darifenacin   Click here for help

GtoPdb Ligand ID: 321

Synonyms: Emselex® | Enablex® | UK-88525
Approved drug
darifenacin is an approved drug (EMA & FDA (2004))
Compound class: Synthetic organic
Comment: Darifenacin is a muscarinic acetylcholine M3 receptor antagonist.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: darifenacin

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 55.56
Molecular weight 426.23
XLogP 4.54
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES NC(=O)C(c1ccccc1)(c1ccccc1)C1CCN(C1)CCc1ccc2c(c1)CCO2
Isomeric SMILES NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(C1)CCc1ccc2c(c1)CCO2
InChI InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1
1. Gillberg PG, Sundquist S, Nilvebrant L. (1998)
Comparison of the in vitro and in vivo profiles of tolterodine with those of subtype-selective muscarinic receptor antagonists.
Eur J Pharmacol, 349 (2-3): 285-92. [PMID:9671109]
2. Hirose H, Aoki I, Kimura T, Fujikawa T, Numazawa T, Sasaki K, Sato A, Hasegawa T, Nishikibe M, Mitsuya M et al.. (2001)
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
J Pharmacol Exp Ther, 297 (2): 790-7. [PMID:11303071]
3. Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A et al.. (2010)
AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder.
Br J Pharmacol, 160 (5): 1119-27. [PMID:20590605]