Identification

Name
Umeclidinium
Accession Number
DB09076
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • 1-[2-(benzyloxy)ethyl]-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane
External IDs
GSK-573719 / GSK573719 / GSK573719A
Product Ingredients
IngredientUNIICASInChI Key
Umeclidinium bromide7AN603V4JV869113-09-7PEJHHXHHNGORMP-UHFFFAOYSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IncrusePowder, metered55 μgRespiratory (inhalation)Glaxo Group Limited2014-04-28Not applicableEu
IncrusePowder, metered55 μgRespiratory (inhalation)Glaxo Group Limited2014-04-28Not applicableEu
IncrusePowder, metered55 μgRespiratory (inhalation)Glaxo Group Limited2014-04-28Not applicableEu
Incruse ElliptaPowder62.5 mcgRespiratory (inhalation)Glaxosmithkline Inc2015-04-27Not applicableCanada
Incruse ElliptaAerosol, powder62.5 ug/1OralGlaxosmithkline Inc2014-04-30Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AnoroUmeclidinium bromide (55 micrograms) + Vilanterol Trifenatate (22 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
AnoroUmeclidinium bromide (55 micrograms) + Vilanterol Trifenatate (22 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
AnoroUmeclidinium bromide (55 micrograms) + Vilanterol Trifenatate (22 micrograms)Powder, meteredRespiratory (inhalation)Glaxo Group Limited2014-05-08Not applicableEu
Anoro ElliptaUmeclidinium (62.5 mcg) + Vilanterol (25 mcg)PowderRespiratory (inhalation)Glaxosmithkline Inc2014-03-14Not applicableCanada
Anoro ElliptaUmeclidinium bromide (62.5 ug/1) + Vilanterol Trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2014-01-31Not applicableUs
Trelegy ElliptaUmeclidinium bromide (62.5 ug/1) + Fluticasone furoate (100 ug/1) + Vilanterol Trifenatate (25 ug/1)PowderRespiratory (inhalation)Glaxosmithkline Inc2017-09-18Not applicableUs
Categories
UNII
GE2T1418SV
CAS number
869185-19-3
Weight
Average: 428.595
Monoisotopic: 428.258405759
Chemical Formula
C29H34NO2
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

Pharmacology

Indication

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

Structured Indications
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.

