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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View more information in the IUPHAR Pharmacology Education Project: tiotropium

2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
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 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
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