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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL278020
CHEMBL278020
Compound Name NEOSTIGMINE
ChEMBL Synonyms NEOSTIGMINE | NEOSTIGMINE METHYLSULFATE | PROSTIGMINE | Neostigmine bromide
Max Phase 4 (Approved)
Trade Names PROSTIGMINE
Molecular Formula C12H19N2O2

Additional synonyms for CHEMBL278020 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C
Standard InChI InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4 ...
Download InChI
Standard InChI Key ALWKGYPQUAPLQC-UHFFFAOYSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL278020

Molecule Features

CHEMBL278020 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Acetylcholinesterase inhibitor Acetylcholinesterase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
MYASTHENIA GRAVISD009157EFO:0004991MYASTHENIA GRAVIS4DailyMed
DailyMed

Clinical Data

ClinicalTrials.gov NEOSTIGMINE
The Cochrane Collaboration NEOSTIGMINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL278020. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL220 Acetylcholinesterase Homo sapiens 1.000
CHEMBL3403 Butyrylcholinesterase Rattus norvegicus 1.000
CHEMBL5077 Butyrylcholinesterase Equus caballus 0.999
CHEMBL5932 LIM domain kinase 2 Homo sapiens 0.997
CHEMBL1914 Butyrylcholinesterase Homo sapiens 0.995
CHEMBL4780 Acetylcholinesterase Torpedo californica 0.989
CHEMBL3199 Acetylcholinesterase Rattus norvegicus 0.979
CHEMBL1906 Serine/threonine-protein kinase RAF Homo sapiens 0.937
CHEMBL4768 Acetylcholinesterase Bos taurus 0.825
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.626
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.247
CHEMBL4191 Monoglyceride lipase Homo sapiens 0.225



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL220 Acetylcholinesterase Homo sapiens 1.000
CHEMBL5077 Butyrylcholinesterase Equus caballus 1.000
CHEMBL1914 Butyrylcholinesterase Homo sapiens 0.999
CHEMBL3403 Butyrylcholinesterase Rattus norvegicus 0.999
CHEMBL4768 Acetylcholinesterase Bos taurus 0.999
CHEMBL4780 Acetylcholinesterase Torpedo californica 0.997
CHEMBL3199 Acetylcholinesterase Rattus norvegicus 0.993
CHEMBL5932 LIM domain kinase 2 Homo sapiens 0.991
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.798
CHEMBL1906 Serine/threonine-protein kinase RAF Homo sapiens 0.755
CHEMBL3587 Dual specificity mitogen-activated protein kinase kinase 1 Homo sapiens 0.431
CHEMBL4191 Monoglyceride lipase Homo sapiens 0.349
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.334
CHEMBL5763 Cholinesterase Equus caballus 0.256

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
223.3 223.1447 0.51 3 29.54 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 0 0 4 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - -2.09 -2.09 1 16 0.7

Structural Alerts

There are 3 structural alerts for CHEMBL278020. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01E - ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01EB - Parasympathomimetics
S01EB06 - neostigmine

N - NERVOUS SYSTEM
N07 - OTHER NERVOUS SYSTEM DRUGS
N07A - PARASYMPATHOMIMETICS
N07AA - Anticholinesterases
N07AA01 - neostigmine

N - NERVOUS SYSTEM
N07 - OTHER NERVOUS SYSTEM DRUGS
N07A - PARASYMPATHOMIMETICS
N07AA - Anticholinesterases
N07AA51 - neostigmine, combinations

ChemSpider ChemSpider:ALWKGYPQUAPLQC-UHFFFAOYSA-N
DailyMed neostigmine methylsulfate
PubChem SID: 11111527 SID: 11111528 SID: 26756597 SID: 90340848

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL278020



ACToR 59-99-4
BindingDB 50022775
Brenda 47472 2571 30362
ChEBI 7514
DrugBank DB01400
DrugCentral 1897
eMolecules 31796384
EPA CompTox Dashboard DTXSID1023360
FDA SRS 3982TWQ96G
Guide to Pharmacology 8993
Human Metabolome Database HMDB0015472
IBM Patent System 27B30F2650E26BCEDD06474052ACED3B
KEGG Ligand C07258
LINCS LSM-5360
Mcule MCULE-3501840981
Nikkaji J4.797J
NMRShiftDB 20200212
PharmGKB PA450611
PubChem 4456
PubChem: Thomson Pharma 15121488
SureChEMBL SCHEMBL34419
ZINC ZINC000000001792

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/ALWKGYPQUAPLQC-UHFFFAOYSA-N spacer
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