Identification

Name
Neostigmine
Accession Number
DB01400
Type
Small Molecule
Groups
Approved, Vet Approved
Description

A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. [PubChem]

Structure
Thumb
Synonyms
  • (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate
  • 3-Trimethylammoniumphenyl N,N-dimethylcarbamate
  • Eustigmin
  • Eustigmine
  • m-Trimethylammoniumphenyldimethylcarbamate
Product Ingredients
IngredientUNIICASInChI Key
Neostigmine bromide005SYP50G5114-80-7LULNWZDBKTWDGK-UHFFFAOYSA-M
Neostigmine methylsulfate98IMH7M38651-60-5OSZNNLWOYWAHSS-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BloxiverzInjection.5 mg/mLIntravenousAvadel Legacy Pharmaceuticals, Llc2013-07-24Not applicableUs
BloxiverzInjection.5 mg/mLIntravenousAvadel Legacy Pharmaceuticals, Llc2013-07-24Not applicableUs
BloxiverzInjection1 mg/mLIntravenousAvadel Legacy Pharmaceuticals, Llc2013-07-24Not applicableUs
BloxiverzInjection1 mg/mLIntravenousAvadel Legacy Pharmaceuticals, Llc2013-07-24Not applicableUs
Neostigmine MethylsulfateInjection, solution.5 mg/mLIntravenousFresenius Kabi2015-01-08Not applicableUs
Neostigmine MethylsulfateInjection, solution1 mg/mLIntravenousRemedy Repack2015-10-19Not applicableUs
Neostigmine MethylsulfateInjection, solution1 mg/mLIntravenousGeneral Injectables & Vaccines2016-08-11Not applicableUs
Neostigmine MethylsulfateInjection, solution1 mg/mLIntravenousFresenius Kabi2015-01-08Not applicableUs
Neostigmine Methylsulfate Inj 0.5mg/ml USPLiquid.5 mgIntramuscular; Intravenous; SubcutaneousDavid Bull Laboratories (Pty) Ltd.1992-12-311996-09-10Canada
Neostigmine Methylsulfate Inj 1mg/ml USPLiquid1 mgIntramuscular; Intravenous; SubcutaneousDavid Bull Laboratories (Pty) Ltd.1991-12-311996-09-10Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Neostigmine MethylsulfateInjection.5 mg/mLIntravenousPar Pharmaceutical2017-04-26Not applicableUs
Neostigmine MethylsulfateInjection.5 mg/mLIntravenousWest Ward Pharmaceutical2015-12-28Not applicableUs
Neostigmine MethylsulfateInjection1 mg/mLIntravenousPar Pharmaceutical2017-04-26Not applicableUs
Neostigmine MethylsulfateInjection.5 mg/mLIntravenousAmphastar Pharmaceuticals, Inc.2017-09-25Not applicableUs
Neostigmine MethylsulfateInjection1 mg/mLIntravenousWest Ward Pharmaceutical2015-12-28Not applicableUs
Neostigmine MethylsulfateInjection1 mg/mLIntravenousAmphastar Pharmaceuticals, Inc.2017-09-25Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Neostigmine MethylsulfateInjection, solution1 mg/mLIntramuscular; Intravenous; SubcutaneousFresenius Kabi2000-09-012016-12-10Us
Neostigmine MethylsulfateInjection, solution1 mg/mLIntramuscular; Intravenous; SubcutaneousAmerican Regent2003-01-162016-10-19Us
Neostigmine MethylsulfateInjection1 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1973-01-012017-07-07Us
Neostigmine MethylsulfateInjection, solution1 mg/mLIntravenousCantrell Drug Company2015-02-03Not applicableUs
Neostigmine MethylsulfateInjection, solution.5 mg/mLIntramuscular; Intravenous; SubcutaneousAmerican Regent2003-01-172016-10-19Us
Neostigmine MethylsulfateInjection1 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1973-01-012017-07-07Us
Neostigmine MethylsulfateInjection, solution5 mg/mLIntramuscular; Intravenous; SubcutaneousFresenius Kabi2000-10-182016-12-10Us
Neostigmine MethylsulfateInjection.5 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1973-01-012017-07-07Us
Neostigmine MethylsulfateInjection.5 mg/mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1973-01-012017-07-07Us
International/Other Brands
Prostigmin / Vagostigmin
Categories
UNII
3982TWQ96G
CAS number
59-99-4
Weight
Average: 223.2915
Monoisotopic: 223.144652862
Chemical Formula
C12H19N2O2
InChI Key
ALWKGYPQUAPLQC-UHFFFAOYSA-N
InChI
InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium
SMILES
CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

Pharmacology

Indication

Neostigmine is used for the symptomatic treatment of myasthenia gravis by improving muscle tone.

Structured Indications
Pharmacodynamics

Neostigmine is a cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. By inhibiting acetylcholinesterase, more acetylcholine is available in the synapse, therefore, more of it can bind to the fewer receptors present in myasthenia gravis and can better trigger muscular contraction.

Mechanism of action

Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. The drug inhibits acetylcholinesterase which is responsible for the degredation of acetylcholine. So, with acetylcholinesterase inhibited, more acetylcholine is present By interfering with the breakdown of acetylcholine, neostigmine indirectly stimulates both nicotinic and muscarinic receptors which are involved in muscle contraction.. It does not cross the blood-brain barrier.

TargetActionsOrganism
AAcetylcholinesterase
inhibitor
Human
Absorption

Neostigmine bromide is poorly absorbed from the gastrointestinal tract following oral administration

Volume of distribution
Not Available
Protein binding

Protein binding to human serum albumin ranges from 15 to 25 percent.

Metabolism

Neostigmine undergoes hydrolysis by cholinesterase and is also metabolized by microsomal enzymes in the liver.

Route of elimination
Not Available
Half life

The half-life ranged from 42 to 60 minutes with a mean half-life of 52 minutes.

Clearance
Not Available
Toxicity

Overdosage of Neostigmine can cause cholinergic crisis, which is characterized by increasing muscle weakness, and through involvement of the muscles of respiration, may result in death. The LD 50 of neostigmine methylsulfate in mice is 0.3 ± 0.02 mg/kg intravenously, 0.54 ± 0.03 mg/kg subcutaneously, and 0.395 ± 0.025 mg/kg intramuscularly; in rats the LD 50 is 0.315 ± 0.019 mg/kg intravenously, 0.445 ± 0.032 mg/kg subcutaneously, and 0.423 ± 0.032 mg/kg intramuscularly.

