Tiotropium bromide

Tiotropium bromide
Clinical data
Trade names	Spiriva, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604018
License data	US DailyMed: Tiotropium bromide;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth, inhalation by mouth
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	Liver 25%; (CYP2D6, CYP3A4)
Elimination half-life	5–6 days
Excretion	Kidney
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; 5487427;
IUPHAR/BPS	367;
DrugBank	DBSALT000348; DB01409;
ChemSpider	10482095 ;
UNII	XX112XZP0J; 0EB439235F ;
KEGG	D01929;
ChEBI	CHEBI:90959; CHEBI:90960;
ChEMBL	ChEMBL3545181; ChEMBL1900528;
PDB ligand	0HK (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5044281 ;
ECHA InfoCard	100.234.575
Chemical and physical data
Formula	C19H22BrNO4S2
Molar mass	472.41 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
	SMILES C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.[Br-]; ; C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C;
	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+; ; Key:DQHNAVOVODVIMG-RGECMCKFSA-M ; ; 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 ; Key:LERNTVKEWCAPOY-FPISHFTHSA-N ;
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Tiotropium bromide, sold under the brand name Spiriva among others, is a long-acting bronchodilator (LAMA: long acting muscarinic antagonist) used in the management of chronic obstructive pulmonary disease (COPD) and asthma. Specifically it is used during periods of breathing difficulty to prevent them from getting worse, rather than to prevent them from happening. It is used by inhalation through the mouth. Onset typically begins within half an hour and lasts for 24 hours.

Common side effects include a dry mouth, runny nose, upper respiratory tract infection, shortness of breath and headache. Severe side effects may include angioedema, worsening bronchospasm, and QT prolongation. Tentative evidence has not found harm during pregnancy, however, such use has not been well studied. It is an anticholinergic medication and works by blocking acetylcholine action on smooth muscle.

Tiotropium was patented in 1989, and approved for medical use in 2002. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 154th most commonly prescribed medication in the United States, with more than 3 million prescriptions.