Umeclidinium Bromide

Base Information

• Chemical Name: Umeclidinium Bromide
• CAS No.: 869113-09-7
• Molecular Formula: Br*C₂₉H₃₄NO₂
• Molecular Weight: 508.498
• European Community (EC) Number: 638-761-1
• UNII: 7AN603V4JV
• ChEMBL ID: CHEMBL523299
• DSSTox Substance ID: DTXSID50235966
• NCI Thesaurus Code: C152797
• RXCUI: 1487512
• Wikidata: Q15624035
• Wikipedia: Umeclidinium_bromide
• Mol file: 869113-09-7.mol

Synonyms:Umeclidinium bromide;869113-09-7;Incruse Ellipta;GSK573719A;Umeclidinium (bromide);Anoro Ellipta;GSK-573719A;UNII-7AN603V4JV;umeclidinii bromidum;UMEC;7AN603V4JV;bromure d'umeclidinium;bromuro de umeclidinio;1-[2-(Benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-quinuclidinium Bromide;CHEBI:79040;DTXSID50235966;GSK-573719;1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide;Diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol bromide;TRELEGY ELLIPTA COMPONENT UMECLIDINIUM BROMIDE;UMECLIDINIUM BROMIDE COMPONENT OF TRELEGY ELLIPTA;CHEMBL523299;1-(2-(Benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)-1-azoniabicyclo(2.2.2)octane bromide;1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyclo[2.2.2]octan-1-ium bromide;1-(2-((BENZYL)OXY)ETHYL)4-(HYDROXYDI(PHENYL)METHYL)-1-AZABICYCLO(2.2.2)OCTAN-1-IUM BROMIDE;incruse;Umeclidinium bromide [USAN];Umeclidinium brom;1-(2-(benzyloxy)ethyl)-4-(hydroxy(diphenyl)methyl)-1-azoniabicyclo(2.2.2)octane bromide;1-[2-(benzyloxy)ethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide;Umeclidinium bromide [USAN:INN];4-[Hydroxy(diphenyl)methyl]-1-[2-[(phenylmethyl)oxy]ethyl]-1-azoniabicyclo[2.2.2]octane bromide;4-[Hydroxy(diphenyl)methyl]-1-{2-[(phenylmethyl)oxy]ethyl}-1-azoniabicyclo[2.2.2]octane Bromide;Incruse ellipta (TN);C29H34BrNO2;SCHEMBL109931;DTXCID80158457;R03BB07;UMECLIDINIUM BROMIDE [MI];PEJHHXHHNGORMP-UHFFFAOYSA-M;Umeclidinium bromide (JAN/USAN);HMS3885A04;UMECLIDINIUM BROMIDE [INN];UMECLIDINIUM BROMIDE [JAN];BCP11148;EX-A1683;GSK 573719A;UMECLIDINIUM BROMIDE [VANDF];UMECLIDINIUM BROMIDE [WHO-DD];AKOS025404842;CCG-269761;CS-0874;SB16738;AC-30852;AS-57320;HY-12100;SY226333;UMECLIDINIUM BROMIDE [ORANGE BOOK];FT-0775078;NS00127433;D10181;A916880;EN300-18166815;Q15624035;1-[2-(Benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-quinuclidiniumBromide;1-[2-(benzyloxy)ethyl]-4(hydroxydiphenylmethyl)-1-azoniabicyclo[2.2.2]octane bromide;diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide;1-Azoniabicyclo(2.2.2)octane, 4-(hydroxydiphenylmethyl)-1-(2-(phenylmethoxy)ethyl)-, bromide (1:1);GSK-573719 pound>> GSK573719 pound>> GSK 573719 pound>>GSK573719A

Chemical Property of Umeclidinium Bromide

Chemical Property:

• PSA: 29.46000
• LogP: 2.10280
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 507.17729
• Heavy Atom Count: 33
• Complexity: 543

Purity/Quality:

99% ^*data from raw suppliers

UmeclidiniumBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C[N+]2(CCC1(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)CCOCC5=CC=CC=C5.[Br-]
• Recent ClinicalTrials: ANTES B+ Clinical Trial
• Recent EU Clinical Trials: PHASE IV, SINGLE-CENTER, DOUBLE BLIND, RANDOMIZED, CROSSOVER, PLACEBO-CONTROLLED STUDY, TO INVESTIGATE THE EFFECT OF DUAL BRONCHODILATION WITH UMECLIDINIUM VILANTEROL ON PATIENTS WITH COPD, HYPERINFLATION AND HEART FAILURE.
• Recent NIPH Clinical Trials: A comparison of the additive efficacy of Umeclidinium bromide on fluticasone furoate/vilanterole in asthma-COPD overlap syndrome.
• Description: Umeclidinium bromide is a long-acting muscarinic acetylcholine antagonist developed by GlaxoSmithKline and approved by the US FDA at the end of 2013 for use in combination with vilanterol, a b2 agonist, for the treatment of chronic obstructive pulmonary disease. Due to umeclidinium’s poor oral bioavailability, the drug is administrated by inhalation as dry powder.
• Uses: Umeclidinium Bromide is considered as a potentially long-acting antimuscarinic agent.

Technology Process of Umeclidinium Bromide

There total 23 articles about Umeclidinium Bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.01%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrochloride → Umeclidinium bromide (869113-09-7)

Guidance literature:

In propan-1-ol; water; for 2h; Solvent; Reflux;

Reference yield: 93.25%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol hydrobromide → Umeclidinium bromide (869113-09-7)

Guidance literature:

In 2-methyltetrahydrofuran; water; for 2.5h; Reflux;

Reference yield: 92.87%

bromoethyl-2-benzyl ether (1462-37-9) + (1-azabicyclo[2.2.2]octane-4-yl)(diphenyl)methanol sulfuric acid → Umeclidinium bromide (869113-09-7)

Guidance literature:

In water; acetonitrile; for 3h; Reflux;

upstream raw materials:

α,α-diphenyl-1-azabicyclo[2.2.2]octane-4-methanol

bromoethyl-2-benzyl ether

4-carbethoxypiperidine

phenyllithium

Refernces

• 1、 -. "Umerammonium bromide intermediate and preparation method thereof". . . Retrieved 2021/03/13.
• 2、 Gu, Jianhui,Zhang, Jie,Wang, Xuan,Wang, Guoping. "Convenient new synthesis of umeclidinium bromide". supporting information. p. 995 - 1000. Retrieved 2018/05/23.