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Compound Detail

CHEMBL278020

NEOSTIGMINE
💊 Approved Drug
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💊 Approved Drug
CN(C)C(=O)Oc1cccc([N+](C)(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL278020
Name NEOSTIGMINE
Phase Approved
Structure Type MOL
InChI Key ALWKGYPQUAPLQC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Miostin Neostigmine Neostigmine (cation) Neostigmine cation Neostigmine hydroxide Neostigmine ion
6
Targets
17
Activities
1
Assay Types
2
PK Parameters
20
Publications
6
Known Names
11
Indications

Molecular Properties

223.3
MW (Da)
1.94
ALogP
2
HBA
0
HBD
29.5
PSA (Ų)
0.72
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -stigmine

Extended Properties

Molecular Formula C12H19N2O2+
MW 223.30
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.26

Indications

Glaucoma Burns Headache Postoperative Nausea and Vomiting Breast Neoplasms Gastroparesis Hypospadias Kidney Diseases Obesity, Morbid Pain Postoperative Complications

ATC Classification

N07AA01
neostigmine
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS
N07AA51
neostigmine, combinations
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS
S01EB06
neostigmine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 17 meas. best 8.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL4780
 IC50 8.34 8.34 4.6 1
Acetylcholinesterase
CHEMBL4078
 IC50 7.72 5.2817 19.0 6
Cholinesterase
CHEMBL5763
 IC50 6.8 5.4275 160.0 4
Acetylcholinesterase
CHEMBL220
 IC50 5.62 5.135 2400.0 2
Cholinesterase
CHEMBL1914
 IC50 4.79 4.56 16300.0 3
Unchecked
CHEMBL612545
 IC50 4.65 4.65 22200.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.95 - Rattus norvegicus
Vd 3.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 4.6 nM 8.34 Inhibition of Torpedo californica eel AChE using acetylthiocholine/DTNB as subst... -
Acetylcholinesterase IC50 = 19.0 nM 7.72 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 38614062
Cholinesterase IC50 = 160.0 nM 6.8 Inhibition of equine BChE using acetylthiocholine chloride as substrate preincub... 36542960
Acetylcholinesterase IC50 = 2400.0 nM 5.62 Inhibition of AChE (unknown origin) using ACh chloride as substrate preincubated... 24909082
Cholinesterase IC50 = 2930.0 nM 5.53 Inhibition of equine BuChE by Ellman's method 32822761
Acetylcholinesterase IC50 = 7500.0 nM 5.12 Inhibition of electric eel AChE by Ellman's method 32822761
Cholinesterase IC50 = 8410.0 nM 5.08 Inhibition of equine serum BChE using butyrylthiocholine chloride as substrate p... 38614062
Acetylcholinesterase IC50 = 14200.0 nM 4.85 Inhibition of electric eel acetylcholinesterase using acetylthiocholine iodide a... 24681981
Cholinesterase IC50 = 16300.0 nM 4.79 Inhibition of human BChE by Ellman's method 25257911
Acetylcholinesterase IC50 = 16300.0 nM 4.79 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 31352246
Acetylcholinesterase IC50 = 22000.0 nM 4.66 Inhibition of electric eel acetylcholinesterase using acetylthiocholine iodide a... 24675179
Unchecked IC50 = 22200.0 nM 4.65 Inhibition of electric eel AChE type VI-S using acetylthiocholine iodide as subs... 24681070
Acetylcholinesterase IC50 = 22200.0 nM 4.65 Inhibition of AChE (unknown origin) 32795767
Cholinesterase IC50 = 26100.0 nM 4.58 Inhibition of human BChE using butyrylthiocholine iodide as substrate preincubat... 24681981
Acetylcholinesterase IC50 = 28300.0 nM 4.55 Inhibition of electric eel AChE by Ellman's method 25257911
Cholinesterase IC50 = 49100.0 nM 4.31 Inhibition of human BChE using butyrylthiocholine iodide as substrate preincubat... 24675179
Cholinesterase IC50 = 49600.0 nM 4.3 Inhibition of BuChE in equine serum using butyrylthiocholine chloride as substra... 24681070

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 62
21149540 10.1124/dmd.110.035998 Brain 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
36542960 10.1016/j.bmc.2022.117132 Cholinesterase 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
25257911 10.1016/j.bmc.2014.08.026 Cholinesterase 1
24909082 10.1016/j.bmcl.2014.05.040 Acetylcholinesterase 1
21149540 10.1124/dmd.110.035998 No relevant target 1
20829430 10.1093/toxsci/kfq269 Bile salt export pump 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1
24675179 10.1016/j.ejmech.2014.03.015 Acetylcholinesterase 1
24681981 10.1016/j.ejmech.2014.03.046 Cholinesterase 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
24681070 10.1016/j.ejmech.2014.03.035 Cholinesterase 1

Data from ChEMBL 36 via Core Engine