Pyridostigmine

Identification

Name
Pyridostigmine
Accession Number
DB00545
Description

A cholinesterase inhibitor with a slightly longer duration of action than neostigmine. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 181.2117
Monoisotopic: 181.09770267
Chemical Formula
C9H13N2O2
Synonyms
  • Piridostigmina
  • Pyridostigmine cation

Pharmacology

Indication

For the treatment of myasthenia gravis.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Pyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. Since it is a quaternary amine, it is poorly absorbed in the gut and doesn't cross the blood-brain barrier. Pyridostigmine has a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.

Mechanism of action

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 prolonges the effects of acetylcholine.

TargetActionsOrganism
AAcetylcholinesterase
antagonist
inhibitor
Humans
ACholinesterase
antagonist
Humans
USerum albuminNot AvailableHumans
Absorption

Poorly absorbed from the GI tract with an oral bioavailability of 7.6 +/- 2.4%.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hydrolysis by cholinesterases and by liver.

Route of elimination
Not Available
Half-life

3 hours following oral administration.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololPyridostigmine may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Acetylcholine.
AclidiniumPyridostigmine may increase the neuromuscular blocking activities of Aclidinium.
AmantadineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Pyridostigmine.
AmifampridineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Amifampridine.
AmitriptylineThe therapeutic efficacy of Amitriptyline can be decreased when used in combination with Pyridostigmine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Pyridostigmine.
AmoxapineThe therapeutic efficacy of Amoxapine can be decreased when used in combination with Pyridostigmine.
Anisotropine methylbromideThe therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Pyridostigmine.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Pyridostigmine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food. Food decreases irritation.

Products

Product Ingredients
IngredientUNIICASInChI Key
Pyridostigmine bromideKVI301NA53101-26-8VNYBTNPBYXSMOO-UHFFFAOYSA-M
Pyridostigmine chloride45X1P9AO697681-22-3TYXYRYORUZYJDX-UHFFFAOYSA-M
Product Images
International/Other Brands
Amiasten (AC Farma) / Amygra (Tabros) / Antilon (Yuan Chou) / Astinon (Samarth) / Kalymin (Arzneimittelwerk Dresden) / Kalymin forte (Temmler) / Kalymin N (Temmler) / Kalymin retard (Temmler) / Meshanon60 (Hasan) / Mestinon retard (Meda) / Myestin (VHB) / Pyrimine (Sriprasit Dispensary)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MestinonTablet, extended release180 mg/1OralBausch Health US, LLC1959-01-12Not applicableUS flag
MestinonTablet60 mg/1OralBausch Health US, LLC1955-04-06Not applicableUS flag
MestinonTablet60 mgOralBausch Health, Canada Inc.1990-12-31Not applicableCanada flag
MestinonSolution60 mg/5mLOralBausch Health US, LLC1965-01-25Not applicableUS flag
Mestinon-SRTablet, extended releaseOralBausch Health, Canada Inc.1991-12-31Not applicableCanada flag
Pyridostigmine BromideTablet30 mg/1OralSurgeon General-Department of the Army (TSG-DA)1990-12-05Not applicableUS flag
Pyridostigmine bromideTablet30 mg/1OralValeant Pharmaceuticals2008-10-27Not applicableUS flag
RegonolInjection, solution5 mg/1mLIntravenous; ParenteralSandoz Inc2005-05-10Not applicableUS flag
Regonol Inj 5mg/mlLiquidIntramuscular; IntravenousOrganon Canada Ltd Ltee1977-12-311999-08-11Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Pryidostigmine BromideSolution60 mg/5mLOralTrigen Laboratories LLC2020-01-30Not applicableUS flag
PyridostigmineSolution60 mg/5mLOralNovitium Pharma Llc2019-03-11Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralEywa Pharma Inc2019-04-17Not applicableUS flag
Pyridostigmine BromideTablet, extended release180 mg/1OralNucare Pharmaceuticals,inc.2015-09-18Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralCadila Healthcare Limited2015-08-07Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralRemedy Repack2011-10-042012-10-04US flag00115 3511 01 nlmimage10 c60e6313
Pyridostigmine BromideTablet60 mg/1OralMcKesson Corporation dba RX Pak2019-04-17Not applicableUS flag
Pyridostigmine BromideTablet, extended release180 mg/1OralAmneal Pharmaceuticals of New York Llc2015-09-18Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralOceanside Pharmaceuticals2007-10-30Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralZydus Pharmaceuticals (USA) Inc.2015-08-07Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
N07AA02 — Pyridostigmine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-methylpyridinium compounds. These are methylpyridines that carry a methyl group at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Methylpyridines
Direct Parent
N-methylpyridinium compounds
Alternative Parents
Pyridinium derivatives / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / N-methylpyridinium / Organic cation / Organic nitrogen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:8665)