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 Neostigmine.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Neostigmine.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Neostigmine.Experimental, Illicit
AcebutololNeostigmine may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Neostigmine.Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Neostigmine.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Neostigmine.Approved
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Neostigmine.Experimental
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Neostigmine.Experimental, Investigational
AlprenololNeostigmine may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Neostigmine.Approved
AndrostenedioneThe risk or severity of adverse effects can be increased when Androstenedione is combined with Neostigmine.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Neostigmine.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when anecortave acetate is combined with Neostigmine.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Neostigmine.Approved
ArecolineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Arecoline.Experimental
ArotinololNeostigmine may increase the bradycardic activities of Arotinolol.Approved, Investigational
AtamestaneThe risk or severity of adverse effects can be increased when Atamestane is combined with Neostigmine.Investigational
AtenololNeostigmine may increase the bradycardic activities of Atenolol.Approved
AtracuriumThe therapeutic efficacy of Atracurium can be decreased when used in combination with Neostigmine.Experimental, Investigational
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Neostigmine.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Neostigmine.Approved, Vet Approved
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Neostigmine.Approved, Investigational
BefunololNeostigmine may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Neostigmine.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Neostigmine.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Neostigmine.Approved, Vet Approved
BetaxololNeostigmine may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Neostigmine is combined with Bethanechol.Approved
BevantololNeostigmine may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Neostigmine.Approved, Investigational
BisoprololNeostigmine may increase the bradycardic activities of Bisoprolol.Approved
BopindololNeostigmine may increase the bradycardic activities of Bopindolol.Approved
BornaprineThe therapeutic efficacy of Bornaprine can be decreased when used in combination with Neostigmine.Experimental
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Neostigmine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Neostigmine.Approved
BucindololNeostigmine may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Neostigmine.Approved
BufuralolNeostigmine may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololNeostigmine may increase the bradycardic activities of Bupranolol.Approved
CarbacholThe risk or severity of adverse effects can be increased when Neostigmine is combined with Carbachol.Approved
CarteololNeostigmine may increase the bradycardic activities of Carteolol.Approved
CarvedilolNeostigmine may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololNeostigmine may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Neostigmine.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Neostigmine.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Neostigmine.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Neostigmine.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Clobetasone is combined with Neostigmine.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Neostigmine.Approved
CloranololNeostigmine may increase the bradycardic activities of Cloranolol.Experimental
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Neostigmine.Approved
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Cortexolone 17α-propionate is combined with Neostigmine.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Corticosterone is combined with Neostigmine.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Neostigmine.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Neostigmine.Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Neostigmine.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Neostigmine.Approved, Investigational
DeflazacortThe risk or severity of adverse effects can be increased when Deflazacort is combined with Neostigmine.Approved
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Neostigmine.Approved, Investigational
DesonideThe risk or severity of adverse effects can be increased when Desonide is combined with Neostigmine.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Neostigmine.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Neostigmine.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Neostigmine.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Neostigmine.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Neostigmine.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Neostigmine.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Neostigmine.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Neostigmine.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Neostigmine.Approved, Investigational
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Neostigmine.Approved
DipyridamoleThe therapeutic efficacy of Neostigmine can be decreased when used in combination with Dipyridamole.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Neostigmine.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Neostigmine.Approved
EmeproniumThe therapeutic efficacy of Emepronium can be decreased when used in combination with Neostigmine.Experimental
EpanololNeostigmine may increase the bradycardic activities of Epanolol.Experimental
EpibatidineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Epibatidine.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Neostigmine.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Neostigmine.Approved
EsmololNeostigmine may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Neostigmine.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Neostigmine.Approved
EtanautineThe therapeutic efficacy of Etanautine can be decreased when used in combination with Neostigmine.Experimental
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Neostigmine.Approved
EtybenzatropineThe therapeutic efficacy of Etybenzatropine can be decreased when used in combination with Neostigmine.Experimental
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Neostigmine.Approved
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Neostigmine.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Neostigmine.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Neostigmine.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Neostigmine.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Neostigmine.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Neostigmine.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Neostigmine.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Neostigmine.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Neostigmine.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Neostigmine.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Neostigmine.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Neostigmine.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Neostigmine.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Neostigmine.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Neostigmine.Approved, Investigational, Withdrawn
