Tiotropium bromide

Tiotropium bromide
Clinical data
Trade namesSpiriva, others
AHFS/Drugs.comMonograph
MedlinePlusa604018
License data
Pregnancy
category
Routes of
administration		By mouth, inhalation by mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability19.5% (inhalation)
MetabolismLiver 25%
(CYP2D6, CYP3A4)
Elimination half-life5–6 days
ExcretionKidney
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.234.575 Edit this at Wikidata
Chemical and physical data
FormulaC19H22BrNO4S2
Molar mass472.41 g·mol−1
3D model (JSmol)
  • 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=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+; checkY
  • Key:DQHNAVOVODVIMG-RGECMCKFSA-M checkY

  • 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 checkY
  • Key:LERNTVKEWCAPOY-FPISHFTHSA-N checkY
  (verify)

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.[10][11] Specifically it is used during periods of breathing difficulty to prevent them from getting worse, rather than to prevent them from happening.[10] It is used by inhalation through the mouth.[10] Onset typically begins within half an hour and lasts for 24 hours.[10]

Common side effects include a dry mouth, runny nose, upper respiratory tract infection, shortness of breath and headache.[10] Severe side effects may include angioedema, worsening bronchospasm, and QT prolongation.[10] Tentative evidence has not found harm during pregnancy, however, such use has not been well studied.[1] It is an anticholinergic medication and works by blocking acetylcholine action on smooth muscle.[10]

Tiotropium was patented in 1989, and approved for medical use in 2002.[12] It is on the World Health Organization's List of Essential Medicines.[13] In 2021, it was the 134th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[14][15]

  1. ^ a b "Tiotropium Use During Pregnancy". Drugs.com. Archived from the original on 31 January 2019. Retrieved 31 January 2019.
  2. ^ a b "AusPAR: Tiotropium bromide". Therapeutic Goods Administration (TGA). 29 November 2016. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  3. ^ https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=E07D6674E971FA91CA258752004228AF&agid=(PrintDetailsPublic)&actionid=1 [dead link]
  4. ^ "Tiotropium bromide". Therapeutic Goods Administration (TGA). Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  5. ^ "Spiriva 18 microgram inhalation powder, hard capsule - Summary of Product Characteristics (SmPC)". (emc). 15 January 2019. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  6. ^ "Spiriva Respimat 2.5 microgram, inhalation solution - Summary of Product Characteristics (SmPC)". (emc). 14 January 2021. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  7. ^ "Tiogiva 18 microgram, inhalation powder, hard capsule - Summary of Product Characteristics (SmPC)". (emc). 2 June 2021. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  8. ^ "Spiriva Handihaler- tiotropium bromide capsule". DailyMed. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  9. ^ "Spiriva Respimat- tiotropium bromide inhalation spray spray, metered". DailyMed. Archived from the original on 1 October 2021. Retrieved 30 September 2021.
  10. ^ a b c d e f g "Tiotropium Bromide Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 14 October 2018. Retrieved 31 January 2019.
  11. ^ British national formulary : BNF 76 (76th ed.). Pharmaceutical Press. 2018. pp. 247–248. ISBN 9780857113382.
  12. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN 9783527607495.
  13. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Tiotropium - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.