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Identification
NamePyridostigmine
Accession NumberDB00545  (APRD00380)
TypeSmall Molecule
GroupsApproved
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. [PubChem]

Structure
Thumb
Synonyms
Bromure de Pyridostigmine
Bromuro de piridostigmina
Mestinon
Pyridostigmin bromid
Pyridostigmine
Pyridostigmini Bromidum
Regonol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mestinontablet60 mg/1oralValeant Pharmaceuticals North America LLC1955-04-06Not applicableUs
Mestinontablet, extended release180 mg/1oralValeant Pharmaceuticals North America LLC1959-01-12Not applicableUs
Mestinonsyrup60 mg/5mLoralValeant Pharmaceuticals North America LLC1965-01-25Not applicableUs
Mestinon Tab 60mg USPtablet60 mgoralValeant Canada Lp Valeant Canada S.E.C.1990-12-31Not applicableCanada
Mestinon-SRtablet (extended-release)180 mgoralValeant Canada Lp Valeant Canada S.E.C.1991-12-31Not applicableCanada
Pyridostigmine Bromidetablet60 mg/1oralOceanside Pharmaceuticals2007-10-30Not applicableUs
Pyridostigmine Bromidetablet, extended release180 mg/1oralOceanside Pharmaceuticals1959-01-12Not applicableUs
Regonolinjection, solution5 mg/mLintravenous; parenteralSandoz Inc2005-05-10Not applicableUs
Regonol Inj 5mg/mlliquid5 mgintramuscular; intravenousOrganon Canada Ltd Ltee1977-12-311999-08-11Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pyridostigmine Bromidetablet, extended release180 mg/1oralImpax Generics2015-09-18Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralZydus Pharmaceuticals (USA) Inc.2015-08-07Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralAmerican Health Packaging2011-09-30Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralCadila Healthcare Limited2015-08-07Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralREMEDYREPACK INC.2011-10-04Not applicableUs
Pyridostigmine Bromidetablet, extended release180 mg/1oralAlvogen Inc.2015-06-29Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralKAISER FOUNDATION HOSPITALS2010-08-02Not applicableUs
Pyridostigmine Bromidetablet60 mg/1oralImpax Generics2003-04-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmiastenAC Farma
AmygraTabros
AntilonYuan Chou
AstinonSamarth
KalyminArzneimittelwerk Dresden
Kalymin forteTemmler
Kalymin NTemmler
Kalymin retardTemmler
Meshanon60Hasan
Mestinon retardMeda
MyestinVHB
PyrimineSriprasit Dispensary
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pyridostigmine Bromide
Thumb
  • InChI Key: VNYBTNPBYXSMOO-UHFFFAOYSA-M
  • Monoisotopic Mass: 260.016040317
  • Average Mass: 261.116
DBSALT000190
Categories
UNII19QM69HH21
CAS number155-97-5
WeightAverage: 181.2117
Monoisotopic: 181.09770267
Chemical FormulaC9H13N2O2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinium derivatives. These are compounds containing a pyridinium ring, which is the cationic form of pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinium derivatives
Direct ParentPyridinium derivatives
Alternative Parents
Substituents
  • Pyridinium
  • Heteroaromatic compound
  • Tertiary amine
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of myasthenia gravis.
PharmacodynamicsPyridostigmine 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 actionPyridostigmine 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.
Related Articles
AbsorptionPoorly absorbed from the GI tract with an oral bioavailability of 7.6 +/- 2.4%.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hydrolysis by cholinesterases and by liver.

Route of eliminationNot Available
Half life3 hours following oral administration.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Syruporal60 mg/5mL
Tabletoral60 mg
Tablet (extended-release)oral180 mg
Tabletoral60 mg/1
Tablet, extended releaseoral180 mg/1
Injection, solutionintravenous; parenteral5 mg/mL
Liquidintramuscular; intravenous5 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point153 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 ]
External Links
ATC CodesN07AA02
AHFS Codes
  • 12:04.00
PDB Entries
FDA labelDownload (120 KB)
MSDSDownload (74.6 KB)
Interactions
Drug Interactions
Drug
AcetylcholineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Acetylcholine.
Atracurium besylatePyridostigmine may decrease the neuromuscular blocking activities of Atracurium besylate.
CarbacholThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Carbachol.
DipyridamoleThe therapeutic efficacy of Pyridostigmine can be decreased when used in combination with Dipyridamole.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Pyridostigmine.
MethocarbamolThe therapeutic efficacy of Pyridostigmine can be decreased when used in combination with Methocarbamol.
NadololPyridostigmine may increase the bradycardic activities of Nadolol.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Pyridostigmine.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Pyridostigmine.
Food Interactions
  • Take with food to decrease adverse effects.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistinhibitor
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
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
Human
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
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23