Tiotropium bromide

Tiotropium

Clinical data
MedlinePlus	a604018
Pregnancy category	AU: B1
Routes of administration	Inhalation (oral)
ATC code	R03BB04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	19.5% (inhalation)
Metabolism	Hepatic 25% (CYP2D6, CYP3A4)
Biological half-life	5–6 days
Excretion	Renal
Identifiers
IUPAC name (1α,2β,4β,7β)- 7-[(hydroxidi-2-thienylacetyl)oxy]-9,9-dimethyl- 3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide
CAS Number	136310-93-5
PubChem CID	5487426
IUPHAR/BPS	367
DrugBank	DB01409
ChemSpider	10482095 Y
UNII	XX112XZP0J
ChEMBL	CHEMBL1201307
ECHA InfoCard	100.234.575
Chemical and physical data
Formula	C19H22BrNO4S2
Molar mass	472.416 g/mol
3D model (Jmol)	Interactive image
SMILES C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.[Br-]
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-/m0/s1 Y Key:LERNTVKEWCAPOY-MCGYIYAPSA-N Y

Tiotropium bromide (INN) (originally marketed as Spiriva) is a long-acting, 24-hour, anticholinergic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD).

Tiotroprium was discovered in 1991 and came to market in 2004.

Tiotropium is used for maintenance treatment of chronic obstructive pulmonary disease (COPD) which includes chronic bronchitis and emphysema. It is not however used for acute exacerbations.

Adverse effects are mainly related to its antimuscarinic effects. Common adverse drug reactions (≥1% of patients) associated with tiotropium therapy include: dry mouth and/or throat irritation. Rarely (<0.1% of patients) treatment is associated with:urinary retention, constipation, acute angle closure glaucoma, palpitations (notably supraventricular tachycardia and atrial fibrillation) and/or allergy (rash, angioedema, anaphylaxis).

Tiotropium and another member of its class ipratropium were linked to increased risk of heart attacks, stroke and cardiovascular death. The FDA requested further trials; these are now complete, and adequately resolve the previous safety concerns.

Tiotropium mist inhaler (Respimat) has been found to be associated with an increase of all cause mortality in people with COPD.

The standard dose of tiotropium is 18 mcg which is administered by a HandiHaler inhalation device.

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, when topically applied it acts mainly on M₃ muscarinic receptors located on smooth muscle cells and submucosal glands. This leads to a reduction in smooth muscle contraction and mucus secretion and thus produces a bronchodilatory effect.