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

Details

Stereochemistry ACHIRAL
Molecular Formula C29H34NO2
Molecular Weight 428.5858
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of UMECLIDINIUM

SMILES

OC(C1=CC=CC=C1)(C2=CC=CC=C2)C34CC[N+](CCOCC5=CC=CC=C5)(CC3)CC4

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 427.5778
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.06 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ANORO ELLIPTA

Cmax

ValueDoseCo-administeredAnalytePopulation
245 pg/mL
62.5 μg 1 times / day multiple, oral
UMECLIDINIUM plasma
Homo sapiens
258 pg/mL
62.5 μg 1 times / day multiple, oral
UMECLIDINIUM plasma
Homo sapiens
995.9 pg/mL
500 μg single, oral
UMECLIDINIUM plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
304 pg × h/mL
62.5 μg 1 times / day multiple, oral
UMECLIDINIUM plasma
Homo sapiens
298 pg × h/mL
62.5 μg 1 times / day multiple, oral
UMECLIDINIUM plasma
Homo sapiens
575.7 pg × h/mL
500 μg single, oral
UMECLIDINIUM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
500 μg single, oral
UMECLIDINIUM plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
GE2T1418SV
Record Status Validated (UNII)
Record Version