olodaterol   Click here for help

GtoPdb Ligand ID: 7543

Synonyms: BI-1744 | BI-1744-CL | Striverdi®
Approved drug PDB Ligand Immunopharmacology Ligand
olodaterol is an approved drug (FDA (2014))
Compound class: Synthetic organic
Comment: Marketed formulations may contain olodaterol hydrochloride (PubChem CID 11711522).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: olodaterol

olodaterol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 100.05
Molecular weight 386.18
XLogP 1.81
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccc(cc1)CC(NCC(c1cc(O)cc2c1OCC(=O)N2)O)(C)C
Isomeric SMILES COc1ccc(cc1)CC(NC[C@@H](c1cc(O)cc2c1OCC(=O)N2)O)(C)C
InChI InChI=1S/C21H26N2O5/c1-21(2,10-13-4-6-15(27-3)7-5-13)22-11-18(25)16-8-14(24)9-17-20(16)28-12-19(26)23-17/h4-9,18,22,24-25H,10-12H2,1-3H3,(H,23,26)/t18-/m0/s1
InChI Key COUYJEVMBVSIHV-SFHVURJKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Olodaterol was approved by the FDA in July 2014 as an inhalation medication for the treatment of chronic obstructive pulmonary disease (COPD). Phase 2 trials have also been conducted in patients with asthma (see NCT01013753).
This drug has been further assessed in clinical trials in combination with the muscarinic antagonist tiotropium bromide (also a bronchodilator).
In May 2015 the US FDA approved a fixed-dose combination of tiotropium bromide and olodaterol (Stiolto Respimat®) as 'a long-term, once-daily maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema' Drugs.com.
Click here to view a full list of associated trials registered with ClinicalTrials.gov.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Olodaterol is a long acting β-adrenoceptor agonist (LABA) acting on β2-ARs in the lung to cause bronchodilation which improves airway function. Olodaterol appears to have low intrinsic β1-AR action, thereby limiting cardiac side effects [1].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01013753 A Study of the Safety and Efficacy of 4 Doses of BI 1744 CL Delivered Via the Respimat in Patients With Asthma. Phase 2 Interventional Boehringer Ingelheim
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)