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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tiotropium

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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+
Immunopharmacology Comments
Non-specific muscarinic cholinergic receptor bronchodilator used in treatment for bronchospasm in asthma and COPD, but not targeting a bona fide molecular immune target.
Immunopharmacology Disease
Disease X-Refs Comment References
Asthma Disease Ontology: DOID:2841
OMIM: 600807
Bronchodilator used as maintenance therapy for asthma.
Chronic obstructive pulmonary disease Disease Ontology: DOID:3083
Bronchodilator used in the treatment of COPD.