GallamineThe therapeutic efficacy of Gallamine can be decreased when used in combination with Neostigmine.Experimental
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Neostigmine.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Neostigmine.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Neostigmine is combined with GTS-21.Investigational
HalcinonideThe risk or severity of adverse effects can be increased when Halcinonide is combined with Neostigmine.Approved, Investigational, Withdrawn
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Neostigmine.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Neostigmine.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Neostigmine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Neostigmine.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Neostigmine.Approved
IndenololNeostigmine may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Neostigmine.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Neostigmine.Investigational
LabetalolNeostigmine may increase the bradycardic activities of Labetalol.Approved
LandiololNeostigmine may increase the bradycardic activities of Landiolol.Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Neostigmine.Approved
LevobunololNeostigmine may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Lobeline.Investigational
LoteprednolThe risk or severity of adverse effects can be increased when Loteprednol is combined with Neostigmine.Approved
MazaticolThe therapeutic efficacy of Mazaticol can be decreased when used in combination with Neostigmine.Experimental
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Neostigmine.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Neostigmine.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Neostigmine.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Neostigmine.Vet Approved
MepindololNeostigmine may increase the bradycardic activities of Mepindolol.Experimental
MethacholineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Neostigmine.Approved, Investigational
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Neostigmine.Approved, Vet Approved
Methylscopolamine bromideThe therapeutic efficacy of Methylscopolamine bromide can be decreased when used in combination with Neostigmine.Approved
MetipranololNeostigmine may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Neostigmine.Approved
MetoprololNeostigmine may increase the bradycardic activities of Metoprolol.Approved, Investigational
MivacuriumNeostigmine may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Neostigmine.Approved, Vet Approved
NadololNeostigmine may increase the bradycardic activities of Nadolol.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Neostigmine.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Neostigmine.Investigational
NebivololNeostigmine may increase the bradycardic activities of Nebivolol.Approved, Investigational
NicotineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Nicotine.Approved
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl-estrone is combined with Neostigmine.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Neostigmine.Approved
OtiloniumThe therapeutic efficacy of Otilonium can be decreased when used in combination with Neostigmine.Experimental, Investigational
OxitropiumThe therapeutic efficacy of Oxitropium can be decreased when used in combination with Neostigmine.Investigational
OxprenololNeostigmine may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Neostigmine.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Neostigmine.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Neostigmine.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Neostigmine.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Neostigmine.Approved
PenbutololNeostigmine may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Neostigmine.Approved
PhenglutarimideThe therapeutic efficacy of Phenglutarimide can be decreased when used in combination with Neostigmine.Experimental
PilocarpineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Pilocarpine.Approved
PindololNeostigmine may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Neostigmine.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Neostigmine.Approved
Platelet Activating FactorNeostigmine may increase the bradycardic activities of Platelet Activating Factor.Experimental
PractololNeostigmine may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Neostigmine.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with Neostigmine.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Neostigmine.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Neostigmine.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Neostigmine.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Neostigmine.Experimental, Investigational
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Neostigmine.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Neostigmine.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Neostigmine.Approved, Investigational
PropranololNeostigmine may increase the bradycardic activities of Propranolol.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Neostigmine.Approved
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Neostigmine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Neostigmine.Approved, Investigational
RapacuroniumNeostigmine may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Neostigmine.Approved, Investigational
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Neostigmine.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Neostigmine.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Neostigmine.Approved, Vet Approved
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Neostigmine.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Neostigmine.Approved
SotalolNeostigmine may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Neostigmine.Approved
TalinololNeostigmine may increase the bradycardic activities of Talinolol.Investigational
TertatololNeostigmine may increase the bradycardic activities of Tertatolol.Experimental
TimololNeostigmine may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Neostigmine.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Neostigmine.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Neostigmine.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Neostigmine.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Neostigmine.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Neostigmine.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Neostigmine.Approved, Investigational
TropatepineThe therapeutic efficacy of Tropatepine can be decreased when used in combination with Neostigmine.Experimental
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Neostigmine.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Neostigmine.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Neostigmine.Approved
UlobetasolThe risk or severity of adverse effects can be increased when Ulobetasol is combined with Neostigmine.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Neostigmine.Approved
VareniclineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Neostigmine.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Neostigmine.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15472
KEGG Compound
C07258
PubChem Compound
4456
PubChem Substance
46509161
ChemSpider
4301
BindingDB
50022775
ChEBI
7514
ChEMBL
CHEMBL278020
Therapeutic Targets Database
DAP000563
PharmGKB
PA450611
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Neostigmine
ATC Codes
N07AA51 — Neostigmine, combinationsS01EB06 — NeostigmineN07AA01 — Neostigmine
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentNeurogenic Bowel Dysfunction / Spinal Cord Injuries (SCI)1
0Not Yet RecruitingPreventionIncidence of Postoperative Residual Curarization1
0RecruitingTreatmentSnoring1
1Not Yet RecruitingTreatmentAcute Pancreatitis (AP) / Intra-Abdominal Hypertension1
1RecruitingNot AvailableGastrointestinal Dysfunction1
1, 2CompletedSupportive CareAdjunct to general anesthesia therapy / Smooth muscle relaxation prior to radiological procedures1
2RecruitingSupportive CareCancer, Breast1
2, 3Active Not RecruitingPreventionAdjuvants, Anesthesia1
2, 3CompletedPreventionHypospadias1
2, 3RecruitingTreatmentKnee Injuries1
2, 3RecruitingTreatmentPostoperative pain1
2, 3Unknown StatusTreatmentNeuromuscular Blockade / Obesity, Morbid1
3CompletedTreatmentAnaesthesia therapy2
3CompletedTreatmentAntithrombotic Agents / Arthroplasty, Replacement, Hip / Arthroplasty, Replacement, Knee / Coagulation, Blood / Neuromuscular Blockade1
3CompletedTreatmentDiaphragmatic Dysfunction / Muscle Fatigue / Muscle Weakness1
3CompletedTreatmentNeuromuscular Blockade2
3CompletedTreatmentAdjunct to general anesthesia therapy / Neuromuscular Blockade1
3CompletedTreatmentSurgical Procedures, Elective1
3CompletedTreatmentAdjunct to general anesthesia therapy4
3RecruitingTreatmentGeneral Surgery1
4Active Not RecruitingSupportive CareMuscle Relaxation1
4CompletedBasic ScienceElectromyography / Respiratory Muscles1
4CompletedDiagnosticIntraocular Pressure Changes During Tracheal Extubation1
4CompletedDiagnosticSphincter of Oddi Dysfunction1
4CompletedDiagnosticSpinal Cord Injuries (SCI)1
4CompletedPreventionIncidence of Postoperative Nausea and Vomiting1
4CompletedScreeningSpinal Curvatures1
4CompletedSupportive CareBMI >30 kg/m2 / Cerebral Tissue Oxygenation / Laparoscopic Gastric Bypass Surgery / Respiratory Function / Surgical Conditions1
4CompletedSupportive CareIleus1
4CompletedTreatmentAirway Reflexes, Protective / Anesthetic Recovery / Recovery After Neuromuscular Block1
4CompletedTreatmentAnaesthesia1
4CompletedTreatmentCaesarean Sections / Pregnancy1
4CompletedTreatmentCirrhosis and Chronic Liver Disease1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentMajor Abdominal Surgery1
4CompletedTreatmentNeuromuscular Block1
4CompletedTreatmentObstructive Sleep Apnea (OSA)1
4CompletedTreatmentParalysis1
4CompletedTreatmentPostoperative Respiratory Condition1
4CompletedTreatmentRespiratory-Gated Imaging Techniques1
4CompletedTreatmentReversal of Skeletal Muscle Relaxant / Underdosing of Skeletal Muscle Relaxants for Laparotomy1
4Enrolling by InvitationPreventionNeuromuscular Blockade / Postoperative Complications1
4Enrolling by InvitationTreatmentNeuromuscular Blockade1
4Not Yet RecruitingPreventionEmergence Delirium1
4Not Yet RecruitingPreventionPulmonary Complications1
4Not Yet RecruitingTreatmentAnaesthesia therapy / Neuromuscular Blockade1
4Not Yet RecruitingTreatmentMalignant Neoplasms of Digestive Organs / Malignant Neoplasms of Female Genital Organs / Malignant Neoplasms of Male Genital Organs / Malignant Neoplasms of Urinary Tract1
4Not Yet RecruitingTreatmentRespiratory Insufficiency1
4RecruitingOtherNeuromuscular Blockade1
4RecruitingSupportive CareBladder Cancers / Malignant Neoplasms of Urinary Tract1
4RecruitingTreatmentAnesthesia Recovery Period / Laparoscopy1
4RecruitingTreatmentIncomplete Reversal of Neuromuscular Block1
4RecruitingTreatmentMicrolaryngoscopy / Rigid Bronchoscopy1
4RecruitingTreatmentNeuromuscular Blockade2
4RecruitingTreatmentPost-operative Residual Curarization1
4RecruitingTreatmentSpine Surgery1
4Unknown StatusSupportive CareAnesthesia Recovery Period1
4Unknown StatusTreatmentAnesthesia Recovery1
4Unknown StatusTreatmentNeuromuscular Blockade1
4WithdrawnNot AvailableNeuromuscular Blockade1
Not AvailableCompletedNot AvailableNeuromuscular Blockade1
Not AvailableCompletedNot AvailableResidual Neuromuscular Block (TOF-ratio of 0.2)1
Not AvailableCompletedOtherAnesthesiology Management1
Not AvailableCompletedScreeningPost Operative Cognitive Dysfunction1
Not AvailableCompletedSupportive CareRobot-Assisted Laparoscopic Radical Prostatectomy1
Not AvailableCompletedTreatmentLabour Pain1
Not AvailableCompletedTreatmentNeuromuscular Blockade1
Not AvailableCompletedTreatmentObesity, Morbid / Respiratory Complications1
Not AvailableCompletedTreatmentObservation of Neuromuscular Block1
Not AvailableCompletedTreatmentAdjunct to general anesthesia therapy1
Not AvailableEnrolling by InvitationSupportive CareSupratentorial Brain Tumor Surgery1
Not AvailableNot Yet RecruitingNot AvailableProphylaxis against postoperative nausea and vomiting / Respiratory Conditions Due to Other External Agents1
Not AvailableRecruitingNot AvailableResidual Neuromuscular Blockade1
Not AvailableRecruitingDiagnosticBlood Coagulation Tests ( INR, APTT)1
Not AvailableRecruitingOtherPostoperative Residual Curarization / Transplantation, Liver1
Not AvailableRecruitingSupportive CareNeuromuscular Block, Residual1
Not AvailableUnknown StatusTreatmentPregnancy / Vaginal Delivery1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
InjectionIntramuscular; Intravenous; Subcutaneous.5 mg/mL
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/mL
InjectionIntravenous.5 mg/mL
InjectionIntravenous1 mg/mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous.5 mg/mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous1 mg/mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous5 mg/mL
Injection, solutionIntravenous.5 mg/mL
Injection, solutionIntravenous1 mg/mL
SolutionIntramuscular; Intravenous; Subcutaneous0.5 mg
SolutionIntramuscular; Intravenous; Subcutaneous2.5 mg
LiquidIntramuscular; Intravenous; Subcutaneous0.5 mg
LiquidIntramuscular; Intravenous; Subcutaneous1 mg
LiquidIntramuscular; Intravenous; Subcutaneous.5 mg
TabletOral15 mg
Prices
Unit descriptionCostUnit
Neostigmine bromide powder96.57USD g
Neostigmine ms 5 mg/5 ml syr1.99USD ml
Prostigmin 1:4000 ampul1.42USD ml
Prostigmin 15 mg tablet1.04USD tablet
Neostigmine 1:1000 vial0.48USD ml
Neostigmine 1:2000 vial0.48USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0677 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.2ChemAxon
logS-3.6ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.28 m3·mol-1ChemAxon
Polarizability25.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8576
Blood Brain Barrier+0.9583
Caco-2 permeable+0.608
P-glycoprotein substrateNon-substrate0.8263
P-glycoprotein inhibitor INon-inhibitor0.9598
P-glycoprotein inhibitor IINon-inhibitor0.9279
Renal organic cation transporterNon-inhibitor0.9181
CYP450 2C9 substrateNon-substrate0.7197
CYP450 2D6 substrateNon-substrate0.6869
CYP450 3A4 substrateSubstrate0.622
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9367
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9424
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8362
Ames testAMES toxic0.5146
CarcinogenicityNon-carcinogens0.5931
BiodegradationNot ready biodegradable0.7893
Rat acute toxicity2.9481 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.952
hERG inhibition (predictor II)Non-inhibitor0.8738
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
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0090000000-7feec7180feed2165741
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0090000000-33ad4a0e0807f82bab39
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-2090000000-285ee2bce4f4c2097510
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9110000000-a2386202e9dc8c7c753f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-b80120a3f55bb762fe51
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0a4i-0090000000-675c3ee4663579ce2125

