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Compound Detail

CHEMBL500

PINDOLOL
💊 Approved Drug
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💊 Approved Drug
CC(C)NCC(O)COc1cccc2[nH]ccc12

Basic Information

ChEMBL ID CHEMBL500
Name PINDOLOL
Phase Approved
Structure Type MOL
InChI Key JZQKKSLKJUAGIC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

(+/-)-LB-46 (rs)-pindolol Apo-pindol Betadren Betapindol Blocklin-l Calvisken Carvisken Decreten Dl-lb-46 Dl-pindolol Durapindol +10 more
15
Targets
39
Activities
4
Assay Types
20
PK Parameters
20
Publications
22
Known Names
3
Indications
2
Mechanisms

Molecular Properties

248.3
MW (Da)
1.91
ALogP
3
HBA
3
HBD
57.3
PSA (Ų)
0.73
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -olol
USAN Year 1970

Extended Properties

Molecular Formula C14H20N2O2
MW 248.33
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.38

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Beta-1 adrenergic receptor partial agonist PARTIAL AGONIST Beta-1 adrenergic receptor
Beta-2 adrenergic receptor partial agonist PARTIAL AGONIST Beta-2 adrenergic receptor

Indications

Cardiovascular Diseases Depressive Disorder Depressive Disorder, Major

ATC Classification

C07AA03
pindolol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: BETA BLOCKING AGENTS

