Identification

Name
Pyridostigmine
Accession Number
DB00545  (APRD00380)
Type
Small Molecule
Groups
Approved
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
  • Pyridostigmin bromid
  • Pyridostigmine
  • Pyridostigmini Bromidum
Product Ingredients
IngredientUNIICASInChI Key
Pyridostigmine BromideKVI301NA53101-26-8VNYBTNPBYXSMOO-UHFFFAOYSA-M
Pyridostigmine chloride45X1P9AO697681-22-3TYXYRYORUZYJDX-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MestinonTablet60 mg/1OralValeant Pharmaceuticals North America1955-04-06Not applicableUs
MestinonTablet, extended release180 mg/1OralValeant Pharmaceuticals North America1959-01-12Not applicableUs
MestinonSyrup60 mg/5mLOralValeant Pharmaceuticals North America1965-01-25Not applicableUs
Mestinon Tab 60mg USPTablet60 mgOralValeant Canada Lp Valeant Canada S.E.C.1990-12-31Not applicableCanada
Mestinon-SRTablet, extended release180 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; ParenteralSandoz2005-05-10Not applicableUs
Regonol Inj 5mg/mlLiquid5 mgIntramuscular; IntravenousOrganon Canada Ltd Ltee1977-12-311999-08-11Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pyridostigmine BromideTablet60 mg/1OralRemedy Repack2011-10-042016-11-29Us00115 3511 01 nlmimage10 c60e6313
Pyridostigmine BromideTablet60 mg/1OralMajor2015-08-07Not applicableUs
Pyridostigmine BromideTablet, extended release180 mg/1OralImpax Generics2015-09-18Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralZydus Pharmaceuticals Usa, Inc.2015-08-07Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralKaiser Foundations Hospitals2010-08-022017-12-22Us
Pyridostigmine BromideTablet60 mg/1Oralbryant ranch prepack2015-08-07Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralCadila Pharnmaceuticals2015-08-07Not applicableUs
Pyridostigmine BromideTablet, extended release180 mg/1OralAlvogen, Inc.2015-06-29Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralImpax Generics2003-04-24Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralAmerincan Health Packaging2011-09-30Not applicableUs
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 / Mestinon retard (Meda) / Myestin (VHB) / Pyrimine (Sriprasit Dispensary) / Regonol
Categories
UNII
19QM69HH21
CAS number
155-97-5
Weight
Average: 181.2117
Monoisotopic: 181.09770267
Chemical Formula
C9H13N2O2
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

Pharmacology

Indication

For the treatment of myasthenia gravis.

