O2+
IUPAC Name
(1-methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate
Canonical SMILES
C[N+]1=CC=CC(=C1)OC(=O)N(C)C
InChI
InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
InChIKey
RVOLLAQWKVFTGE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4991
ChEBI ID
CHEBI:8665
CAS Number
155-97-5
DrugBank ID
DB00545
TTD ID
D0O2WB
ACDINA ID
D00571
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Myasthenia gravis
ICD Disease Classification 8C6Y
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Pyridostigmine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Neostigmine DM6T2J3 Moderate Additive cholinergic effects by the combination of Pyridostigmine and Neostigmine. Myasthenia gravis [8C6Y] [7]
Edrophonium DMCRQHB Moderate Additive cholinergic effects by the combination of Pyridostigmine and Edrophonium. Myasthenia gravis [8C6Y] [7]
Coadministration of a Drug Treating the Disease Different from Pyridostigmine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Bethanechol DMCLHO0 Moderate Additive cholinergic effects by the combination of Pyridostigmine and Bethanechol. Abnormal micturition [MF50] [7]
Scopolamine DMOM8AL Moderate Antagonize the effect of Pyridostigmine when combined with Scopolamine. Addictive disorder [6C50-6C5Z] [8]
Framycetin DMF8DNE Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Framycetin. Alcoholic liver disease [DB94] [9]
Rivastigmine DMG629M Moderate Additive cholinergic effects by the combination of Pyridostigmine and Rivastigmine. Alzheimer disease [8A20] [7]
Donepezil DMIYG7Z Moderate Additive cholinergic effects by the combination of Pyridostigmine and Donepezil. Alzheimer disease [8A20] [7]
Paromomycin DM1AGXN Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Paromomycin. Amoebiasis [1A36] [9]
Kanamycin DM2DMPO Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Kanamycin. Bacterial infection [1A00-1C4Z] [9]
Streptomycin DME1LQN Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Streptomycin. Bacterial infection [1A00-1C4Z] [9]
Gentamicin DMKINJO Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Gentamicin. Bacterial infection [1A00-1C4Z] [9]
Netilmicin DMRD1QK Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Netilmicin. Bacterial infection [1A00-1C4Z] [9]
Tobramycin DMUI0CH Moderate Additive neuromuscular blocking effects by the combination of Pyridostigmine and Tobramycin. Bacterial infection [1A00-1C4Z] [9]
Mepenzolate DM8YU2F Moderate Antagonize the effect of Pyridostigmine when combined with Mepenzolate. Digestive system disease [DE2Z] [8]
Oxybutynine DMJPBAX Moderate Antagonize the effect of Pyridostigmine when combined with Oxybutynine. Discovery agent [N.A.] [8]
Solifenacin DMG592Q Moderate Antagonize the effect of Pyridostigmine when combined with Solifenacin. Functional bladder disorder [GC50] [8]
Tolterodine DMSHPW8 Moderate Antagonize the effect of Pyridostigmine when combined with Tolterodine. Functional bladder disorder [GC50] [8]
Clidinium DMUMQZ0 Moderate Antagonize the effect of Pyridostigmine when combined with Clidinium. Irritable bowel syndrome [DD91] [8]
Thalidomide DM70BU5 Moderate Increased risk of ventricular arrhythmias by the combination of Pyridostigmine and Thalidomide. Multiple myeloma [2A83] [10]
Fingolimod DM5JVAN Moderate Increased risk of atrioventricular block by the combination of Pyridostigmine and Fingolimod. Multiple sclerosis [8A40] [11]
Ozanimod DMT6AM2 Moderate Increased risk of atrioventricular block by the combination of Pyridostigmine and Ozanimod. Multiple sclerosis [8A40] [12]
Flavoxate DMKV4NL Moderate Antagonize the effect of Pyridostigmine when combined with Flavoxate. Pain [MG30-MG3Z] [8]
Biperiden DME78OA Moderate Antagonize the effect of Pyridostigmine when combined with Biperiden. Parkinsonism [8A00] [8]
Procainamide DMNMXR8 Moderate Antagonize the effect of Pyridostigmine when combined with Procainamide. Ventricular tachyarrhythmia [BC71] [8]
⏷ Show the Full List of 22 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Calcium phosphate E00298 24456 Anticaking agent; Buffering agent; Desiccant; Diluent
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Pyridostigmine 60 mg tablet 60 mg Oral Tablet Oral
Pyridostigmine 180 mg tablet 180 mg Extended Release Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040457.
2 ClinicalTrials.gov (NCT04343963) Pyridostigmine in Severe SARS-CoV-2 Infection. U.S. National Institutes of Health.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Neuromuscular blockade, reversal agent use, and operating room time: retrospective analysis of US inpatient surgeries. Curr Med Res Opin. 2009 Apr;25(4):943-50.
7 Product Information. Aricept (donepezil). Pfizer US Pharmaceuticals, New York, NY.
8 Product Information. Mestinon (pyridostigmine). ICN Pharmaceuticals Inc, Cost Mesa, CA.
9 Burkett L, Bikhazi GB, Thomas KC Jr, Rosenthal DA, Wirta MG, Foldes FF "Mutual potentiation of the neuromuscular effects of antibiotics and relaxants." Anesth Analg 58 (1979): 107-15. [PMID: 571233]
10 Cerner Multum, Inc. "Australian Product Information.".
11 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
12 Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.