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Identification
NamePyridostigmine
Accession NumberDB00545  (APRD00380)
TypeSmall Molecule
GroupsApproved
DescriptionA 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
MestinonSyrup60 mg/5mLOralValeant Pharmaceuticals North America LLC1965-01-25Not applicableUs
MestinonTablet, extended release180 mg/1OralValeant Pharmaceuticals North America LLC1959-01-12Not 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 BromideTablet, extended release180 mg/1OralOceanside Pharmaceuticals1959-01-12Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralOceanside Pharmaceuticals2007-10-30Not 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 BromideTablet60 mg/1OralImpax Generics2003-04-24Not applicableUs
Pyridostigmine BromideTablet, extended release180 mg/1OralImpax Generics2015-09-18Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralCadila Healthcare Limited2015-08-07Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralKAISER FOUNDATION HOSPITALS2010-08-02Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralAmerican Health Packaging2011-09-30Not applicableUs
Pyridostigmine BromideTablet, extended release180 mg/1OralAlvogen Inc.2015-06-29Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralZydus Pharmaceuticals (USA) Inc.2015-08-07Not applicableUs
Pyridostigmine BromideTablet60 mg/1OralREMEDYREPACK INC.2011-10-042016-11-29Us
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 KeyRVOLLAQWKVFTGE-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
IndicationFor the treatment of myasthenia gravis.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
AcetylcholinesteraseProteinyes
antagonist
inhibitor
HumanP22303 details
CholinesteraseProteinyes
antagonist
HumanP06276 details
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
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
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione 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
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Pyridostigmine.Experimental
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
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Pyridostigmine.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Pyridostigmine.Approved
Aop200704Pyridostigmine may increase the bradycardic activities of Aop200704.Investigational
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.Approved
AtenololPyridostigmine may increase the bradycardic activities of Atenolol.Approved
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
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Pyridostigmine.Investigational
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
BisoprololPyridostigmine may increase the bradycardic activities of Bisoprolol.Approved
BopindololPyridostigmine may increase the bradycardic activities of Bopindolol.Approved
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
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
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Pyridostigmine.Approved
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
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Pyridostigmine.Investigational
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination 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
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
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
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Pyridostigmine.Approved
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
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
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
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
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
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
MethocarbamolThe therapeutic efficacy of Pyridostigmine can be decreased when used in combination with Methocarbamol.Approved, Vet Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Pyridostigmine.Approved, Vet 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
MivacuriumPyridostigmine may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Pyridostigmine.Approved, Vet Approved
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Pyridostigmine.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
NicotineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Nicotine.Approved
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Nicotine bitartrate.Approved
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Pyridostigmine.Investigational
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
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
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
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
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
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.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
RapacuroniumPyridostigmine may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
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
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide 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
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
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
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
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
ATC CodesN07AA02
AHFS Codes
  • 12:04.00
PDB Entries
FDA labelDownload (120 KB)
MSDSDownload (74.6 KB)
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 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.
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
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

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