TargetActionsOrganism
NMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
AMuscarinic acetylcholine receptor M3
antagonist
Human
NMuscarinic acetylcholine receptor M4
antagonist
Human
NMuscarinic acetylcholine receptor M5
antagonist
Human
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
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
DrugInteractionDrug group
1,10-PhenanthrolineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with 1,10-Phenanthroline.Experimental
AbirateroneThe serum concentration of Umeclidinium can be increased when it is combined with Abiraterone.Approved
AclidiniumAclidinium may increase the anticholinergic activities of Umeclidinium.Approved
AlcuroniumAlcuronium may increase the anticholinergic activities of Umeclidinium.Experimental
AlfentanilThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Alfentanil.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Alphacetylmethadol.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Alphaprodine.Illicit
AmbenoniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Ambenonium.Approved
AmiodaroneThe metabolism of Umeclidinium can be decreased when combined with Amiodarone.Approved, Investigational
AmoxapineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Amoxapine.Approved
Anisotropine MethylbromideAnisotropine Methylbromide may increase the anticholinergic activities of Umeclidinium.Approved
ApalutamideThe serum concentration of Umeclidinium can be decreased when it is combined with Apalutamide.Approved, Investigational
ArtemetherThe metabolism of Umeclidinium can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Umeclidinium can be decreased when combined with Atomoxetine.Approved
AtracuriumAtracurium may increase the anticholinergic activities of Umeclidinium.Approved, Experimental, Investigational
Atracurium besylateAtracurium besylate may increase the anticholinergic activities of Umeclidinium.Approved
AtropineAtropine may increase the anticholinergic activities of Umeclidinium.Approved, Vet Approved
BenactyzineBenactyzine may increase the anticholinergic activities of Umeclidinium.Withdrawn
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Umeclidinium.Approved
BenzatropineBenzatropine may increase the anticholinergic activities of Umeclidinium.Approved
BetaxololThe metabolism of Umeclidinium can be decreased when combined with Betaxolol.Approved, Investigational
BezitramideThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Bezitramide.Experimental, Illicit, Withdrawn
BiperidenBiperiden may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
BornaprineBornaprine may increase the anticholinergic activities of Umeclidinium.Experimental
Botulinum Toxin Type AUmeclidinium may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BUmeclidinium may increase the anticholinergic activities of Botulinum Toxin Type B.Approved, Investigational
BuprenorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BupropionThe metabolism of Umeclidinium can be decreased when combined with Bupropion.Approved
ButorphanolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Butorphanol.Approved, Illicit, Vet Approved
ButylscopolamineButylscopolamine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Carfentanil.Illicit, Investigational, Vet Approved
CelecoxibThe metabolism of Umeclidinium can be decreased when combined with Celecoxib.Approved, Investigational
ChloroquineThe metabolism of Umeclidinium can be decreased when combined with Chloroquine.Approved, Investigational, Vet Approved
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Umeclidinium.Approved, Vet Approved
ChlorphenoxamineChlorphenoxamine may increase the anticholinergic activities of Umeclidinium.Withdrawn
ChlorpromazineThe metabolism of Umeclidinium can be decreased when combined with Chlorpromazine.Approved, Investigational, Vet Approved
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Umeclidinium.Approved
CholecalciferolThe metabolism of Umeclidinium can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Umeclidinium can be decreased when combined with Cimetidine.Approved, Investigational
CimetropiumUmeclidinium may increase the anticholinergic activities of Cimetropium.Experimental, Investigational
CinacalcetThe metabolism of Umeclidinium can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Umeclidinium can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Umeclidinium can be decreased when combined with Clemastine.Approved, Investigational
ClobazamThe metabolism of Umeclidinium can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Umeclidinium can be decreased when combined with Clomipramine.Approved, Investigational, Vet Approved
ClotrimazoleThe metabolism of Umeclidinium can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Umeclidinium can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Umeclidinium can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Umeclidinium can be decreased when combined with Cocaine.Approved, Illicit
CodeineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Coumaphos.Vet Approved
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Umeclidinium.Experimental
CyclopentolateCyclopentolate may increase the anticholinergic activities of Umeclidinium.Approved
DarifenacinDarifenacin may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
DarunavirThe serum concentration of Umeclidinium can be increased when it is combined with Darunavir.Approved
DecamethoniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Decamethonium.Approved
DelavirdineThe metabolism of Umeclidinium can be decreased when combined with Delavirdine.Approved
DemecariumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Demecarium.Approved
DesipramineThe metabolism of Umeclidinium can be decreased when combined with Desipramine.Approved, Investigational
DesloratadineDesloratadine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
DexetimideDexetimide may increase the anticholinergic activities of Umeclidinium.Withdrawn
DextromoramideThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dextropropoxyphene.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dezocine.Approved, Investigational
DichlorvosThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineDicyclomine may increase the anticholinergic activities of Umeclidinium.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Dihydromorphine.Experimental, Illicit
DiphenhydramineThe metabolism of Umeclidinium can be decreased when combined with Diphenhydramine.Approved, Investigational
DiphenoxylateThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Diphenoxylate.Approved, Illicit
DistigmineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Distigmine.Experimental
DonepezilThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Donepezil.Approved
DosulepinThe metabolism of Umeclidinium can be decreased when combined with Dosulepin.Approved
DPDPEThe risk or severity of adverse effects can be increased when Umeclidinium is combined with DPDPE.Experimental
DronabinolUmeclidinium may increase the tachycardic activities of Dronabinol.Approved, Illicit
DronedaroneThe metabolism of Umeclidinium can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Umeclidinium can be decreased when combined with Duloxetine.Approved
EchothiophateThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Edrophonium.Approved
EliglustatThe metabolism of Umeclidinium can be decreased when combined with Eliglustat.Approved
EluxadolineUmeclidinium may increase the constipating activities of Eluxadoline.Approved, Investigational
EmeproniumEmepronium may increase the anticholinergic activities of Umeclidinium.Experimental
EpitizideThe serum concentration of Epitizide can be increased when it is combined with Umeclidinium.Experimental
EtanautineEtanautine may increase the anticholinergic activities of Umeclidinium.Experimental
EthopropazineEthopropazine may increase the anticholinergic activities of Umeclidinium.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Etorphine.Illicit, Vet Approved
EtybenzatropineEtybenzatropine may increase the anticholinergic activities of Umeclidinium.Experimental
FentanylThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineFesoterodine may increase the anticholinergic activities of Umeclidinium.Approved
FluoxetineThe metabolism of Umeclidinium can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Umeclidinium can be decreased when combined with Fluvoxamine.Approved, Investigational
GalantamineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Galantamine.Approved
GallamineGallamine may increase the anticholinergic activities of Umeclidinium.Experimental
Gallamine TriethiodideGallamine Triethiodide may increase the anticholinergic activities of Umeclidinium.Approved
Glucagon recombinantThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Glucagon recombinant.Approved
GlycopyrroniumGlycopyrronium may increase the anticholinergic activities of Umeclidinium.Approved, Investigational, Vet Approved
HaloperidolThe metabolism of Umeclidinium can be decreased when combined with Haloperidol.Approved
HeroinThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Heroin.Approved, Illicit, Investigational
HexamethoniumHexamethonium may increase the anticholinergic activities of Umeclidinium.Experimental
HomatropineHomatropine may increase the anticholinergic activities of Umeclidinium.Approved
Human secretinThe therapeutic efficacy of Human secretin can be decreased when used in combination with Umeclidinium.Approved
Huperzine AThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Huperzine A.Approved, Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Umeclidinium.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Umeclidinium.Approved, Investigational
HydromorphoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Hydromorphone.Approved, Illicit
HyoscyamineHyoscyamine may increase the anticholinergic activities of Umeclidinium.Approved
ImipramineThe metabolism of Umeclidinium can be decreased when combined with Imipramine.Approved
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Umeclidinium.Approved
IndinavirThe metabolism of Umeclidinium can be decreased when combined with Indinavir.Approved
IpidacrineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Ipidacrine.Experimental
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Umeclidinium.Approved
IsavuconazoleThe serum concentration of Umeclidinium can be increased when it is combined with Isavuconazole.Approved, Investigational
IsoflurophateThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Isoflurophate.Approved, Investigational, Withdrawn
IsoniazidThe metabolism of Umeclidinium can be decreased when combined with Isoniazid.Approved, Investigational
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Umeclidinium.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Ketobemidone.Approved, Investigational
KetoconazoleThe metabolism of Umeclidinium can be decreased when combined with Ketoconazole.Approved, Investigational
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Levomethadyl Acetate.Approved, Investigational
LevorphanolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Levorphanol.Approved
LofentanilThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Lofentanil.Illicit
LopinavirThe metabolism of Umeclidinium can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Umeclidinium can be decreased when combined with Lorcaserin.Approved
LumacaftorThe serum concentration of Umeclidinium can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Umeclidinium can be decreased when combined with Lumefantrine.Approved
MalathionThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Malathion.Approved, Investigational
ManidipineThe metabolism of Umeclidinium can be decreased when combined with Manidipine.Approved, Investigational
MazaticolMazaticol may increase the anticholinergic activities of Umeclidinium.Experimental
MecamylamineMecamylamine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
MefloquineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Mefloquine.Approved, Investigational
MemantineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Memantine.Approved, Investigational
MeptazinolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Meptazinol.Experimental
MethadoneThe metabolism of Umeclidinium can be decreased when combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Methadyl Acetate.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineMethantheline may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
MethotrimeprazineThe metabolism of Umeclidinium can be decreased when combined with Methotrimeprazine.Approved, Investigational
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Umeclidinium.Approved
Methylscopolamine bromideMethylscopolamine bromide may increase the anticholinergic activities of Umeclidinium.Approved
MetixeneMetixene may increase the anticholinergic activities of Umeclidinium.Approved
MetoclopramideThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Metoclopramide.Approved, Investigational
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Umeclidinium.Approved
MetoprololThe metabolism of Umeclidinium can be decreased when combined with Metoprolol.Approved, Investigational
MianserinMianserin may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
MidostaurinThe metabolism of Umeclidinium can be decreased when combined with Midostaurin.Approved, Investigational
MinaprineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Minaprine.Approved
MirabegronThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Mirabegron.Approved
MorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Morphine.Approved, Investigational
NabiloneUmeclidinium may increase the tachycardic activities of Nabilone.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Nalbuphine.Approved
NeostigmineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NevirapineThe metabolism of Umeclidinium can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of Umeclidinium can be decreased when combined with Nicardipine.Approved, Investigational
NicomorphineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Nicomorphine.Experimental
NilotinibThe metabolism of Umeclidinium can be decreased when combined with Nilotinib.Approved, Investigational
NormethadoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Normethadone.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Opium.Approved, Illicit
OrphenadrineOrphenadrine may increase the anticholinergic activities of Umeclidinium.Approved
OtiloniumOtilonium may increase the anticholinergic activities of Umeclidinium.Experimental, Investigational
OxitropiumOxitropium may increase the anticholinergic activities of Umeclidinium.Investigational
OxybutyninOxybutynin may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumOxyphenonium may increase the anticholinergic activities of Umeclidinium.Approved
PancuroniumPancuronium may increase the anticholinergic activities of Umeclidinium.Approved
PanobinostatThe serum concentration of Umeclidinium can be increased when it is combined with Panobinostat.Approved, Investigational
ParaoxonThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Paraoxon.Experimental
ParoxetineThe metabolism of Umeclidinium can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Umeclidinium can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentazocineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Pentazocine.Approved, Vet Approved
PentoliniumPentolinium may increase the anticholinergic activities of Umeclidinium.Approved
PethidineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Phenazocine.Experimental
PhenglutarimidePhenglutarimide may increase the anticholinergic activities of Umeclidinium.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Phenoperidine.Experimental
PhysostigmineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Physostigmine.Approved, Investigational
PipecuroniumPipecuronium may increase the anticholinergic activities of Umeclidinium.Approved
PirenzepinePirenzepine may increase the anticholinergic activities of Umeclidinium.Approved
PiritramideThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Piritramide.Approved, Investigational
PitolisantThe serum concentration of Umeclidinium can be decreased when it is combined with Pitolisant.Approved, Investigational
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Umeclidinium.Approved
Potassium ChlorideUmeclidinium may increase the ulcerogenic activities of Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
ProcyclidineProcyclidine may increase the anticholinergic activities of Umeclidinium.Approved
PromazineThe metabolism of Umeclidinium can be decreased when combined with Promazine.Approved, Vet Approved
PropanthelinePropantheline may increase the anticholinergic activities of Umeclidinium.Approved
PropiverinePropiverine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
PyridostigmineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Pyridostigmine.Approved, Investigational
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Umeclidinium.Approved
QuinidineQuinidine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
QuinineThe metabolism of Umeclidinium can be decreased when combined with Quinine.Approved
RamosetronUmeclidinium may increase the constipating activities of Ramosetron.Approved, Investigational
RanolazineThe serum concentration of Umeclidinium can be increased when it is combined with Ranolazine.Approved, Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Remifentanil.Approved
RitonavirThe metabolism of Umeclidinium can be decreased when combined with Ritonavir.Approved, Investigational
RivastigmineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Rivastigmine.Approved, Investigational
RolapitantThe metabolism of Umeclidinium can be decreased when combined with Rolapitant.Approved, Investigational
RopiniroleThe metabolism of Umeclidinium can be decreased when combined with Ropinirole.Approved, Investigational
RucaparibThe metabolism of Umeclidinium can be decreased when combined with Rucaparib.Approved, Investigational
ScopolamineScopolamine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Umeclidinium.Approved, Investigational
SertralineThe metabolism of Umeclidinium can be decreased when combined with Sertraline.Approved
SolifenacinSolifenacin may increase the anticholinergic activities of Umeclidinium.Approved
StiripentolThe metabolism of Umeclidinium can be decreased when combined with Stiripentol.Approved
SufentanilThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Sufentanil.Approved, Investigational
SulpirideUmeclidinium may increase the anticholinergic activities of Sulpiride.Approved, Investigational
TacrineThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Tacrine.Investigational, Withdrawn
TapentadolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Tapentadol.Approved
TerbinafineThe metabolism of Umeclidinium can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe metabolism of Umeclidinium can be decreased when combined with Thioridazine.Approved, Withdrawn
TiclopidineThe metabolism of Umeclidinium can be decreased when combined with Ticlopidine.Approved
TilidineThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Tilidine.Experimental
TiotropiumTiotropium may increase the anticholinergic activities of Umeclidinium.Approved
TipranavirThe metabolism of Umeclidinium can be decreased when combined with Tipranavir.Approved, Investigational
TolterodineTolterodine may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Umeclidinium is combined with Tramadol.Approved, Investigational
TranylcypromineThe metabolism of Umeclidinium can be decreased when combined with Tranylcypromine.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Umeclidinium.Approved, Vet Approved
TrihexyphenidylTrihexyphenidyl may increase the anticholinergic activities of Umeclidinium.Approved
TrimethaphanTrimethaphan may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
TropatepineTropatepine may increase the anticholinergic activities of Umeclidinium.Experimental
TropicamideTropicamide may increase the anticholinergic activities of Umeclidinium.Approved, Investigational
TrospiumTrospium may increase the anticholinergic activities of Umeclidinium.Approved
TubocurarineTubocurarine may increase the anticholinergic activities of Umeclidinium.Approved
VecuroniumVecuronium may increase the anticholinergic activities of Umeclidinium.Approved
VemurafenibThe serum concentration of Umeclidinium can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Umeclidinium can be decreased when combined with Venlafaxine.Approved
ZiprasidoneThe metabolism of Umeclidinium can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

