Tiotropium bromideProduct ingredient for Tiotropium

Name
Tiotropium bromide
Drug Entry
Tiotropium

Tiotropium is a long-acting, antimuscarinic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD) and asthma.1,2,3,4,5 Tiotropium acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation and bronchodilation.1,2,3,4,5

Tiotropium is more specific for the subset of muscarinic receptors commonly found in the lungs than ipratropium.1

Tiotropium was granted FDA approval on 30 January 2004.2

Accession Number
DBSALT000348
Structure
Thumb
Synonyms
Not Available
UNII
XX112XZP0J
CAS Number
136310-93-5
Weight
Average: 472.416
Monoisotopic: 471.017362224
Chemical Formula
C19H22BrNO4S2
InChI Key
DQHNAVOVODVIMG-RGECMCKFSA-M
InChI
InChI=1S/C19H22NO4S2.BrH/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;1H/q+1;/p-1/t11?,12-,13+,16-,17+;
IUPAC Name
(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 bromide
SMILES
[Br-].[H][[email protected]@]12O[[email protected]]1([H])[[email protected]]1CC(C[[email protected]@H]2[N+]1(C)C)OC(=O)C(O)(C1=CC=CS1)C1=CC=CS1
PubChem Compound
5487426
ChemSpider
21781893
ChEMBL
CHEMBL3189058
PharmGKB
PA164769056
Wikipedia
Tiotropium_bromide
Predicted Properties
PropertyValueSource
Water Solubility0.0176 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.18 m3·mol-1ChemAxon
Polarizability39.86 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon