Umeclidinium

Identification

Name

Umeclidinium

Accession Number

DB09076

Description

Umeclidinium is a long-acting muscarinic antagonist (LAMA) used as maintenance treatment for symptoms of chronic obstructive pulmonary disease (COPD). It is available as a once-daily inhalation monotherapy or as a fixed-dose combination product with the long-acting beta2-agonist vilanterol. 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%. By blocking the M3 muscarinic receptor which is highly expressed in airway smooth muscle of the lungs, umeclidinium inhibits the binding of acetylcholine and thereby opens up the airways by preventing bronchoconstriction. Its use has been shown to provide clinically significant, sustained improvements in lung function.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Umeclidinium (DB09076)

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Weight

Average: 428.595
Monoisotopic: 428.258405759

Chemical Formula

C₂₉H₃₄NO₂

Synonyms

• 1-[2-(benzyloxy)ethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane
• Umeclidinium

External IDs

• GSK-573719
• GSK573719
• GSK573719A

Pharmacology

Indication

Indicated for the long-term, once-daily, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD).

Associated Conditions

• Chronic Obstructive Pulmonary Disease (COPD)

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Umeclidinium is a long-acting, antimuscarinic agent, which is often referred to as an anticholinergic. It has similar affinity to the subtypes of muscarinic receptors M1 to M5. In the airways, it exhibits pharmacological effects through the inhibition of M3 receptor at the smooth muscle leading to bronchodilation.

Target	Actions	Organism
NMuscarinic acetylcholine receptor M1	antagonist	Humans
AMuscarinic acetylcholine receptor M2	antagonist	Humans
AMuscarinic acetylcholine receptor M3	antagonist	Humans
NMuscarinic acetylcholine receptor M4	antagonist	Humans
NMuscarinic acetylcholine receptor M5	antagonist	Humans

Absorption

Cmax occurred at 5 to 15 minutes, with steady state concentrations arriving in 14 days with 1.8-fold accumulation.

Volume of distribution

Mean volume of distribution was 86 L.

Protein binding

89%

Metabolism

In vitro data showed that umeclidinium is primarily metabolized by the enzyme cytochrome P450 2D6 (CYP2D6) and is a substrate for the P-glycoprotein (P-gp) transporter. The primary metabolic routes for umeclidinium are oxidative (hydroxylation, Odealkylation) followed by conjugation (e.g., glucuronidation), resulting in a range of metabolites with either reduced pharmacological activity or for which the pharmacological activity has not been established. Systemic exposure to the metabolites is low.

Route of elimination

Following intravenous dosing with radiolabeled umeclidinium, mass balance showed 58% of the radiolabel in the feces and 22% in the urine.

Half-life

The effective half-life after once daily dosing is 11 hours.

Clearance

Not Available

Adverse Effects

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Toxicity

In clinical trials, the most common adverse effects of umeclidinium were nasopharyngitis, upper respiratory tract infection, cough, and arthralgia. Atrial fibrillation occurred in <1% of patients, but was more common among patients treated with umeclidinium than in those treated with placebo. Anticholinergics like umeclidinium should be used with caution in patients with narrow-angle glaucoma and in those with prostatic hyperplasia or bladder-neck obstruction. Inhaled medications can cause paradoxical bronchospasm, which can be fatal.

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abatacept	The metabolism of Umeclidinium can be increased when combined with Abatacept.
Abiraterone	The metabolism of Umeclidinium can be decreased when combined with Abiraterone.
Acebutolol	The metabolism of Umeclidinium can be decreased when combined with Acebutolol.
Acetaminophen	The metabolism of Umeclidinium can be decreased when combined with Acetaminophen.
Acetazolamide	Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Umeclidinium.
Acetophenazine	Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Umeclidinium.
Aclidinium	The risk or severity of adverse effects can be increased when Umeclidinium is combined with Aclidinium.
Adalimumab	The metabolism of Umeclidinium can be increased when combined with Adalimumab.
Adenosine	The risk or severity of Tachycardia can be increased when Adenosine is combined with Umeclidinium.
Afatinib	The serum concentration of Umeclidinium can be increased when it is combined with Afatinib.

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Severity
Severity
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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Umeclidinium bromide	7AN603V4JV	869113-09-7	PEJHHXHHNGORMP-UHFFFAOYSA-M

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Anoro	Powder, metered		Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable
Anoro	Powder, metered		Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable
Anoro	Powder, metered		Respiratory (inhalation)	Glaxo Smith Kline (Ireland) Limited	2014-05-08	Not applicable
Incruse	Powder, metered	55 μg	Respiratory (inhalation)	Glaxo Group Limited	2014-04-28	Not applicable
Incruse	Powder, metered	55 μg	Respiratory (inhalation)	Glaxo Group Limited	2014-04-28	Not applicable
Incruse	Powder, metered	55 μg	Respiratory (inhalation)	Glaxo Group Limited	2014-04-28	Not applicable
Incruse Ellipta	Powder	62.5 mcg	Respiratory (inhalation)	Glaxosmithkline Inc	2015-04-27	Not applicable
Incruse Ellipta	Aerosol, powder	62.5 ug/1	Oral	GlaxoSmithKline LLC	2014-04-30	Not applicable

Additional Data Available

Application Number
Application Number
Available for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Anoro Ellipta	Umeclidinium bromide (62.5 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2014-01-31	Not applicable
Anoro Ellipta	Umeclidinium (62.5 mcg) + Vilanterol (25 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2014-03-14	Not applicable
Trelegy Ellipta	Umeclidinium bromide (62.5 ug/1) + Fluticasone furoate (100 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2017-09-18	Not applicable
Trelegy Ellipta	Umeclidinium bromide (62.5 ug/1) + Fluticasone furoate (200 ug/1) + Vilanterol trifenatate (25 ug/1)	Powder	Respiratory (inhalation)	GlaxoSmithKline LLC	2020-09-09	Not applicable
Trelegy Ellipta	Umeclidinium (62.5 mcg) + Fluticasone furoate (100 mcg) + Vilanterol (25 mcg)	Powder	Respiratory (inhalation)	Glaxosmithkline Inc	2018-05-30	Not applicable

Categories

ATC Codes

R03AL08 — Vilanterol, umeclidinium bromide and fluticasone furoate

• R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

R03AL03 — Vilanterol and umeclidinium bromide

• R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
• R03A — ADRENERGICS, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

R03BB07 — Umeclidinium bromide

• R03BB — Anticholinergics
• R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
• R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
• R — RESPIRATORY SYSTEM

Drug Categories

• Adrenergics, Inhalants
• Agents producing tachycardia
• Agents to Treat Airway Disease
• Anticholinergic Agents
• Antimuscarinics Antispasmodics
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 Substrates
• Drugs for Obstructive Airway Diseases
• Muscarinic Antagonists
• P-glycoprotein substrates
• Pulmonary Disease, Chronic Obstructive, drug therapy

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Benzylethers / Quinuclidines / Aralkylamines / Piperidines / Tetraalkylammonium salts / Tertiary alcohols / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Aromatic alcohols / Organic cations

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Substituents

Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzylether / Dialkyl ether / Diphenylmethane / Ether / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organic oxygen compound / Organic salt / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Piperidine / Quaternary ammonium salt / Quinuclidine / Tertiary alcohol / Tetraalkylammonium salt

show 14 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Chemical Identifiers

UNII

GE2T1418SV

CAS number

869185-19-3

InChI Key

FVTWTVQXNAJTQP-UHFFFAOYSA-N

InChI

InChI=1S/C29H34NO2/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/q+1

IUPAC Name

1-[2-(benzyloxy)ethyl]-4-(hydroxydiphenylmethyl)-1-azabicyclo[2.2.2]octan-1-ium

SMILES

OC(C1=CC=CC=C1)(C1=CC=CC=C1)C12CC[N+](CCOCC3=CC=CC=C3)(CC1)CC2

References

General References

1. Feldman GJ, Edin A: The combination of umeclidinium bromide and vilanterol in the management of chronic obstructive pulmonary disease: current evidence and future prospects. Ther Adv Respir Dis. 2013 Dec;7(6):311-9. doi: 10.1177/1753465813499789. Epub 2013 Sep 3. [PubMed:24004659]
2. Decramer M, Maltais F, Feldman G, Brooks J, Harris S, Mehta R, Crater G: Bronchodilation of umeclidinium, a new long-acting muscarinic antagonist, in COPD patients. Respir Physiol Neurobiol. 2013 Jan 15;185(2):393-9. doi: 10.1016/j.resp.2012.08.022. Epub 2012 Sep 28. [PubMed:23026438]
3. Tal-Singer R, Cahn A, Mehta R, Preece A, Crater G, Kelleher D, Pouliquen IJ: Initial assessment of single and repeat doses of inhaled umeclidinium in patients with chronic obstructive pulmonary disease: two randomised studies. Eur J Pharmacol. 2013 Feb 15;701(1-3):40-8. doi: 10.1016/j.ejphar.2012.12.019. Epub 2012 Dec 28. [PubMed:23276660]
4. Trivedi R, Richard N, Mehta R, Church A: Umeclidinium in patients with COPD: a randomised, placebo-controlled study. Eur Respir J. 2014 Jan;43(1):72-81. doi: 10.1183/09031936.00033213. Epub 2013 Aug 15. [PubMed:23949963]
5. Goyal N, Beerahee M, Kalberg C, Church A, Kilbride S, Mehta R: Population pharmacokinetics of inhaled umeclidinium and vilanterol in patients with chronic obstructive pulmonary disease. Clin Pharmacokinet. 2014 Jul;53(7):637-48. doi: 10.1007/s40262-014-0143-4. [PubMed:24756395]
6. Scott LJ, Hair P: Umeclidinium/Vilanterol: first global approval. Drugs. 2014 Mar;74(3):389-95. doi: 10.1007/s40265-014-0186-8. [PubMed:24532124]
7. Salmon M, Luttmann MA, Foley JJ, Buckley PT, Schmidt DB, Burman M, Webb EF, DeHaas CJ, Kotzer CJ, Barrett VJ, Slack RJ, Sarau HM, Palovich MR, Laine DI, Hay DW, Rumsey WL: Pharmacological characterization of GSK573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases. J Pharmacol Exp Ther. 2013 May;345(2):260-70. doi: 10.1124/jpet.112.202051. Epub 2013 Feb 22. [PubMed:23435542]

External Links

KEGG Drug

D10180

PubChem Compound

11519070

PubChem Substance

347827824

ChemSpider

9693858

BindingDB

50267614

RxNav

1487514

ChEBI

79041

ChEMBL

CHEMBL1187833

ZINC

ZINC000034608502

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Umeclidinium_bromide

AHFS Codes

• 12:08.08 — Antimuscarinics Antispasmodics

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Not Yet Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Heart Failure	1
4	Recruiting	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Withdrawn	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Completed	Other	Chronic Obstructive Pulmonary Disease (COPD)	1
3	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	23
3	Not Yet Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD) / Non-Small Cell Lung Carcinoma (NSCLC)	1
3	Withdrawn	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
2	Completed	Diagnostic	Asthma	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Powder, metered	Respiratory (inhalation)
Powder	Respiratory (inhalation)	55 µg
Aerosol, powder	Respiratory (inhalation)	55 mcg
Powder	Oral; Respiratory (inhalation)	55 mcg
Powder	Respiratory (inhalation)	92 MCG
Tablet	Oral	62.5 mg
Powder, metered	Respiratory (inhalation)	55 μg
Aerosol, powder	Oral	62.5 ug/1
Powder	Respiratory (inhalation)	62.5 mcg
Aerosol, powder	Respiratory (inhalation)	62.5 mg
Powder	Respiratory (inhalation)	55 mcg
Aerosol, powder	Respiratory (inhalation)	62.5 mcg
Powder	Respiratory (inhalation)
Aerosol, powder	Respiratory (inhalation)	100 mcg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
Unlock Additional Data
US5873360	Yes	1999-02-23	2016-08-23
US7101866	No	2006-09-05	2021-08-03
US7439393	No	2008-10-21	2022-09-11
US6759398	No	2004-07-06	2021-08-03
USRE44874	No	2014-04-29	2023-03-23
US6537983	No	2003-03-25	2021-08-03
US8511304	No	2013-08-20	2027-06-14
US7629335	No	2009-12-08	2021-08-03
US8161968	No	2012-04-24	2028-02-05
US8746242	No	2014-06-10	2030-10-11
US8113199	No	2012-02-14	2027-10-23
US7776895	No	2010-08-17	2022-09-11
US8534281	No	2013-09-17	2029-08-10
US6878698	No	2005-04-12	2021-08-03
US8309572	No	2012-11-13	2025-04-27
US8183257	No	2012-05-22	2025-07-27
US7488827	No	2009-02-10	2025-04-27
US7498440	No	2009-03-03	2025-04-27
US8201556	No	2012-06-19	2029-02-05
US9333310	No	2016-05-10	2027-10-02
US9750726	No	2017-09-05	2030-11-29
US9750762	No	2017-09-05	2030-11-29

Additional Data Available

Filed On
Filed On
Available for Purchase
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.94e-05 mg/mL	ALOGPS
logP	2.88	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	50.42 Å3	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available

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Drug created on May 19, 2015 10:00 / Updated on October 29, 2020 19:25