Chemical Identifiers

UNII
19QM69HH21
CAS number
155-97-5
InChI Key
RVOLLAQWKVFTGE-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium
SMILES
CN(C)C(=O)OC1=C[N+](C)=CC=C1

References

Synthesis Reference

Thomas Zich, "Preparation of substituted pyridine N-oxide compounds." U.S. Patent US20040063957, issued April 01, 2004.

US20040063957
General References
  1. Singer W, Opfer-Gehrking TL, McPhee BR, Hilz MJ, Bharucha AE, Low PA: Acetylcholinesterase inhibition: a novel approach in the treatment of neurogenic orthostatic hypotension. J Neurol Neurosurg Psychiatry. 2003 Sep;74(9):1294-8. [PubMed:12933939]
Human Metabolome Database
HMDB0014685
KEGG Drug
D00487
KEGG Compound
C07410
PubChem Compound
4991
PubChem Substance
46506129
ChemSpider
4817
BindingDB
50313079
RxNav
9000
ChEBI
8665
ChEMBL
CHEMBL1115
ZINC
ZINC000000002009
Therapeutic Targets Database
DNC001171
PharmGKB
PA451185
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pyridostigmine
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
FDA label
Download (120 KB)
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentOrthostatic; Hypotension, Neurogenic1
4CompletedTreatmentPostural Orthostatic Tachycardia Syndrome (POTS)1
4RecruitingTreatmentMyasthenia Gravis1
4Unknown StatusSupportive CareMuscle Relaxation1
3CompletedTreatmentLeukemias1
3TerminatedTreatmentOcular Myasthenia Gravis1
2CompletedOtherHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentFibromyalgia1
2CompletedTreatmentHeart Failure1
2CompletedTreatmentKugelberg-Welander Disease / SMA / Spinal Muscular Atrophy (SMA)1

