Umeclidinium bromide

Umeclidinium bromide, sold under the brand name Incruse Ellipta, is a long-acting muscarinic antagonist approved for the maintenance treatment of chronic obstructive pulmonary disease (COPD).^[3] It is also approved for this indication in combination with vilanterol (as umeclidinium bromide/vilanterol)^[4][5] and also as a triple-therapy combination as fluticasone furoate/umeclidinium bromide/vilanterol.^[6]

Umeclidinium bromide

Clinical data
Trade names	Incruse Ellipta
Other names	GSK573719A
License data	US DailyMed: Umeclidinium bromide
Routes of administration	Inhalation (DPI)
ATC code	R03BB07 (WHO) R03AL03 (WHO) (+vilanterol)
Legal status
Legal status	AU: S4 (Prescription only)[1] CA: ℞-only[2] UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	~89%[3]
Metabolism	Liver (CYP2D6)
Elimination half-life	11 hours
Excretion	Feces (58%) and urine (22%)
Identifiers
IUPAC name Diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol bromide
CAS Number	869113-09-7
PubChem CID	11519069
DrugBank	DB09076
ChemSpider	9693857
UNII	7AN603V4JV
KEGG	D10181
ChEBI	CHEBI:79040
CompTox Dashboard (EPA)	DTXSID50235966
ECHA InfoCard	100.166.375
Chemical and physical data
Formula	C29H34BrNO2
Molar mass	508.500 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccccc3)(CC1)CC2.[Br-]
InChI InChI=1S/C29H34NO2.BrH/c31-29(26-12-6-2-7-13-26,27-14-8-3-9-15-27)28-16-19-30(20-17-28,21-18-28)22-23-32-24-25-10-4-1-5-11-25;/h1-15,31H,16-24H2;1H/q+1;/p-1 Key:PEJHHXHHNGORMP-UHFFFAOYSA-M

It is on the World Health Organization's List of Essential Medicines.^[7] In 2020, it was the 245th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[8][9]

References

1. "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
2. "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
3. "Incruse Ellipta (umeclidinium inhalation powder) for Oral Inhalation Use. Full Prescribing Information" (PDF). GlaxoSmithKline, Research Triangle Park, NC 27709. Archived from the original (PDF) on 10 July 2018. Retrieved 22 February 2016.
4. Feldman GJ, Edin A (December 2013). "The combination of umeclidinium bromide and vilanterol in the management of chronic obstructive pulmonary disease: current evidence and future prospects". Therapeutic Advances in Respiratory Disease. 7 (6): 311–9. doi:10.1177/1753465813499789. PMID 24004659. S2CID 5744282.
5. "FDA Approves Umeclidinium and Vilanterol Combo for COPD". Medscape. December 18, 2013.
6. "TRELEGY ELLIPTA Package Insert" (PDF). GlaxoSmithKline. September 2017. Retrieved 11 July 2020.
7. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
8. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
9. "Umeclidinium - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.