Activity Summary

Ki 27 meas. best 9.49
Kd 6 meas. best 9.27
IC50 5 meas. best 9.26
EC50 1 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
Ki 9.49 9.155 0.3 4
Beta-1 adrenergic receptor
CHEMBL213
Ki 9.28 9.275 0.5 2
Beta-2 adrenergic receptor
CHEMBL210
Kd 9.27 9.225 0.5 2
Beta-2 adrenergic receptor
CHEMBL210
IC50 9.26 8.96 0.5 2
Beta-1 adrenergic receptor
CHEMBL213
IC50 9.04 9.04 0.9 1
Unchecked
CHEMBL612545
Ki 9.0 9.0 1.0 2
Beta-1 adrenergic receptor
CHEMBL213
Kd 8.62 8.6 2.4 2
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 7.7 7.6433 20.0 3
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 7.65 7.226 22.4 5
5-hydroxytryptamine receptor 1A
CHEMBL214
EC50 7.57 7.57 27.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 7.32 7.32 48.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Kd 7.2 7.2 63.1 1
Beta-3 adrenergic receptor
CHEMBL246
Ki 7.18 7.18 66.0 1
5-hydroxytryptamine receptor 1B
CHEMBL3459
Ki 7.1 7.1 80.0 1
Beta-3 adrenergic receptor
CHEMBL246
IC50 7.06 7.06 88.0 1
Serotonin 1 (5-HT1) receptor
CHEMBL2095159
Ki 7.0 7.0 100.0 1
Beta-3 adrenergic receptor
CHEMBL246
Kd 6.78 6.78 166.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.0 6.0 994.5 1
D(4) dopamine receptor
CHEMBL219
Ki 5.78 5.78 1661.9 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 5.58 5.58 2600.0 1
Sigma intracellular receptor 2
CHEMBL4105907
Ki 5.48 5.48 3315.1 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 5.15 5.15 7048.6 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 4.53 4.53 29500.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 4.27 4.27 54000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.2 mL.min-1.kg-1 Homo sapiens
CL 7.7 mL.min-1.kg-1 Homo sapiens
CL 3.8 mL.min-1.kg-1 Homo sapiens
CL 7.7 mL.min-1.kg-1 Homo sapiens
CL 7.7 mL.min-1.kg-1 Homo sapiens
CL 7.59 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 79.0 % Homo sapiens
F 92.0 % Homo sapiens
Fu 0.58 - Homo sapiens
Fu 0.58 - Homo sapiens
Fu 0.58 - Homo sapiens
Fu 0.43 - Rattus norvegicus
Fu 0.4 - Rattus norvegicus
MRT 2.6 hr Homo sapiens
T1/2 2.2 hr Homo sapiens
T1/2 3.0 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Vd 7.2 L.kg-1 Rattus norvegicus
Vd 2.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor Ki = 0.32 nM 9.49 Binding affinity to human beta 2 adrenergic receptor assessed as inhibition cons... 38516587
Beta-2 adrenergic receptor Ki = 0.377 nM 9.42 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-2 adrenergic receptor Ki = 0.4 nM 9.4 Binding affinity at human adrenergic beta2 receptor 17804228
Beta-1 adrenergic receptor Ki = 0.52 nM 9.28 Binding affinity at human adrenergic beta-1 receptor 17804228
Beta-2 adrenergic receptor Kd = 0.537 nM 9.27 Displacement of [3H]-CGP 12177 from human beta-2 adrenergic receptor expressed i... 21870877
Beta-1 adrenergic receptor Ki = 0.532 nM 9.27 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Beta-2 adrenergic receptor IC50 = 0.549 nM 9.26 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Beta-2 adrenergic receptor Kd = 0.6607 nM 9.18 Antagonist activity at human beta-2 adrenergic receptor expressed in salbutamol-... 21870877
Beta-1 adrenergic receptor IC50 = 0.921 nM 9.04 DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) -
Unchecked Ki = 1.0 nM 9.0 In vitro for binding affinity against beta adrenergic receptor in rat cerebellum 2874227
Unchecked Ki = 1.0 nM 9.0 In vitro for binding affinity against beta adrenergic receptor in rat cortex 2874227
Beta-2 adrenergic receptor IC50 = 2.192 nM 8.66 GPCR PRESTO-Tango dose-response in antagonist mode with target: ADRB2 -
Beta-1 adrenergic receptor Kd = 2.399 nM 8.62 Antagonist activity at human beta-1 adrenergic receptor site 1 expressed in cime... 21870877
Beta-1 adrenergic receptor Kd = 2.63 nM 8.58 Displacement of [3H]-CGP 12177 from human beta-1 adrenergic receptor expressed i... 21870877
Beta-2 adrenergic receptor Ki = 4.91 nM 8.31 PDSP Secondary Binding target: ADRB2 - Compounds are tested at 10 uM concentrati... -
5-hydroxytryptamine receptor 1A Ki = 20.0 nM 7.7 Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox... 3543362
5-hydroxytryptamine receptor 1A Ki = 21.88 nM 7.66 Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) r... 8568799
5-hydroxytryptamine receptor 1A Ki = 22.4 nM 7.65 Displacement of [3H]DPAT from human 5HT1A receptor 17804228
5-hydroxytryptamine receptor 1A Ki = 24.0 nM 7.62 Displacement of specific [3H]- 5-HT binding to cloned human 5-hydroxytryptamine ... 10576696
5-hydroxytryptamine receptor 1A EC50 = 27.0 nM 7.57 Stimulation of [35S]- GIPyS binding to cloned human 5-hydroxytryptamine 1A recep... 10576696

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21093118 10.1016/j.ejmech.2010.10.026 Mus musculus 10
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL5058564 HEK-293T 6
- 10.6019/CHEMBL5058564 U2OS 6
19397318 10.1021/jm9003945 No relevant target 5
20869876 10.1016/j.bmc.2010.08.052 Albumin 5
15658873 10.1021/jm049711o ADMET 5
- 10.6019/CHEMBL5058564 Fibroblast 5
18426954 10.1124/dmd.108.020479 ADMET 4
19764786 10.1021/jm901036q Plasma 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
20879794 10.1021/jf102525e No relevant target 4
21870877 10.1021/jm2008562 Beta-1 adrenergic receptor 4
21870877 10.1021/jm2008562 Beta-2 adrenergic receptor 3
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 3
21870877 10.1021/jm2008562 Beta-3 adrenergic receptor 3

Data from ChEMBL 36 via Core Engine