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Compound Detail

CHEMBL499

TIMOLOL
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)NC[C@H](O)COc1nsnc1N1CCOCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL499
Name TIMOLOL
Phase Approved
Structure Type MOL
InChI Key BLJRIMJGRPQVNF-JTQLQIEISA-N
Therapeutic ✓ Yes

Known Names

Betim Betimol Blocadren Glau-opt Glaucol Nyogel Timolol Timolol anhydrous Timolol hemihydrate Tiopex
11
Targets
30
Activities
4
Assay Types
17
PK Parameters
20
Publications
10
Known Names
15
Indications
2
Mechanisms

Molecular Properties

316.4
MW (Da)
0.50
ALogP
8
HBA
2
HBD
79.7
PSA (Ų)
0.79
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1978
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Stem -olol
USAN Year 1973

Extended Properties

Molecular Formula C13H24N4O3S
MW 316.43
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -1.47

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Beta-1 adrenergic receptor antagonist ANTAGONIST Beta-1 adrenergic receptor ✓ ✓
Beta-2 adrenergic receptor antagonist ANTAGONIST Beta-2 adrenergic receptor ✓ ✓

Indications

Cardiovascular Diseases Glaucoma Glaucoma, Open-Angle Ocular Hypertension Exfoliation Syndrome Melanoma Paronychia Hemangioma Macular Degeneration Migraine Disorders Telangiectasia, Hereditary Hemorrhagic Varicose Ulcer Wet Macular Degeneration Wounds and Injuries Sturge-Weber Syndrome

ATC Classification

C07AA06
timolol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: BETA BLOCKING AGENTS
S01ED01
timolol
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01ED51
timolol, combinations
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 16 meas. best 9.7
IC50 6 meas. best 9.67
Kd 6 meas. best 9.78
EC50 2 meas. best 4.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL5414
 Kd 9.78 9.6733 0.2 3
Beta-2 adrenergic receptor
CHEMBL210
 Ki 9.7 9.37 0.2 3
Beta-2 adrenergic receptor
CHEMBL210
 IC50 9.67 9.605 0.2 2
Beta-1 adrenergic receptor
CHEMBL5471
 Kd 9.44 9.44 0.4 3
Beta-1 adrenergic receptor
CHEMBL213
 Ki 8.82 8.4367 1.5 3
Beta-1 adrenergic receptor
CHEMBL213
 IC50 8.59 8.59 2.6 1
Beta-1 adrenergic receptor
CHEMBL3252
 Ki 8.5 7.62 3.2 5
Beta-3 adrenergic receptor
CHEMBL246
 Ki 6.47 6.47 339.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.41 6.41 391.2 1
Beta-3 adrenergic receptor
CHEMBL246
 IC50 6.34 6.34 452.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 6.21 6.01 616.6 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 IC50 5.57 5.57 2712.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 5.28 5.28 5280.8 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.96 4.96 11000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 4.54 4.49 28800.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 9.17 mL.min-1.kg-1 Homo sapiens
CL 8.5 mL.min-1.kg-1 Homo sapiens
CL 7.1 mL.min-1.kg-1 Homo sapiens
CL 8.5 mL.min-1.kg-1 Homo sapiens
CL 8.5 mL.min-1.kg-1 Homo sapiens
CL 48.9 mL.min-1.kg-1 Homo sapiens
CL 8.1 uL.min-1.(10^6cells)-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
F 50.0 % Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.9 - Homo sapiens
Fu 0.48 - Not specified
Fu 0.988 - Homo sapiens
MRT 3.0 hr Homo sapiens
T1/2 2.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Kd = 0.166 nM 9.78 In vitro inhibitory activity against beta-2 adrenoceptor was measured by the inh... 2872332
Beta-2 adrenergic receptor Ki = 0.201 nM 9.7 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-2 adrenergic receptor Ki = 0.2089 nM 9.68 Displacement of [3H]-CGP12177 from human beta2 ADR expressed in HEK293T cell mem... 29851481
Beta-2 adrenergic receptor IC50 = 0.2153 nM 9.67 GPCR PRESTO-Tango dose-response in antagonist mode with target: ADRB2 -
Beta-2 adrenergic receptor Kd = 0.2399 nM 9.62 Beta-2 adrenergic receptor antagonistic activity on guinea pig tracheal chains 6126588
Beta-2 adrenergic receptor Kd = 0.2399 nM 9.62 In vitro beta-2 adrenergic receptor activity was determined by measuring inhibit... 6134834
Beta-2 adrenergic receptor IC50 = 0.292 nM 9.54 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-1 adrenergic receptor Kd = 0.3631 nM 9.44 In vitro inhibitory activity against beta-1 adrenergic receptor measured by inhi... 2872332
Beta-1 adrenergic receptor Kd = 0.3631 nM 9.44 In vitro beta-1 adrenergic receptor activity was determined via inhibition of th... 6134834
Beta-1 adrenergic receptor Kd = 0.3631 nM 9.44 Compound was tested for its Beta-1 adrenergic receptor antagonistic activity on ... 6126588
Beta-1 adrenergic receptor Ki = 1.503 nM 8.82 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-2 adrenergic receptor Ki = 1.863 nM 8.73 PDSP Secondary Binding target: ADRB2 - Compounds are tested at 10 uM concentrati... -
Beta-1 adrenergic receptor IC50 = 2.603 nM 8.59 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-1 adrenergic receptor Ki = 3.162 nM 8.5 Antagonist activity at rat wild type beta-1 adrenergic receptor expressed in CHO... 16759089
Beta-1 adrenergic receptor Ki = 5.37 nM 8.27 Displacement of [3H]-CGP12177 from human beta1 ADR expressed in HEK293T cell mem... 29851481
Beta-1 adrenergic receptor Ki = 6.016 nM 8.22 PDSP Secondary Binding target: ADRB1 - Compounds are tested at 10 uM concentrati... -
Beta-1 adrenergic receptor Ki = 7.943 nM 8.1 Antagonist activity at rat beta-1 adrenergic receptor W134A mutant expressed in ... 16759089
Beta-1 adrenergic receptor Ki = 15.85 nM 7.8 Antagonist activity at rat beta-1 adrenergic receptor Y356F mutant expressed in ... 16759089
Beta-1 adrenergic receptor Ki = 31.62 nM 7.5 Antagonist activity at rat beta-1 adrenergic receptor S190A mutant expressed in ... 16759089
Beta-3 adrenergic receptor Ki = 339.0 nM 6.47 DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 498
- 10.6019/CHEMBL4689842 Fibroblast 346
- 10.6019/CHEMBL4689842 HEK-293T 346
- 10.6019/CHEMBL4689842 U2OS 344
- 10.5281/zenodo.13943903 ADMET 89
2891852 10.1021/jm00396a015 Oryctolagus cuniculus 36
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
1635066 10.1021/jm00092a021 Oryctolagus cuniculus 10
20070106 10.1021/jm901371v Homo sapiens 8
29851481 10.1021/acs.jmedchem.8b00625 Oryctolagus cuniculus 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
19397318 10.1021/jm9003945 No relevant target 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
28687205 10.1016/j.bmcl.2017.06.065 Oryctolagus cuniculus 5

Data from ChEMBL 36 via Core Engine