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tiotropium   Click here for help

GtoPdb Ligand ID: 367

Synonyms: BA-679-BR | Spiriva®
Approved drug Immunopharmacology Ligand
tiotropium is an approved drug (FDA (2004))
Compound class: Synthetic organic
Comment: 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.
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tiotropium

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 1
Rotatable bonds 5
Topological polar surface area 115.54
Molecular weight 392.1
XLogP 0.61
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 O=C(C(c1cccs1)(c1cccs1)O)OC1CC2C3C(C(C1)[N+]2(C)C)O3
Isomeric SMILES O=C(C(c1cccs1)(c1cccs1)O)OC1C[C@@H]2[C@@H]3[C@H]([C@H](C1)[N+]2(C)C)O3
InChI InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11?,12-,13+,16-,17+
InChI Key LERNTVKEWCAPOY-FPISHFTHSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (2004)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(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 Click here for help
INN number INN
6965 tiotropium bromide
Synonyms Click here for help
BA-679-BR | Spiriva®
Database Links Click here for help
Specialist databases
GPCRdb Ligand tiotropium
Other databases
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
SynPHARM 82388 (in complex with M1 receptor)
UniChem Compound Search for chemical match using the InChIKey LERNTVKEWCAPOY-FPISHFTHSA-N
UniChem Connectivity Search for chemical match using the InChIKey LERNTVKEWCAPOY-FPISHFTHSA-N
Wikipedia Tiotropium_bromide