| Identification | Back Directory | [Name]
Umeclidinium bromide | [CAS]
869113-09-7 | [Synonyms]
CS-1562
UMeclidiuM
GSK573719A
Umeclidiniu
umeclidinium
UMeclidiniuM broMide
Umeclinidium bromide
Jmechlidinium bromide
Umeclidinium(GSK573719A)
UMeclidiniuM BroMide (API)
Umeclidinium bromide, >=98%
1-Azoniabicyclo[2.2.2]octane
Umeclidinium bromide(GSK573719A)
GSK573719A;GSK-573719A;GSK 573719A
High purity CAS 869113-09-7 Umeclidinium bromide in stock
1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide
1-[2-(Benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-quinuclidinium Bromide
diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol
DIPHENYL-[1-(2-PHENYLMETHOXYETHYL)-1-AZONIABICYCLO[2.2.2]OCTAN-4-YL]METHANOL;BROMIDE
Umeclidinium bromide 1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide
Umeclidinium bromide 1-(2-(benzyloxy)ethyl)-4-(hydroxydiphenylmethyl)quinuclidin-1-ium bromide
4-[Hydroxy(diphenyl)methyl]-1-[2-[(phenylmethyl)oxy]ethyl]-1-azoniabicyclo[2.2.2]octane bromide
1-Azoniabicyclo[2.2.2]octane, 4-(hydroxydiphenylMethyl)-1-[2-(phenylMethoxy)ethyl]-, broMide (1:1) | [EINECS(EC#)]
638-761-1 | [Molecular Formula]
C29H34BrNO2 | [MDL Number]
MFCD27976798 | [MOL File]
869113-09-7.mol | [Molecular Weight]
508.49 |
| Chemical Properties | Back Directory | [Melting point ]
>231°C (dec.) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: A quaternary ammonium salt that is the bromide salt of umeclidinium. Used in combination with vilanterol for long-term maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease. | [Synthesis]
Commercially available ethyl isonipecotate (278) was alkylated
with 1-bromo-2-chloroethane in the presence of K2CO3 in acetone
to give ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (279). This
material was then treated with lithium diisopropylamine (LDA) in
THF to affect a transannular substitution reaction resulting in the
cyclized quinuclidine 280 in 96% yield. Excess of phenyllithium
was added to ester 280 in THF starting at low temperature then
gradually warming to room temperature to give tertiary alcohol 281 in 61% yield. Amine 281 was finally alkylated with benzyl 2-
bromoethyl ether (282) in MeCN/CHCl3 at elevated temperatures
to afford umeclidinium bromide (XXXV) in 69% yield.
| [References]
[1] salmon m, luttmann m a, foley j j, et al. pharmacological characterization of gsk573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases. journal of pharmacology and experimental therapeutics, 2013, 345(2): 260-270. |
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