tiotropium

Ligand id: 367

Name: tiotropium

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View more information in the IUPHAR Pharmacology Education Project: tiotropium

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 115.54
Molecular weight 392.1
XLogP 0.61
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

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 from GtoPdb and ChEMBL (where available) across species

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2004))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1R,2R,4S,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
International Nonproprietary Names
INN number INN
6965 tiotropium bromide
Synonyms
BA-679-BR | Spiriva®
Comments
We have chosen to display the structure of the parent compound, tiotropium, as this reflects the compound used in the experimental data listed under the 'biological activity' tab, and the links in the table above also represent the parent compound. However, the INN-assigned compound is in complex with bromide, the approved drug is also administered in this preparation. Note that the activity data in PubChem for this compound is split between the parent and the preparation with bromide.
Database Links
CAS Registry No. 186691-13-4
ChEMBL Ligand CHEMBL3305968
DrugBank Ligand DB01409
GtoPdb PubChem SID 135651266
PubChem CID 5487427
Search Google for chemical match using the InChIKey LERNTVKEWCAPOY-FPISHFTHSA-N
Search Google for chemicals with the same backbone LERNTVKEWCAPOY
Search PubMed clinical trials tiotropium bromide
Search PubMed titles tiotropium bromide
Search PubMed titles/abstracts tiotropium bromide
Search UniChem for chemical match using the InChIKey LERNTVKEWCAPOY-FPISHFTHSA-N
Search UniChem for chemicals with the same backbone LERNTVKEWCAPOY
SynPHARM 82388 (in complex with M1 receptor)
Wikipedia Tiotropium_bromide