Pharmacoeconomics

Manufacturers
  • Valeant pharmaceuticals international
  • Sandoz canada inc
  • Barr laboratories inc
  • Corepharma llc
  • Impax laboratories inc
  • Solvay pharmaceuticals
  • United states army office surgeon general
Packagers
  • Barr Pharmaceuticals
  • Corepharma LLC
  • DSM Corp.
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Kaiser Foundation Hospital
  • Legacy Pharmaceuticals Packaging LLC
  • Murfreesboro Pharmaceutical Nursing Supply
  • Oceanside Pharmaceuticals Incorporated
  • Professional Co.
  • Sandoz
  • Southcoast Pharmaceuticals Inc.
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
Tablet, coatedOral500 mg
Tablet, coatedOral60 mg
TabletOral60 mg
Tablet60 MG
Tablet, extended releaseOral180 MG
Tablet, film coated60 mg
Tablet
Tablet, extended releaseOral
SolutionOral60 mg/5mL
TabletOral180 mg/1
TabletOral30 mg/1
TabletOral60 mg/1
Tablet, extended releaseOral180 mg/1
Injection, solutionIntravenous; Parenteral5 mg/1mL
LiquidIntramuscular; Intravenous
TabletOral
Prices
Unit descriptionCostUnit
Mestinon 30 180 mg Controlled Release Tabs Bottle129.42USD bottle
Pyridostigmine bromide powder87.6USD g
Regonol 5 mg/ml ampul13.64USD ml
Mestinon 180 mg timespan3.59USD each
Mestinon 60 mg tablet2.46USD tablet
Mestinon-Sr 180 mg Sustained-Release Tablet1.06USD tablet
Pyridostigmine Bromide 60 mg tablet0.62USD tablet
Pyridostigmine br 60 mg tablet0.6USD tablet
Mestinon 60 mg Tablet0.48USD tablet
Mestinon 60 mg/5ml Syrup0.43USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)153 °CNot Available
logP1.554Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.5ChemAxon
logS-2.3ALOGPS
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
Polarizability19.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9441
Blood Brain Barrier+0.9818
Caco-2 permeable+0.6465
P-glycoprotein substrateNon-substrate0.737
P-glycoprotein inhibitor INon-inhibitor0.915
P-glycoprotein inhibitor IINon-inhibitor0.8654
Renal organic cation transporterNon-inhibitor0.8863
CYP450 2C9 substrateNon-substrate0.7541
CYP450 2D6 substrateNon-substrate0.7082
CYP450 3A4 substrateSubstrate0.586
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.9274
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9782
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8422
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9193
BiodegradationReady biodegradable0.5528
Rat acute toxicity3.1468 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9248
hERG inhibition (predictor II)Non-inhibitor0.8484
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Drake-Baumann R, Seil FJ: Effects of exposure to low-dose pyridostigmine on neuromuscular junctions in vitro. Muscle Nerve. 1999 Jun;22(6):696-703. [PubMed:10366222]
  2. Ricordel I, Meunier J: [Chemical weapons: antidotes. View about the real means, perspectives]. Ann Pharm Fr. 2000 Jan;58(1):5-12. [PubMed:10669805]
  3. Prasad V, Scotch R, Chaudhuri AR, Walss C, Fathy DB, Miller C, Luduena RF: Interactions of bovine brain tubulin with pyridostigmine bromide and N,N'-diethyl-m-toluamide. Neurochem Res. 2000 Jan;25(1):19-25. [PubMed:10685600]
  4. Sinton CM, Fitch TE, Petty F, Haley RW: Stressful manipulations that elevate corticosterone reduce blood-brain barrier permeability to pyridostigmine in the Rat. Toxicol Appl Pharmacol. 2000 May 15;165(1):99-105. [PubMed:10814558]
  5. Servatius RJ, Ottenweller JE, Guo W, Beldowicz D, Zhu G, Natelson BH: Effects of inescapable stress and treatment with pyridostigmine bromide on plasma butyrylcholinesterase and the acoustic startle response in rats. Physiol Behav. 2000 May;69(3):239-46. [PubMed:10869589]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Somani SM, Husain K, Asha T, Helfert R: Interactive and delayed effects of pyridostigmine and physical stress on biochemical and histological changes in peripheral tissues of mice. J Appl Toxicol. 2000 Jul-Aug;20(4):327-34. [PubMed:10942908]
  2. Servatius RJ, Ottenweller JE, Guo W, Beldowicz D, Zhu G, Natelson BH: Effects of inescapable stress and treatment with pyridostigmine bromide on plasma butyrylcholinesterase and the acoustic startle response in rats. Physiol Behav. 2000 May;69(3):239-46. [PubMed:10869589]
  3. Abou-Donia MB, Wilmarth KR, Abdel-Rahman AA, Jensen KF, Oehme FW, Kurt TL: Increased neurotoxicity following concurrent exposure to pyridostigmine bromide, DEET, and chlorpyrifos. Fundam Appl Toxicol. 1996 Dec;34(2):201-22. [PubMed:8954750]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Abu-Qare AW, Abou-Donia MB: Binding of pyridostigmine bromide, N,N-diethyl-m-toluamide and permethrin, alone and in combinations, to human serum albumin. Arch Toxicol. 2002 May;76(4):203-8. Epub 2002 Mar 9. [PubMed:12029383]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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