Structured Indications
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
Human
ACholinesterase
antagonist
Human
USerum albuminNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Pyridostigmine.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Pyridostigmine.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Pyridostigmine.Experimental, Illicit
AcebutololPyridostigmine may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Pyridostigmine.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Pyridostigmine.Approved
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Pyridostigmine.Experimental
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Pyridostigmine.Experimental, Investigational
AlprenololPyridostigmine may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Pyridostigmine.Approved
AndrostenedioneThe risk or severity of adverse effects can be increased when Androstenedione is combined with Pyridostigmine.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Pyridostigmine.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when anecortave acetate is combined with Pyridostigmine.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Pyridostigmine.Approved
ArecolineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Arecoline.Experimental
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Pyridostigmine.Approved, Investigational
ArotinololPyridostigmine may increase the bradycardic activities of Arotinolol.Investigational
AtamestaneThe risk or severity of adverse effects can be increased when Atamestane is combined with Pyridostigmine.Investigational
AtenololPyridostigmine may increase the bradycardic activities of Atenolol.Approved
AtracuriumThe therapeutic efficacy of Atracurium can be decreased when used in combination with Pyridostigmine.Experimental, Investigational
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Pyridostigmine.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Pyridostigmine.Approved, Vet Approved
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Pyridostigmine.Approved, Investigational
BefunololPyridostigmine may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Pyridostigmine.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Pyridostigmine.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Pyridostigmine.Approved, Vet Approved
BetaxololPyridostigmine may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Bethanechol.Approved
BevantololPyridostigmine may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Pyridostigmine.Approved, Investigational
BisoprololPyridostigmine may increase the bradycardic activities of Bisoprolol.Approved
BopindololPyridostigmine may increase the bradycardic activities of Bopindolol.Approved
BornaprineThe therapeutic efficacy of Bornaprine can be decreased when used in combination with Pyridostigmine.Experimental
BucindololPyridostigmine may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Pyridostigmine.Approved
BufuralolPyridostigmine may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololPyridostigmine may increase the bradycardic activities of Bupranolol.Approved
ButylscopolamineThe therapeutic efficacy of Butylscopolamine can be decreased when used in combination with Pyridostigmine.Approved, Vet Approved
CarbacholThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Carbachol.Approved
CarteololPyridostigmine may increase the bradycardic activities of Carteolol.Approved
CarvedilolPyridostigmine may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololPyridostigmine may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Pyridostigmine.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Pyridostigmine.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Pyridostigmine.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Pyridostigmine.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Clobetasone is combined with Pyridostigmine.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Pyridostigmine.Approved
CloranololPyridostigmine may increase the bradycardic activities of Cloranolol.Experimental
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Cortexolone 17α-propionate is combined with Pyridostigmine.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Corticosterone is combined with Pyridostigmine.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Pyridostigmine.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Pyridostigmine.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Pyridostigmine.Approved, Investigational
DeflazacortThe risk or severity of adverse effects can be increased when Deflazacort is combined with Pyridostigmine.Approved, Investigational
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Pyridostigmine.Approved, Investigational
DesonideThe risk or severity of adverse effects can be increased when Desonide is combined with Pyridostigmine.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Pyridostigmine.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Pyridostigmine.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Pyridostigmine.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Pyridostigmine.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Pyridostigmine.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Pyridostigmine.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Pyridostigmine.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Pyridostigmine.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Pyridostigmine.Approved, Investigational, Withdrawn
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Pyridostigmine.Approved
DipyridamoleThe therapeutic efficacy of Pyridostigmine can be decreased when used in combination with Dipyridamole.Approved
EmeproniumThe therapeutic efficacy of Emepronium can be decreased when used in combination with Pyridostigmine.Experimental
EpanololPyridostigmine may increase the bradycardic activities of Epanolol.Experimental
EpibatidineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Epibatidine.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Pyridostigmine.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Pyridostigmine.Approved
EsmololPyridostigmine may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Pyridostigmine.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Pyridostigmine.Approved
EtanautineThe therapeutic efficacy of Etanautine can be decreased when used in combination with Pyridostigmine.Experimental
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Pyridostigmine.Approved
EtybenzatropineThe therapeutic efficacy of Etybenzatropine can be decreased when used in combination with Pyridostigmine.Experimental
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Pyridostigmine.Approved
FluasteroneThe risk or severity of adverse effects can be increased when Fluasterone is combined with Pyridostigmine.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Pyridostigmine.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Pyridostigmine.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Pyridostigmine.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Pyridostigmine.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Pyridostigmine.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Pyridostigmine.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Pyridostigmine.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Pyridostigmine.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Pyridostigmine.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Pyridostigmine.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Pyridostigmine.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Pyridostigmine.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Pyridostigmine.Approved, Investigational, Withdrawn
GallamineThe therapeutic efficacy of Gallamine can be decreased when used in combination with Pyridostigmine.Experimental
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Pyridostigmine.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Pyridostigmine.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Pyridostigmine is combined with GTS-21.Investigational
HalcinonideThe risk or severity of adverse effects can be increased when Halcinonide is combined with Pyridostigmine.Approved, Investigational, Withdrawn
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Pyridostigmine.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Pyridostigmine.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Pyridostigmine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Pyridostigmine.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Pyridostigmine.Approved
IndenololPyridostigmine may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Pyridostigmine.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Pyridostigmine.Investigational
LabetalolPyridostigmine may increase the bradycardic activities of Labetalol.Approved
LandiololPyridostigmine may increase the bradycardic activities of Landiolol.Investigational
LevobunololPyridostigmine may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Lobeline.Investigational
LoteprednolThe risk or severity of adverse effects can be increased when Loteprednol is combined with Pyridostigmine.Approved
MazaticolThe therapeutic efficacy of Mazaticol can be decreased when used in combination with Pyridostigmine.Experimental
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Pyridostigmine.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Pyridostigmine.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Pyridostigmine.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Pyridostigmine.Vet Approved
MepindololPyridostigmine may increase the bradycardic activities of Mepindolol.Experimental
MethacholineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Pyridostigmine.Approved, Investigational
MethocarbamolThe therapeutic efficacy of Pyridostigmine can be decreased when used in combination with Methocarbamol.Approved, Vet Approved
MethscopolamineThe therapeutic efficacy of Methscopolamine can be decreased when used in combination with Pyridostigmine.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Pyridostigmine.Approved, Vet Approved
Methylscopolamine bromideThe therapeutic efficacy of Methylscopolamine bromide can be decreased when used in combination with Pyridostigmine.Approved
MetipranololPyridostigmine may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Pyridostigmine.Approved
MetoprololPyridostigmine may increase the bradycardic activities of Metoprolol.Approved, Investigational
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Pyridostigmine.Approved, Vet Approved
NadololPyridostigmine may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Pyridostigmine.Investigational
NebivololPyridostigmine may increase the bradycardic activities of Nebivolol.Approved, Investigational
NicotineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Nicotine.Approved
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl-estrone is combined with Pyridostigmine.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Pyridostigmine.Approved
OtiloniumThe therapeutic efficacy of Otilonium can be decreased when used in combination with Pyridostigmine.Experimental, Investigational
OxitropiumThe therapeutic efficacy of Oxitropium can be decreased when used in combination with Pyridostigmine.Investigational
OxprenololPyridostigmine may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Pyridostigmine.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Pyridostigmine.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Pyridostigmine.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Pyridostigmine.Approved
PenbutololPyridostigmine may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Pyridostigmine.Approved
PhenglutarimideThe therapeutic efficacy of Phenglutarimide can be decreased when used in combination with Pyridostigmine.Experimental
PilocarpineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Pilocarpine.Approved
PindololPyridostigmine may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Pyridostigmine.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Pyridostigmine.Approved
Platelet Activating FactorPyridostigmine may increase the bradycardic activities of Platelet Activating Factor.Experimental
PractololPyridostigmine may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Pyridostigmine.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with Pyridostigmine.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Pyridostigmine.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Pyridostigmine.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Pyridostigmine.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Pyridostigmine.Experimental, Investigational
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Pyridostigmine.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Pyridostigmine.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Pyridostigmine.Approved, Investigational
PropranololPyridostigmine may increase the bradycardic activities of Propranolol.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Pyridostigmine.Approved
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Pyridostigmine.Approved
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Pyridostigmine.Approved
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Pyridostigmine.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Pyridostigmine.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Pyridostigmine.Approved
SotalolPyridostigmine may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Pyridostigmine.Approved
TalinololPyridostigmine may increase the bradycardic activities of Talinolol.Investigational
TertatololPyridostigmine may increase the bradycardic activities of Tertatolol.Experimental
TimololPyridostigmine may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Pyridostigmine.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Pyridostigmine.Approved, Withdrawn
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Pyridostigmine.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Pyridostigmine.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Pyridostigmine.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Pyridostigmine.Approved, Investigational
TropatepineThe therapeutic efficacy of Tropatepine can be decreased when used in combination with Pyridostigmine.Experimental
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Pyridostigmine.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Pyridostigmine.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Pyridostigmine.Approved
UlobetasolThe risk or severity of adverse effects can be increased when Ulobetasol is combined with Pyridostigmine.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Pyridostigmine.Approved
VareniclineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Pyridostigmine.Approved
Food Interactions
  • Take with food to decrease adverse effects.

