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Details

Stereochemistry ACHIRAL
Molecular Formula C19H22NO4S2.Br
Molecular Weight 472.416
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIOTROPIUM BROMIDE ANHYDROUS

SMILES

[Br-].[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2[N+]3(C)C)OC(=O)C(O)(C4=CC=CS4)C5=CC=CS5

InChI

InChIKey=DQHNAVOVODVIMG-FOGIBKMMSA-M
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+;

HIDE SMILES / InChI

Molecular Formula C19H21NO4S2
Molecular Weight 391.504
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tiotropium is a long–acting, antimuscarinic agent, which is often referred to as an anticholinergic. It has similar affinity to the subtypes of muscarinic receptors, M1 to M5. In the airways, it exhibits pharmacological effects through inhibition of M3–receptors at the smooth muscle leading to bronchodilation. The competitive and reversible nature of antagonism was shown with human and animal origin receptors and isolated organ preparations. In preclinical in vitro as well as in vivo studies prevention of methacholine–induced bronchoconstriction effects were dose–dependent and lasted longer than 24 hours. The bronchodilation following inhalation of tiotropium is predominantly a site–specific effect. Tiotropium is a muscarinic receptor antagonist, often referred to as an antimuscarinic or anticholinergic agent. Although it does not display selectivity for specific muscarinic receptors, on topical application it acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation, thus producing a bronchodilatory effect. Tiotropium is used in the management of chronic obstructive pulmonary disease (COPD).Tiotropium bromide capsules for inhalation are co-promoted by Boehringer-Ingelheim and Pfizer under the trade name Spiriva. It is also manufactured and marketed by Cipla under trade name Tiova.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.0316 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SPIRIVA

Cmax

ValueDoseCo-administeredAnalytePopulation
10.5 pg/mL
5 μg 1 times / day steady-state, respiratory
TIOTROPIUM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
22.1 pg × h/mL
5 μg 1 times / day steady-state, respiratory
TIOTROPIUM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
25 h
5 μg single, respiratory
TIOTROPIUM plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
28%
5 μg single, respiratory
TIOTROPIUM plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose of SPIRIVA HANDIHALER (Tiotropium) is two inhalations of the powder contents of one SPIRIVA capsule, once-daily, with the HANDIHALER device. Do not take more than one dose in 24 hours. For administration of SPIRIVA HANDIHALER, a SPIRIVA capsule is placed into the center chamber of the HANDIHALER device. The SPIRIVA capsule is pierced by pressing and releasing the green piercing button on the side of the HANDIHALER device. The tiotropium formulation is dispersed into the air stream when the patient inhales through the mouthpiece
Route of Administration: Respiratory
In Vitro Use Guide
Tiotropium bromide at > 15 pg/mL inhibited IL-8 production from both BEAS-2B cells and LFs (human lung fibroblasts) after LPS stimulation.
Substance Class Chemical
Record UNII
XX112XZP0J
Record Status Validated (UNII)
Record Version