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenoxy compounds
Direct Parent
Phenoxy compounds
Alternative Parents
Aniline and substituted anilines / Quaternary ammonium salts / Carbamate esters / Organic carbonic acids and derivatives / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Amines
show 1 more
Substituents
Phenoxy compound / Aniline or substituted anilines / Quaternary ammonium salt / Carbamic acid ester / Carbonic acid derivative / Amine / Carbonyl group / Hydrocarbon derivative / Organic oxide / Organic salt
show 7 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
quaternary ammonium ion (CHEBI:7514)

Targets

Details
1. Acetylcholinesterase
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
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. Trevisani GT, Hyman NH, Church JM: Neostigmine: safe and effective treatment for acute colonic pseudo-obstruction. Dis Colon Rectum. 2000 May;43(5):599-603. [PubMed:10826417]
  2. Naves LA, Van der Kloot W: Repetitive nerve stimulation decreases the acetylcholine content of quanta at the frog neuromuscular junction. J Physiol. 2001 May 1;532(Pt 3):637-47. [PubMed:11313435]
  3. Takeuchi K, Kawauchi S, Araki H, Ueki S, Furukawa O: Stimulation by nizatidine, a histamine H(2)-receptor antagonist, of duodenal HCO(3)(-)secretion in rats:relation to anti-cholinesterase activity. World J Gastroenterol. 2000 Oct;6(5):651-658. [PubMed:11819669]
  4. Minic J, Chatonnet A, Krejci E, Molgo J: Butyrylcholinesterase and acetylcholinesterase activity and quantal transmitter release at normal and acetylcholinesterase knockout mouse neuromuscular junctions. Br J Pharmacol. 2003 Jan;138(1):177-87. [PubMed:12522088]
  5. Beck KD, Brennan FX, Moldow RL, Ottenweller JE, Zhu G, Servatius RJ: Stress interacts with peripheral cholinesterase inhibitors to cause central nervous system effects. Life Sci. 2003 May 23;73(1):41-51. [PubMed:12726885]
  6. Zhang B, Hepner DL, Tran MH, Friedman M, Korn JR, Menzin J: Neuromuscular blockade, reversal agent use, and operating room time: retrospective analysis of US inpatient surgeries. Curr Med Res Opin. 2009 Apr;25(4):943-50. doi: 10.1185/03007990902769054 . [PubMed:19257799]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Saito S: Cholinesterase inhibitors induce growth cone collapse and inhibit neurite extension in primary cultured chick neurons. Neurotoxicol Teratol. 1998 Jul-Aug;20(4):411-9. [PubMed:9697967]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674]

Drug created on July 08, 2007 11:06 / Updated on November 19, 2017 20:33