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Compound Detail

CHEMBL1095777

INDACATEROL
💊 Approved Drug
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💊 Approved Drug
CCc1cc2c(cc1CC)CC(NC[C@H](O)c1ccc(O)c3[nH]c(=O)ccc13)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1095777
Name INDACATEROL
Phase Approved
Structure Type MOL
InChI Key QZZUEBNBZAPZLX-QFIPXVFZSA-N
Therapeutic ✓ Yes

Known Names

Indacaterol Indacterol Onbrez QAB-149 QAB149 QABI49
16
Targets
29
Activities
3
Assay Types
6
PK Parameters
20
Publications
6
Known Names
5
Indications

Molecular Properties

392.5
MW (Da)
3.15
ALogP
4
HBA
4
HBD
85.3
PSA (Ų)
0.52
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2009
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -terol
USAN Year 2008

Extended Properties

Molecular Formula C24H28N2O3
MW 392.50
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 0.35

Indications

Lung Diseases, Obstructive Asthma Heart Failure Pulmonary Disease, Chronic Obstructive Lung Diseases

ATC Classification

R03AC18
indacaterol
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

Ki 17 meas. best 7.69
EC50 7 meas. best 9.1
IC50 5 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-2 adrenergic receptor
CHEMBL210
 EC50 9.1 8.152 0.8 5
Beta-2 adrenergic receptor
CHEMBL5414
 IC50 8.1 8.1 7.9 2
Beta-2 adrenergic receptor
CHEMBL210
 Ki 7.69 7.3675 20.6 4
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.12 7.12 75.0 1
Beta-1 adrenergic receptor
CHEMBL213
 Ki 7.04 7.04 91.0 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.97 6.97 106.9 1
Beta-1 adrenergic receptor
CHEMBL213
 IC50 6.5 6.5 316.2 1
Alpha-1A adrenergic receptor
CHEMBL229
 Ki 6.45 6.45 355.6 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 6.25 6.25 568.7 1
Alpha-1D adrenergic receptor
CHEMBL223
 Ki 6.14 6.14 731.3 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.11 6.11 770.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 5.98 5.925 1048.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 5.75 5.75 1800.3 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.7 5.7 2019.5 1
Unchecked
CHEMBL612545
 EC50 5.46 5.33 3500.0 2
Alpha-1B adrenergic receptor
CHEMBL232
 Ki 5.36 5.36 4322.6 1
Serine/arginine-rich splicing factor 6
CHEMBL5169149
 IC50 4.72 4.72 19010.0 1
Cytochrome P450 1B1
CHEMBL4878
 IC50 4.23 4.23 59200.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 76.0 mL.min-1.g-1 Rattus norvegicus
CL 378.0 mL.min-1.g-1 Rattus norvegicus
CL 66.9 L/Kg Rattus norvegicus
Fu 0.043 - Homo sapiens
T1/2 7.6 hr Rattus norvegicus
T1/2 51.0 hr Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-2 adrenergic receptor EC50 = 0.79 nM 9.1 Agonist activity at beta2 adrenoceptor (unknown origin) 33213146
Beta-2 adrenergic receptor EC50 = 1.5 nM 8.82 Agonist activity at adrenergic beta2 receptor in human A431 cells assessed as el... 25065493
Beta-2 adrenergic receptor IC50 = 7.9 nM 8.1 Agonist activity at beta2 adrenergic receptor in guinea pig tracheal strip asses... 20402514
Beta-2 adrenergic receptor IC50 = 7.9 nM 8.1 Agonist activity at adrenergic beta2 receptor in electrically-stimulated Dunkin-... 25065493
Beta-2 adrenergic receptor EC50 = 11.0 nM 7.96 Agonist activity at human beta2 adrenergic receptor assessed as increase in cAMP... 20402514
Beta-2 adrenergic receptor EC50 = 15.85 nM 7.8 Agonist activity at human beta2 adrenoceptor expressed in H292 cells assessed as... 22079756
Beta-2 adrenergic receptor Ki = 20.6 nM 7.69 Displacement of [125I]iodo-(+/-)-cyanopindolol from human adrenergic beta2 recep... 25065493
Beta-2 adrenergic receptor Ki = 20.6 nM 7.69 Displacement of [3H]CGP12177 from human beta2 adrenoceptor 20655218
Beta-2 adrenergic receptor Ki = 76.0 nM 7.12 Displacement of [125I]cyanopindolol from human recombinant beta2 adrenergic rece... 20402514
Sodium-dependent dopamine transporter Ki = 75.02 nM 7.12 PDSP Secondary Binding target: SLC6A3 - Compounds are tested at 10 uM concentrat... -
Beta-2 adrenergic receptor EC50 = 83.28 nM 7.08 GPCR PRESTO-Tango dose-response in agonist mode with target: ADRB2 -
Beta-1 adrenergic receptor Ki = 91.4 nM 7.04 Displacement of [3H]CGP12177 from human beta-1 adrenoceptor 20655218
Beta-1 adrenergic receptor Ki = 91.0 nM 7.04 Displacement of [125I]iodo-(+/-)-cyanopindolol from human adrenergic beta1 recep... 25065493
Beta-2 adrenergic receptor Ki = 105.96 nM 6.97 PDSP Secondary Binding target: ADRB2 - Compounds are tested at 10 uM concentrati... -
Sigma intracellular receptor 2 Ki = 106.86 nM 6.97 PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat... -
Beta-1 adrenergic receptor IC50 = 316.23 nM 6.5 Binding affinity to beta1 adrenoceptor 22079756
Alpha-1A adrenergic receptor Ki = 355.59 nM 6.45 PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat... -
Sodium-dependent noradrenaline transporter Ki = 568.66 nM 6.25 PDSP Secondary Binding target: SLC6A2 - Compounds are tested at 10 uM concentrat... -
Alpha-1D adrenergic receptor Ki = 731.31 nM 6.14 PDSP Secondary Binding target: ADRA1D - Compounds are tested at 10 uM concentrat... -
Sodium-dependent serotonin transporter Ki = 770.02 nM 6.11 PDSP Secondary Binding target: SLC6A4 - Compounds are tested at 10 uM concentrat... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 346
- 10.6019/CHEMBL4689842 U2OS 344
- 10.6019/CHEMBL4689842 Fibroblast 344
28703592 10.1021/acs.jmedchem.7b00205 Lipid bilayer 9
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 8
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 8
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 8
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 8
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 8
- 10.6019/CHEMBL5209801 Apelin receptor 8
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 8
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 8
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 8
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 8
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 8
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 8
25065493 10.1016/j.bmcl.2014.06.014 Beta-2 adrenergic receptor 6
20402514 10.1021/jm100068m Beta-2 adrenergic receptor 6
24900851 10.1021/ml4005232 Beta-2 adrenergic receptor 4
25065493 10.1016/j.bmcl.2014.06.014 No relevant target 3

Data from ChEMBL 36 via Core Engine