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
Human Metabolome Database
HMDB0014685
KEGG Drug
D00487
KEGG Compound
C07410
PubChem Compound
4991
PubChem Substance
46506129
ChemSpider
4817
BindingDB
50313079
ChEBI
8665
ChEMBL
CHEMBL1115
Therapeutic Targets Database
DNC001171
PharmGKB
PA451185
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pyridostigmine
ATC Codes
N07AA02 — Pyridostigmine
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
FDA label
Download (120 KB)
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingDiagnosticOrthostatic Intolerance / Postural Orthostatic Tachycardia Syndrome (POTS) / POTS1
0RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
0TerminatedTreatmentPompe's Disease1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1RecruitingBasic ScienceDiabetes Mellitus (DM)1
1RecruitingBasic SciencePostural Tachycardia Syndrome1
1, 2CompletedTreatmentColonic Transit / Diabetes Mellitus (DM) / Gastric Emptying / Occasional Constipation1
2Active Not RecruitingTreatmentAutonomic Disturbances in Parkinson's Disease1
2Active Not RecruitingTreatmentCD4+ T Lymphocytopenia / HIV-1-infection / Immune Deficiencies / Immuno-senescence1
2Active Not RecruitingTreatmentKugelberg-Welander Disease / SMA / Spinal Muscular Atrophy (SMA)1
2CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentFibromyalgia1
2CompletedTreatmentHeart Failure, Unspecified1
2CompletedTreatmentIdiopathic orthostatic hypotension1
2RecruitingTreatmentAutonomic Dysreflexia / Autonomic Integrity / Baroreceptor Integrity / Blood Pressures / Cerebral Blood Flow / Cognitive Function / Hypotensive / Spinal Cord Injuries (SCI) / Sympathetic Integrity / Vagal Integrity1
2RecruitingTreatmentSpinal Muscular Atrophy Type 31
2RecruitingTreatmentIdiopathic orthostatic hypotension1
3CompletedTreatmentLeukemias1
3TerminatedTreatmentOcular Myasthenia Gravis1
4Active Not RecruitingSupportive CareMuscle Relaxation1
4Active Not RecruitingTreatmentPostural Orthostatic Tachycardia Syndrome (POTS)1
4RecruitingTreatmentOrthostatic; Hypotension, Neurogenic1
Not AvailableCompletedTreatmentDiabetes Complications1
Not AvailableRecruitingTreatmentPostural Tachycardia Syndrome1

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 releaseOral180 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.
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

Taxonomy

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
N-methylpyridinium / Pyridinium / Carbamic acid ester / Heteroaromatic compound / Carbonic acid derivative / Azacycle / Organic oxide / Organopnictogen compound / Organic oxygen compound / Organooxygen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:8665)

Targets

Kind
Protein
Organism
Human
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
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
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
Human
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]

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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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]

Drug created on June 13, 2005 07:24 / Updated on January 22, 2018 10:45