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
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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+
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]