Details of the Drug

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]
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Therapeutic Class

Parasympathomimetics

Affected Organisms

Humans and other mammals

ATC Code

N07AA02: Pyridostigmine

N07AA: Anticholinesterases

N07A: PARASYMPATHOMIMETICS

N07: OTHER NERVOUS SYSTEM DRUGS

N: NERVOUS SYSTEM

N07AA02: Pyridostigmine

N07AA: Anticholinesterases

N07A: PARASYMPATHOMIMETICS

N07: OTHER NERVOUS SYSTEM DRUGS

N: NERVOUS SYSTEM

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
UNII: 19QM69HH21
DrugBank ID: DB00545
TTD ID: D0O2WB
ACDINA ID: D00571

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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]
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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]
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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
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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

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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.