revefenacin   Click here for help

GtoPdb Ligand ID: 10129

Synonyms: GSK-1160724 | GSK1160724 | TD4208 | Yupelri®
Approved drug
revefenacin is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Revefenacin (TD-4208) is a potent and long-acting muscarinic cholinergic receptor (mAChR) antagonist (LAMA) that has bronchodilatory effects [1-2], and which is approved for the management of chronic obstructive pulmonary disease (COPD). mAChR antagonists are the core agents used as first-line therapy for COPD. Revefenacin acts as a competitive antagonist at all 5 human mAChRs [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 108.21
Molecular weight 597.33
XLogP 4.08
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES O=C(Nc1ccccc1c1ccccc1)OC1CCN(CC1)CCN(C(=O)c1ccc(cc1)CN1CCC(CC1)C(=O)N)C
Isomeric SMILES O=C(Nc1ccccc1c1ccccc1)OC1CCN(CC1)CCN(C(=O)c1ccc(cc1)CN1CCC(CC1)C(=O)N)C
InChI 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)
1. Hegde SS, Pulido-Rios MT, Luttmann MA, Foley JJ, Hunsberger GE, Steinfeld T, Lee T, Ji Y, Mammen MM, Jasper JR. (2018)
Pharmacological properties of revefenacin (TD-4208), a novel, nebulized long-acting, and lung selective muscarinic antagonist, at human recombinant muscarinic receptors and in rat, guinea pig, and human isolated airway tissues.
Pharmacol Res Perspect, 6 (3): e00400. [PMID:29736245]
2. Pulido-Rios MT, McNamara A, Obedencio GP, Ji Y, Jaw-Tsai S, Martin WJ, Hegde SS. (2013)
In vivo pharmacological characterization of TD-4208, a novel lung-selective inhaled muscarinic antagonist with sustained bronchoprotective effect in experimental animal models.
J Pharmacol Exp Ther, 346 (2): 241-50. [PMID:23685545]
3. Quinn D, Barnes CN, Yates W, Bourdet DL, Moran EJ, Potgieter P, Nicholls A, Haumann B, Singh D. (2018)
Pharmacodynamics, pharmacokinetics and safety of revefenacin (TD-4208), a long-acting muscarinic antagonist, in patients with chronic obstructive pulmonary disease (COPD): Results of two randomized, double-blind, phase 2 studies.
Pulm Pharmacol Ther, 48: 71-79. [PMID:28987804]