U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C29H34NO2.Br
Molecular Weight 508.4904
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMECLIDINIUM BROMIDE

SMILES

c1ccc(cc1)COCC[N+]23CCC(CC2)(CC3)C(c4ccccc4)(c5ccccc5)O.[Br-]

InChI

InChIKey=PEJHHXHHNGORMP-UHFFFAOYSA-M
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

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C29H33NO2
Molecular Weight 427.5789
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=19317446; http://www.ncbi.nlm.nih.gov/pubmed/?term=23435542; http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002751/WC500168425.pdf

Umeclidinium (used as a bromide salt) is a long-acting, antimuscarinic antagonist, often referred to as an anticholinergic, developed for the treatment of chronic obstructive pulmonary disease (COPD) (alone and in combination with Vilanterol - long-acting beta2-adrenergic agonist). Umeclidinium has similar affinity to the subtypes of muscarinic receptors M1 to M5 with Ki values of 0.16 nM, 0.15 nM, 0.06 nM, 0.05 nM and 0.13 nM for M1, M2, M3, M4 and M5, respectively. Umeclidinium is selective against mAChR over other unrelated receptors or channels such as κ and σ opiod receptors, Na+ channel and dopamine transporter. In the airways, it exhibits pharmacological effects through the inhibition of M3 receptor at the smooth muscle leading to bronchodilation. There is potential for an additive interaction with concomitantly used anticholinergic medicines.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P20309
Gene ID: 1131.0
Gene Symbol: CHRM3
Target Organism: Homo sapiens (Human)
0.06 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ANORO ELLIPTA

Approved Use

Indicated for the long-term, once-daily, maintenance treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema. Is NOT indicated for the relief of acute bronchospasm or for the treatment of asthma.

Launch Date

1.38732477E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
245 pg/mL
62.5 μg 1 times / day multiple, oral
dose: 62.5 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: VILANTEROL
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
258 pg/mL
62.5 μg 1 times / day multiple, oral
dose: 62.5 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
995.9 pg/mL
500 μg single, oral
dose: 500 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
304 pg × h/mL
62.5 μg 1 times / day multiple, oral
dose: 62.5 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered: VILANTEROL
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
298 pg × h/mL
62.5 μg 1 times / day multiple, oral
dose: 62.5 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
575.7 pg × h/mL
500 μg single, oral
dose: 500 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
500 μg single, oral
dose: 500 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
UMECLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
Other AEs: Cough, Headache...
Other AEs:
Cough (14%)
Headache (10%)
Nasopharyngitis (7%)
Upper respiratory tract infection (3%)
Oropharyngeal pain (3%)
Sources:
250 ug 1 times / day steady, respiratory
Highest studied dose
Dose: 250 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 250 ug, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Asthma
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache 10%
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
Cough 14%
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
Oropharyngeal pain 3%
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
Upper respiratory tract infection 3%
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
Nasopharyngitis 7%
125 ug 1 times / day steady, respiratory
Dose: 125 ug, 1 times / day
Route: respiratory
Route: steady
Dose: 125 ug, 1 times / day
Sources:
unhealthy, 64.6 years
n = 69
Health Status: unhealthy
Condition: COPD
Age Group: 64.6 years
Sex: M+F
Population Size: 69
Sources:
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
weak (co-administration study)
Comment: coadministered with verapamil, a potent inhibitor of P-gp and moderate inhibitor of CYP3A4. There was no effect of verapamil on Cmax, and a moderate increase (1.4-fold) in AUC for UMEC
Page: 57.0
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
weak (co-administration study)
Comment: coadministered with verapamil, a potent inhibitor of P-gp and moderate inhibitor of CYP3A4. There was no effect of verapamil on Cmax, and a moderate increase (1.4-fold) in AUC for UMEC
Page: 7,31
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Discovery of novel 1-azoniabicyclo[2.2.2]octane muscarinic acetylcholine receptor antagonists.
2009 Apr 23
The combination of umeclidinium bromide and vilanterol in the management of chronic obstructive pulmonary disease: current evidence and future prospects.
2013 Dec
Pharmacological characterization of GSK573719 (umeclidinium): a novel, long-acting, inhaled antagonist of the muscarinic cholinergic receptors for treatment of pulmonary diseases.
2013 May
Patents

Sample Use Guides

ANORO ELLIPTA (umeclidinium/vilanterol 62.5 mcg/25 mcg) should be administered as 1 inhalation once daily by the orally inhaled route only. ANORO ELLIPTA should be taken at the same time every day. Do not use ANORO ELLIPTA more than 1 time every 24 hours. No dosage adjustment is required for geriatric patients, patients with renal impairment, or patients with moderate hepatic impairment.
Route of Administration: Respiratory
Using isolated human bronchial strips, umeclidinium was tested at concentrations from 1 nM to 100 nM ans showed potent inhibition of cells contraction. For these means segments of human bronchus were incubated with umeclidinium for 120 minutes prior to cumulative addition of carbachol in conventional tissue baths heated at 37°C.
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:00:41 UTC 2021
Edited
by admin
on Sat Jun 26 06:00:41 UTC 2021
Record UNII
7AN603V4JV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UMECLIDINIUM BROMIDE
INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
UMECLIDINIUM BROMIDE COMPONENT OF TRELEGY ELLIPTA
Brand Name English
TRELEGY ELLIPTA COMPONENT UMECLIDINIUM BROMIDE
Brand Name English
UMECLIDINIUM BROMIDE [VANDF]
Common Name English
UMECLIDINIUM BROMIDE [ORANGE BOOK]
Common Name English
UMECLIDINIUM BROMIDE [WHO-DD]
Common Name English
GSK573719A
Code English
UMECLIDINIUM BROMIDE [USAN]
Common Name English
UMECLIDINIUM BROMIDE [INN]
Common Name English
1-(2-((BENZYL)OXY)ETHYL)4-(HYDROXYDI(PHENYL)METHYL)-1-AZABICYCLO(2.2.2)OCTAN-1-IUM BROMIDE
Systematic Name English
UMEC
Common Name English
INCRUSE ELLIPTA
Brand Name English
ANORO ELLIPTA
Brand Name English
GSK-573719A
Code English
UMECLIDINIUM BROMIDE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC R03AL03
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
WHO-ATC R03AL08
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
EMA ASSESSMENT REPORTS LAVENTAIR (AUTHORIZED: PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
EMA ASSESSMENT REPORTS ANORO (AUTHORIZED: PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
WHO-ATC R03BB07
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
EMA ASSESSMENT REPORTS INCRUSE (AUTHORIZED: PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
WHO-VATC QR03AL03
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
Code System Code Type Description
RXCUI
1487512
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB09076
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
NCI_THESAURUS
C152797
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
PUBCHEM
11519069
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
EVMPD
SUB119778
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
MERCK INDEX
M11712
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1187833
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
JAPANESE REVIEW
ANORO ELLIPTA
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY APPROVED JULY 2014
EPA CompTox
869113-09-7
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
CAS
869113-09-7
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
FDA UNII
7AN603V4JV
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
INN
9551
Created by admin on Sat Jun 26 06:00:41 UTC 2021 , Edited by admin on Sat Jun 26 06:00:41 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY