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Details

Stereochemistry ACHIRAL
Molecular Formula C35H43N5O4
Molecular Weight 597.747
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REVEFENACIN

SMILES

CN(CCN1CCC(CC1)OC(=O)NC2=CC=CC=C2C3=CC=CC=C3)C(=O)C4=CC=C(CN5CCC(CC5)C(N)=O)C=C4

InChI

InChIKey=FYDWDCIFZSGNBU-UHFFFAOYSA-N
InChI=1S/C35H43N5O4/c1-38(34(42)29-13-11-26(12-14-29)25-40-19-15-28(16-20-40)33(36)41)23-24-39-21-17-30(18-22-39)44-35(43)37-32-10-6-5-9-31(32)27-7-3-2-4-8-27/h2-14,28,30H,15-25H2,1H3,(H2,36,41)(H,37,43)

HIDE SMILES / InChI

Description

Revefenacin (trade name Yupelri is a long-acting muscarinic antagonist developed by Mylan Ireland ltd for the treatment of chronic obstructive pulmonary disease (COPD). It has similar affinity to the subtypes of muscarinic receptors M1 to M5. In the airways, it exhibits pharmacological effects through inhibition of M3 receptor at the smooth muscle leading to bronchodilation. The competitive and reversible nature of antagonism was shown with human and animal origin receptors and isolated organ preparations. In preclinical in vitro as well as in vivo models, prevention of methacholine- and acetylcholine-induced bronchoconstrictive effects was dose-dependent and lasted longer than 24 hours.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Revefenacin
2006
Patents

Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose of YUPELRI (revefenacin) inhalation solution is one 175 mkg unit-dose vial administered once daily by nebulizer using a mouthpiece.
Route of Administration: Respiratory
In Vitro Use Guide
CHO-K1 cell membrane fractions expressing human recombinant M2 or M3 mAChRs were incubated with [3H]revefenacin (18.5 Ci/mmol), [3H]glycopyrrolate (70 Ci_mmol_1), for 1 hours at 37°C or [3H]tiotropium (70 Ci/mmol) for 4 hours at 37°C. Nonspecific binding was defined in the presence of 10 mkmol/L atropine.
Name Type Language
REVEFENACIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
1-(2-(4-((4-CARBAMOYLPIPERIDIN-1-YL)METHYL)-N-METHYLBENZAMIDO)ETHYL)PIPERIDIN-4-YL N-((1,1'-BIPHENYL)-2-YL)CARBAMATE
Systematic Name English
GSK-1160724
Code English
TD-4208
Code English
GSK1160724
Code English
CARBAMIC ACID, N-(1,1'-BIPHENYL)-2-YL-, 1-(2-((4-((4-(AMINOCARBONYL)-1-PIPERIDINYL)METHYL)BENZOYL)METHYLAMINO)ETHYL)-4-PIPERIDINYL ESTER
Systematic Name English
REVEFENACIN [USAN]
Common Name English
REVEFENACIN [WHO-DD]
Common Name English
REVEFENACIN [INN]
Common Name English
BIPHENYL-2-YLCARBAMIC ACID, 1-(2-((4-(4-CARBAMOYLPIPERIDIN-1-YLMETHYL)BENZOYL)METHYLAMINO)ETHYL)PIPERIDIN-4-YL ESTER
Brand Name English
Code System Code Type Description
CAS
864750-70-9
Created by admin on Tue Mar 06 15:00:12 UTC 2018 , Edited by admin on Tue Mar 06 15:00:12 UTC 2018
PRIMARY
CAS
1211931-83-7
Created by admin on Tue Mar 06 15:00:12 UTC 2018 , Edited by admin on Tue Mar 06 15:00:12 UTC 2018
NO STRUCTURE GIVEN
INN
10112
Created by admin on Tue Mar 06 15:00:12 UTC 2018 , Edited by admin on Tue Mar 06 15:00:12 UTC 2018
PRIMARY
PUBCHEM
11753673
Created by admin on Tue Mar 06 15:00:12 UTC 2018 , Edited by admin on Tue Mar 06 15:00:12 UTC 2018
PRIMARY SWITZERF