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Compound Detail

CHEMBL1201237

LEVOBUNOLOL
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)NC[C@H](O)COc1cccc2c1CCCC2=O

Basic Information

ChEMBL ID CHEMBL1201237
Name LEVOBUNOLOL
Phase Approved
Structure Type MOL
InChI Key IXHBTMCLRNMKHZ-LBPRGKRZSA-N
Therapeutic ✓ Yes

Known Names

Bunolol, (-)- Bunolol, (s)- Levobunolol
6
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

291.4
MW (Da)
2.33
ALogP
4
HBA
2
HBD
58.6
PSA (Ų)
0.87
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -olol
USAN Year 1979

Extended Properties

Molecular Formula C17H25NO3
MW 291.39
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.32

Indications

Glaucoma

ATC Classification

S01ED03
levobunolol
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 6 meas. best 9.1
Ki 6 meas. best 9.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
Ki 9.26 9.26 0.5 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 9.1 9.1 0.8 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 8.4 8.4 4.0 1
Beta-1 adrenergic receptor
CHEMBL213
IC50 8.16 8.16 6.9 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 6.59 6.59 255.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.49 6.49 325.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 6.47 6.47 340.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.11 6.11 773.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.78 5.78 1658.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.58 5.58 2602.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 5.54 5.54 2901.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.31 5.31 4898.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Ki = 0.546 nM 9.26 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-2 adrenergic receptor IC50 = 0.793 nM 9.1 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-1 adrenergic receptor Ki = 3.985 nM 8.4 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-1 adrenergic receptor IC50 = 6.9 nM 8.16 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-3 adrenergic receptor Ki = 255.0 nM 6.59 DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) -
Sigma non-opioid intracellular receptor 1 Ki = 325.0 nM 6.49 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Beta-3 adrenergic receptor IC50 = 340.0 nM 6.47 DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) -
Sigma non-opioid intracellular receptor 1 IC50 = 773.0 nM 6.11 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
5-hydroxytryptamine receptor 1A Ki = 1658.0 nM 5.78 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter Ki = 2602.0 nM 5.58 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 1A IC50 = 2901.0 nM 5.54 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter IC50 = 4898.0 nM 5.31 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.1016/S0960-894X(97)00046-2 ADMET 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 Vascular endothelial growth factor receptor 2 1
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 1
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 1
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1

Data from ChEMBL 36 via Core Engine