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Details

Stereochemistry ACHIRAL
Molecular Formula C29H34NO2
Molecular Weight 428.5868
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of UMECLIDINIUM

SMILES

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

InChI

InChIKey=FVTWTVQXNAJTQP-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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
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 13:09:37 UTC 2021
Edited
by admin
on Sat Jun 26 13:09:37 UTC 2021
Record UNII
GE2T1418SV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UMECLIDINIUM
DASH   USAN   VANDF   WHO-DD  
USAN  
Official Name English
1-(2-(BENZYLOXY)ETHYL)-4-(HYDROXY(DIPHENYL)METHYL)-1-AZONIABICYCLO(2.2.2)OCTANE
Systematic Name English
UMECLIDINIUM [VANDF]
Common Name English
UMECLIDINIUM CATION
Common Name English
GSK-573719
Code English
UMECLIDINIUM [WHO-DD]
Common Name English
UMECLIDINIUM ION
Common Name English
GSK573719
Code English
UMECLIDINIUM [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175574
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
WHO-ATC R03AL03
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
Code System Code Type Description
IUPHAR
7354
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
RXCUI
1487514
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY RxNorm
PUBCHEM
11519070
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
DRUG BANK
DB09076
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
DRUG CENTRAL
4816
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
NCI_THESAURUS
C152796
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
CAS
869185-19-3
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
EVMPD
SUB119777
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
FDA UNII
GE2T1418SV
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
LACTMED
Umeclidinium
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
EPA CompTox
869185-19-3
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL1187833
Created by admin on Sat Jun 26 13:09:38 UTC 2021 , Edited by admin on Sat Jun 26 13:09:38 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
However, because of low oral bioavailability, inhibition of P-gp is unlikely to have an impact on the overall bioavailability of UMEC.
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC