eplerenone   

GtoPdb Ligand ID: 2876

Synonyms: Inspra® | SC-66110
eplerenone is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: Eplerenone is a potassium-sparing diuretic, which works by antagonising the effects of aldosterone.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: eplerenone

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 82.2
Molecular weight 414.2
XLogP 1.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C1CC2=CC(=O)CCC2(C23C1C1CCC4(C1(C)CC3O2)CCC(=O)O4)C
Isomeric SMILES COC(=O)[C@@H]1CC2=CC(=O)CC[C@@]2([C@@]23[C@@H]1[C@@H]1CC[C@]4([C@@]1(C)C[C@H]3O2)CCC(=O)O4)C
InChI InChI=1S/C24H30O6/c1-21-7-4-14(25)10-13(21)11-15(20(27)28-3)19-16-5-8-23(9-6-18(26)30-23)22(16,2)12-17-24(19,21)29-17/h10,15-17,19H,4-9,11-12H2,1-3H3/t15-,16+,17-,19+,21+,22+,23-,24-/m1/s1
InChI Key JUKPWJGBANNWMW-VWBFHTRKSA-N
References
1. Bell MG, Gernert DL, Grese TA, Belvo MD, Borromeo PS, Kelley SA, Kennedy JH, Kolis SP, Lander PA, Richey R et al.. (2007)
(S)-N-{3-[1-cyclopropyl-1-(2,4-difluoro-phenyl)-ethyl]-1H-indol-7-yl}-methanesulfonamide: a potent, nonsteroidal, functional antagonist of the mineralocorticoid receptor.
J. Med. Chem., 50 (26): 6443-5. [PMID:18038968]