Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL3545181

TIOTROPIUM BROMIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
C[N+]1(C)[C@@H]2C[C@@H](OC(=O)C(O)(c3cccs3)c3cccs3)C[C@H]1[C@@H]1O[C@@H]12.O.[Br-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3545181
Name TIOTROPIUM BROMIDE
Phase Approved
Structure Type MOL
InChI Key MQLXPRBEAHBZTK-SEINRUQRSA-M
Therapeutic ✓ Yes
Parent Compound CHEMBL1900528
Active Moiety CHEMBL1900528

Known Names

BA 679 BR BA-679 BR BA-679-BR BA-679BR Braltus Bromure de tiotropium Bromuro de tiotropio Spiriva Spiriva respimat Tiotropium bromide Tiotropium bromide anhydrous Tiotropium bromide hydrate +1 more
13
Targets
54
Activities
4
Assay Types
26
PK Parameters
20
Publications
13
Known Names
10
Indications
1
Mechanisms

Molecular Properties

392.5
MW (Da)
2.35
ALogP
6
HBA
1
HBD
59.1
PSA (Ų)
0.49
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2004
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical
USAN Stem -ium; -trop-

Extended Properties

Molecular Formula C19H24BrNO5S2
MW 490.44
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.51

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Muscarinic acetylcholine receptor M3 antagonist ANTAGONIST Muscarinic acetylcholine receptor M3 ✓ ✓

Indications

Asthma Bronchial Spasm Bronchial Spasm Bronchitis, Chronic Emphysema Lung Diseases, Obstructive Pulmonary Disease, Chronic Obstructive Cystic Fibrosis Neoplasms Spinal Cord Injuries

ATC Classification

R03BB04
tiotropium bromide
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R03BB54
tiotropium bromide, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

