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Compound Detail

CHEMBL221753

BENZETHONIUM CHLORIDE
🧪 Phase II
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🧪 Phase II
CC(C)(C)CC(C)(C)c1ccc(OCCOCC[N+](C)(C)Cc2ccccc2)cc1.[Cl-]

Basic Information

ChEMBL ID CHEMBL221753
Name BENZETHONIUM CHLORIDE
Phase Phase II
Structure Type MOL
InChI Key UREZNYTWGJKWBI-UHFFFAOYSA-M
Parent Compound CHEMBL1182210
Active Moiety CHEMBL1182210

Known Names

Benzethonium chloride Benzethonium chloride concentrate Chlorure de benzethonium Cloruro de bencetonio Hyamine Neostelin green NSC-20200 Phemerol Phemerol chloride
30
Targets
68
Activities
3
Assay Types
0
PK Parameters
20
Publications
9
Known Names

Molecular Properties

412.6
MW (Da)
6.07
ALogP
2
HBA
0
HBD
18.5
PSA (Ų)
0.33
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -ium; -onium

Extended Properties

Molecular Formula C27H42ClNO2
MW 448.09
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness -0.61

ATC Classification

D08AJ08
benzethonium chloride
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS
D08AJ58
benzethonium chloride, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS

Activity Summary

IC50 46 meas. best 6.96
Ki 20 meas. best 7.44
EC50 2 meas. best 5.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.44 7.44 36.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.43 7.43 37.0 1
Unchecked
CHEMBL612545
Ki 7.16 6.5125 70.0 4
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.09 7.09 81.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 7.05 7.05 88.9 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 7.02 7.02 96.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 7.0 7.0 99.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.96 6.96 108.5 1
Unchecked
CHEMBL612545
IC50 6.94 5.0671 114.0 17
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.89 6.89 129.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.87 6.87 134.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.69 6.69 204.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.59 6.59 257.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.54 6.54 285.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.53 6.53 294.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.42 6.42 383.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.38 6.38 412.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.27 6.27 538.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 6.24 6.24 574.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.19 6.19 643.0 1
Substance-K receptor
CHEMBL2327
Ki 6.19 6.19 642.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 6.12 6.12 768.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 6.05 6.05 900.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 6.04 6.04 907.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.99 5.99 1027.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.96 5.96 1085.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.93 5.93 1163.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.89 5.89 1295.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.87 5.87 1365.0 1
Unchecked
CHEMBL612545
EC50 5.78 5.7 1680.0 2
Substance-K receptor
CHEMBL2327
IC50 5.72 5.72 1925.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.71 5.71 1961.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
IC50 5.68 5.68 2084.0 1
Acetylcholinesterase
CHEMBL220
IC50 5.65 5.65 2246.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.61 5.61 2438.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.51 5.51 3102.0 1
A549
CHEMBL392
IC50 5.5 5.5 3200.0 1
KiSS-1 receptor
CHEMBL5413
Ki 5.44 5.44 3600.0 1
CCRF-CEM
CHEMBL382
IC50 5.42 5.42 3800.0 1
MDA-MB-231
CHEMBL400
IC50 5.32 5.32 4800.0 1
MCF7
CHEMBL387
IC50 5.3 5.3 5000.0 1
HeLa
CHEMBL399
IC50 5.24 5.24 5700.0 1
Candida albicans
CHEMBL366
IC50 5.06 5.06 8700.0 1
HSP60/HSP10
CHEMBL4106131
IC50 4.64 4.64 23000.0 1
Apoptotic protease-activating factor 1
CHEMBL1795093
IC50 4.63 4.63 23500.0 1
GroEL/GroES
CHEMBL4106139
IC50 4.62 4.6 24000.0 2
HUVEC
CHEMBL613979
IC50 4.33 4.33 47000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M4 Ki = 36.0 nM 7.44 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A Ki = 37.0 nM 7.43 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked Ki = 70.0 nM 7.16 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Muscarinic acetylcholine receptor M3 Ki = 81.0 nM 7.09 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Voltage-gated inwardly rectifying potassium channel KCNH2 Ki = 88.9 nM 7.05 DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole) -
Muscarinic acetylcholine receptor M5 Ki = 96.0 nM 7.02 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 99.0 nM 7.0 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 108.5 nM 6.96 DRUGMATRIX: Potassium Channel HERG radioligand binding (ligand: [3H] Astemizole) -
Unchecked IC50 = 114.0 nM 6.94 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
5-hydroxytryptamine receptor 2A IC50 = 129.0 nM 6.89 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M5 IC50 = 134.0 nM 6.87 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M2 Ki = 204.0 nM 6.69 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 232.0 nM 6.63 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Muscarinic acetylcholine receptor M4 IC50 = 257.0 nM 6.59 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked IC50 = 254.0 nM 6.59 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Alpha-2C adrenergic receptor Ki = 285.0 nM 6.54 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Alpha-2B adrenergic receptor Ki = 294.0 nM 6.53 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Muscarinic acetylcholine receptor M3 IC50 = 383.0 nM 6.42 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 IC50 = 412.0 nM 6.38 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 439.0 nM 6.36 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 627
20660673 10.1128/aac.01065-09 Staphylococcus aureus 10
22285320 10.1016/j.bmcl.2012.01.025 Escherichia coli 6
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
22285320 10.1016/j.bmcl.2012.01.025 Staphylococcus aureus 4
22285320 10.1016/j.bmcl.2012.01.025 Staphylococcus epidermidis 4
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
22285320 10.1016/j.bmcl.2012.01.025 Pseudomonas aeruginosa 4
25780985 10.1021/jm501628s Staphylococcus aureus 2
23792315 10.1016/j.ejmech.2013.05.033 A549 2
23792315 10.1016/j.ejmech.2013.05.033 CCRF-CEM 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
22285320 10.1016/j.bmcl.2012.01.025 Enterococcus faecalis 2
22285320 10.1016/j.bmcl.2012.01.025 Enterococcus faecium 2
22285320 10.1016/j.bmcl.2012.01.025 Streptococcus pneumoniae 2
17266198 10.1021/jm0609824 KiSS-1 receptor 2
22285320 10.1016/j.bmcl.2012.01.025 Stenotrophomonas maltophilia 2
22285320 10.1016/j.bmcl.2012.01.025 Acinetobacter baumannii 2
22285320 10.1016/j.bmcl.2012.01.025 Klebsiella pneumoniae 2
22285320 10.1016/j.bmcl.2012.01.025 ADMET 1

Data from ChEMBL 36 via Core Engine