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
ChEBI
79041
ChEMBL
CHEMBL1187833
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Umeclidinium_bromide
ATC Codes
R03BB07 — Umeclidinium bromideR03AL03 — Vilanterol and umeclidinium bromide
AHFS Codes
  • 12:08.08 — Antimuscarinics Antispasmodics

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherPulmonary Disease, Chronic Obstructive2
1CompletedPreventionHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentPulmonary Disease, Chronic Obstructive3
1, 2RecruitingTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
2CompletedDiagnosticAsthma Bronchial1
2CompletedTreatmentHyperhidrosis2
2CompletedTreatmentPulmonary Disease, Chronic Obstructive6
2RecruitingDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
2WithdrawnTreatmentAsthma Bronchial1
3Active Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
3CompletedOtherPulmonary Disease, Chronic Obstructive1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)3
3CompletedTreatmentPulmonary Disease, Chronic Obstructive14
3WithdrawnTreatmentPulmonary Disease, Chronic Obstructive1
4CompletedTreatmentPulmonary Disease, Chronic Obstructive1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Powder, meteredRespiratory (inhalation)
PowderRespiratory (inhalation)
Powder, meteredRespiratory (inhalation)55 μg
Aerosol, powderOral62.5 ug/1
PowderRespiratory (inhalation)62.5 mcg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5873360Yes1996-08-232016-08-23Us
US7101866No2001-08-032021-08-03Us
US7439393No2002-09-112022-09-11Us
US6759398No2001-08-032021-08-03Us
USRE44874No2003-03-232023-03-23Us
US6537983No2001-08-032021-08-03Us
US8511304No2007-06-142027-06-14Us
US7629335No2001-08-032021-08-03Us
US8161968No2008-02-052028-02-05Us
US8746242No2010-10-112030-10-11Us
US8113199No2007-10-232027-10-23Us
US7776895No2002-09-112022-09-11Us
US8534281No2009-08-102029-08-10Us
US6878698No2001-08-032021-08-03Us
US8309572No2005-04-272025-04-27Us
US8183257No2005-07-272025-07-27Us
US7488827No2005-04-272025-04-27Us
US7498440No2005-04-272025-04-27Us
US8201556No2009-02-052029-02-05Us
US9333310No2007-10-022027-10-02Us
US9750726No2010-11-292030-11-29Us
US9750762No2010-11-292030-11-29Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.94e-05 mg/mLALOGPS
logP2.88ALOGPS
logP0.68ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity141.75 m3·mol-1ChemAxon
Polarizability50.42 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

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
show 3 more
Substituents
Diphenylmethane / Benzylether / Quinuclidine / Aralkylamine / Piperidine / Tetraalkylammonium salt / Quaternary ammonium salt / Tertiary alcohol / Dialkyl ether / Ether
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. 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]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. 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]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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]

Drug created on May 19, 2015 10:00 / Updated on April 22, 2018 23:40