Ki 37 meas. best 11.0
IC50 14 meas. best 10.5
EC50 2 meas. best 9.4
Kd 1 meas. best 10.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M3
CHEMBL245
 Ki 11.0 10.5535 0.0 17
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 10.89 9.7233 0.0 3
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 10.7 10.0383 0.0 6
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 10.58 9.745 0.0 2
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 10.5 9.746 0.0 5
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 10.5 10.0533 0.0 3
Muscarinic acetylcholine receptor M4
CHEMBL1821
 IC50 10.4 10.4 0.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 IC50 10.3 9.72 0.1 3
Unchecked
CHEMBL612545
 Kd 10.1 10.1 0.1 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
 IC50 10.0 10.0 0.1 1
Muscarinic acetylcholine receptor M2
CHEMBL309
 Ki 9.82 9.82 0.1 1
Muscarinic acetylcholine receptor M1
CHEMBL276
 Ki 9.8 9.8 0.2 1
Muscarinic acetylcholine receptor M3
CHEMBL320
 Ki 9.52 9.52 0.3 1
Muscarinic acetylcholine receptor M3
CHEMBL245
 EC50 9.4 8.82 0.4 2
Muscarinic acetylcholine receptor M3
CHEMBL5498
 IC50 9.39 9.39 0.4 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
 Ki 9.22 9.22 0.6 1
Histamine H1 receptor
CHEMBL231
 Ki 7.68 7.68 20.8 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.69 5.69 2058.7 1
Translocator protein
CHEMBL5742
 Ki 5.37 5.37 4286.5 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.g-1 Homo sapiens
CL 5.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL - - Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr -
T1/2 24.0 hr Homo sapiens
T1/2 22.83 hr Homo sapiens
T1/2 23.83 hr Homo sapiens
T1/2 13.02 hr Homo sapiens
T1/2 24.0 hr Homo sapiens
T1/2 24.0 hr Homo sapiens
T1/2 9.452 hr -
T1/2 8.0 hr Cavia porcellus
t1/2 - - Cavia porcellus
T1/2 12.5 hr Homo sapiens
T1/2 22.6 hr Homo sapiens
T1/2 20.1 hr Homo sapiens
T1/2 13.8 hr Homo sapiens
T1/2 12.4 hr Homo sapiens
T1/2 23.0 hr Homo sapiens
T1/2 31.7 hr Homo sapiens
T1/2 20.4 hr Homo sapiens
T1/2 25.4 hr Homo sapiens
T1/2 24.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M3 Ki = 0.01 nM 11.0 Antagonist activity at human M3 receptor expressed in CHO cells assessed as inhi... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01 nM 11.0 Binding affinity to human M3 R133A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01 nM 11.0 Binding affinity to human M3 K213A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01 nM 11.0 Binding affinity to human M3 K523A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01 nM 11.0 Binding affinity to human M3 D518A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M1 Ki = 0.013 nM 10.89 Displacement of [3H]-NMS from human recombinant M1 receptor expressed in CHO cel... 21870878
Muscarinic acetylcholine receptor M3 Ki = 0.01585 nM 10.8 Binding affinity to human M3 F222A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01585 nM 10.8 Binding affinity to human M3 F225A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01585 nM 10.8 Binding affinity to human M3 E220A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01585 nM 10.8 Binding affinity to wild type human M3 receptor expressed in HEK293T cells up to... 24088171
Muscarinic acetylcholine receptor M3 Ki = 0.01995 nM 10.7 Binding affinity to human M3 E228A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M2 Ki = 0.01995 nM 10.7 Binding affinity to human M2 receptor 24088171
Muscarinic acetylcholine receptor M2 Ki = 0.0215 nM 10.67 Displacement of [3H]-NMS from human recombinant M2 receptor expressed in CHO cel... 21870878
Muscarinic acetylcholine receptor M3 Ki = 0.02512 nM 10.6 Binding affinity to human M3 Q224A mutant expressed in HEK293T cells up to 24 hr... 24088171
Muscarinic acetylcholine receptor M5 Ki = 0.0266 nM 10.58 Displacement of [3H]-NMS from human recombinant M5 receptor expressed in CHO cel... 21870878
Muscarinic acetylcholine receptor M2 IC50 = 0.03162 nM 10.5 Displacement of [3H]NMS from human muscarinic M2 receptor expressed in CHO-K1 ce... 21036043
Muscarinic acetylcholine receptor M1 IC50 = 0.03162 nM 10.5 Displacement of [3H]NMS from human muscarinic M1 receptor expressed in CHO-K1 ce... 21036043
Muscarinic acetylcholine receptor M3 Ki = 0.034 nM 10.47 Displacement of [3H]-N-methyl-scopolamine from human muscarinic M3 receptor afte... 21310610
Muscarinic acetylcholine receptor M4 IC50 = 0.03981 nM 10.4 Displacement of [3H]NMS from human muscarinic M4 receptor expressed in CHO-K1 ce... 21036043
Muscarinic acetylcholine receptor M3 IC50 = 0.05012 nM 10.3 Displacement of [3H]NMS from human muscarinic M3 receptor expressed in CHO-K1 ce... 21036043

Literature References

PubMed DOI Target Context # Activities
24088171 10.1021/jm401219y Muscarinic acetylcholine receptor M3 23
21870878 10.1021/jm200884j Muscarinic acetylcholine receptor M3 9
- 10.6019/CHEMBL5058564 HEK-293T 8
- 10.6019/CHEMBL5058564 Fibroblast 8
24837158 10.1016/j.bmc.2014.04.031 Rattus norvegicus 7
- 10.6019/CHEMBL5058564 U2OS 7
32202101 10.1021/acs.jmedchem.0c00297 Muscarinic acetylcholine receptor M3 6
19653626 10.1021/jm900132z Plasma 4
24144851 10.1016/j.bmcl.2013.09.092 Cavia porcellus 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
19653626 10.1021/jm900132z Cavia porcellus 3
22047691 10.1016/j.bmcl.2011.10.002 Cavia porcellus 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
21870878 10.1021/jm200884j Muscarinic acetylcholine receptor M2 3

Data from ChEMBL 36 via Core Engine