Umeclidinium bromideProduct ingredient for Umeclidinium
- Name
- Umeclidinium bromide
- Drug Entry
- Umeclidinium
Umeclidinium is a long-acting muscarinic antagonist (LAMA) used as a maintenance treatment for symptoms of chronic obstructive pulmonary disease (COPD). COPD is a progressive obstructive lung disease characterized by shortness of breath, cough, sputum production, and chronically poor airflow with a forced expiratory volume in 1 second (FEV1) of less than 80%.3
Maintenance of the airway is controlled by the parasympathetic nervous system, particularly by the abundance of the muscarinic subtype 3 (M3) in the airway smooth muscle.5 Parasympathetic ganglia are associated with the larger airways while postganglionic fibers innervate the smaller diameter bronchioles contributing to airway resistance.5 By blocking the M3 muscarinic receptor, umeclidinium inhibits the binding of acetylcholine and thereby opens up the airways by preventing bronchoconstriction.5 However, even though umeclidinium monotherapy is well-tolerated for up to 14 days, it is more likely to be used in combination therapy, as the international Gold Initiative for Chronic Obstructive Lung Disease (GOLD) guidelines recommended the use of two long-acting bronchodilators with differing mechanisms of action to maximize efficacy and minimize adverse effects.4,2
Umeclidinium was approved by the FDA in April 2014 under the brand name Incruse Ellipta as a standalone product.14 Later, it was further approved as a combination product with vilanterol and vilanterol/fluticasone furoate under the brand name ANORO ELLIPTA and TRELEGY ELLIPTA respectively.9,10. ANORO ELLIPTA was approved in December 2013 while TRELEGY ELLIPTA was approved in September 2017.15,16
- Accession Number
- DBSALT001113
- Structure
- Synonyms
- Not Available
- UNII
- 7AN603V4JV
- CAS Number
- 869113-09-7
- Weight
- Average: 508.5
Monoisotopic: 507.177292 - Chemical Formula
- C29H34BrNO2
- InChI Key
- PEJHHXHHNGORMP-UHFFFAOYSA-M
- 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
- IUPAC Name
- 1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyclo[2.2.2]octan-1-ium bromide
- SMILES
- [Br-].OC(C1=CC=CC=C1)(C1=CC=CC=C1)C12CC[N+](CCOCC3=CC=CC=C3)(CC1)CC2
- External Links
- ChemSpider
- 9693857
- ChEBI
- 79040
- ChEMBL
- CHEMBL523299
- Wikipedia
- Umeclidinium_bromide
- Predicted Properties
Property Value Source Water Solubility 2.25e-05 mg/mL ALOGPS logP 2.2 ALOGPS logP 0.68 Chemaxon logS -7.4 ALOGPS pKa (Strongest Acidic) 13.04 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.46 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 141.75 m3·mol-1 Chemaxon Polarizability 50.56 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon