Tiotropium

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 186691-13-4 (cation)
PubChem (CID)	5487426
IUPHAR/BPS	367
DrugBank	DB01409
ChemSpider	10482095 Y
UNII	XX112XZP0J Y
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) is a long-acting, 24-hour, anticholinergic bronchodilator 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.

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.