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

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.

✖

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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
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
Click here for help

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.

✖
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
References
1. Disse B, Reichl R, Speck G, Traunecker W, Ludwig Rominger KL, Hammer R. (1993)
Ba 679 BR, a novel long-acting anticholinergic bronchodilator.
Life Sci, 52 (5-6): 537-44. [PMID:8441333]
2. Dowling MR, Charlton SJ. (2006)
Quantifying the association and dissociation rates of unlabelled antagonists at the muscarinic M3 receptor.
Br J Pharmacol, 148 (7): 927-37. [PMID:16847442]
3. Prat M, Fernández D, Buil MA, Crespo MI, Casals G, Ferrer M, Tort L, Castro J, Monleón JM, Gavaldà A et al.. (2009)
Discovery of novel quaternary ammonium derivatives of (3R)-quinuclidinol esters as potent and long-acting muscarinic antagonists with potential for minimal systemic exposure after inhaled administration: identification of (3R)-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (aclidinium bromide).
J Med Chem, 52 (16): 5076-92. [PMID:19653626]
4. Sykes DA, Dowling MR, Leighton-Davies J, Kent TC, Fawcett L, Renard E, Trifilieff A, Charlton SJ. (2012)
The Influence of receptor kinetics on the onset and duration of action and the therapeutic index of NVA237 and tiotropium.
J Pharmacol Exp Ther, 343 (2): 520-8. [PMID:22854200]
5. Tanis SP, Plewe MB, Johnson TW, Butler SL, Dalvie D, DeLisle D, Dress KR, Hu Q, Huang B, Kuehler JE et al.. (2010)
Azaindole N-methyl hydroxamic acids as HIV-1 integrase inhibitors-II. The impact of physicochemical properties on ADME and PK.
Bioorg Med Chem Lett, 20 (24): 7429-34. [PMID:21036042]