Drug Details

General Information of the Drug (ID: DR0176)
Name
Neostigmine
Synonyms
NEOSTIGMINE; Eustigmin; Eustigmine; Prostigmine; Vagostigmine; Prostigmin; 59-99-4; Juvastigmin; m-Trimethylammoniumphenyldimethylcarbamate; Neostigmine [BAN]; 3-Trimethylammoniumphenyl N,N-dimethylcarbamate; 3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium; Vagostigmin; Neostigmine (BAN); UNII-3982TWQ96G; (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate; Prostigmin (TN); Neostigmin; CHEBI:7514; CHEMBL278020; Intrastigmina; Neostigminum; Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-; 3982TWQ96G; [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium bromide; 3-{[(dimethylamino)carbonyl]oxy}-N,N,N-trimethylanilinium; Benzenaminium, 3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-; 3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium; [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; sulfonatooxymethane; CCRIS 3079; HSDB 3921; NCGC00163240-01; CAS-114-80-7; BRN 3615946; (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate (ester); Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester); [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium; Spectrum_001061; Prestwick0_000468; Prestwick1_000468; Prestwick2_000468; Prestwick3_000468; Spectrum2_001278; Spectrum4_000072; Spectrum5_001234; Lopac-N-2001; bmse000762; Lopac0_000816; SCHEMBL34419; BSPBio_000576; KBioGR_000623; KBioSS_001541; [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; DivK1c_000165; DivK1c_000198; SPBio_001276; SPBio_002515; BPBio1_000634; GTPL8993; ZINC1792; DTXSID1023360; ALWKGYPQUAPLQC-UHFFFAOYSA-; KBio1_000165; KBio1_000198; KBio2_001541; KBio2_004109; KBio2_006677; NINDS_000165; NINDS_000198; HMS2089A22; BDBM50022775; STL058953; AKOS005711366; CCG-204900; DB01400; MCULE-3501840981; IDI1_000165; IDI1_000198; MLS-0002855; NCGC00015730-01; NCGC00015730-02; NCGC00015730-03; NCGC00015730-04; NCGC00015730-05; NCGC00015730-06; NCGC00015730-07; NCGC00015730-08; NCGC00015730-09; NCGC00015730-24; NCGC00021658-03; SBI-0050793.P004; AB00053807; C07258; D08261; AB00053807-25; AB00053807-26; AB00053807_27; AB00053807_28; AB00053807_29; Q410546; BRD-K18922609-004-04-1; BRD-K18922609-004-14-0; Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl- (9CI)
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Molecular Type
Small molecule
Disease Myasthenia gravis [ICD-11: 8C6Y] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 9.2 mL/min/kg
Elimination
67% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 42 - 60 minutes
Metabolism
The drug is metabolized via the cholinesterase and is also metabolized by microsomal enzymes in the liver
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.1178 micromolar/kg/day
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.74 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 100 mg/mL
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Formula
C12H19N2O2+
PubChem CID
4456
Canonical SMILES
CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C
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
InChIKey
ALWKGYPQUAPLQC-UHFFFAOYSA-N
CAS Number
CAS 59-99-4
ChEBI ID
CHEBI:7514
TTD Drug ID
D08USJ
DrugBank ID
DB01400
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Anisodamine      Solanaceae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression JAK-2  Molecule Info 
Pathway MAP
Up-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vivo Model SD rats (250-270 g), C57BL/6 mice (25-30 g), and rabbits (2-3 kg) CS models were used in this study.
                    Experimental
                    Result(s)		 Ani/Neo combination could produce therapeutic effects in CS.
Target and Pathway
Target(s) Acetylcholinesterase (AChE)  Molecule Info  [3]
KEGG Pathway Glycerophospholipid metabolism Click to Show/Hide
2 Cholinergic synapse
Panther Pathway Muscarinic acetylcholine receptor 1 and 3 signaling pathway Click to Show/Hide
2 Muscarinic acetylcholine receptor 2 and 4 signaling pathway
3 Nicotinic acetylcholine receptor signaling pathway
Pathwhiz Pathway Phospholipid Biosynthesis Click to Show/Hide
Pathway Interaction Database ATF-2 transcription factor network Click to Show/Hide
WikiPathways Monoamine Transport Click to Show/Hide
2 Biogenic Amine Synthesis
3 Acetylcholine Synthesis
4 Integrated Pancreatic Cancer Pathway
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Combined administration of anisodamine and neostigmine rescued acute lethal crush syndrome through Alpha7nAChR-dependent JAK2-STAT3 signaling. Sci Rep. 2016 Nov 22;6:37709.
Reference 3 Screening of acetylcholinesterase inhibitors by CE after enzymatic reaction at capillary inlet. J Sep Sci. 2009 May;32(10):1748-56.
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