Eplerenone

Eplerenone
Clinical data
Pronunciation	/ɛpˈlɛrənoʊn/
Trade names	Inspra, others
Other names	SC-66110; CGP-30083; 9-11α-Epoxymexrenone; 9,11α-Epoxy-7α-methoxycarbonyl-3-oxo-17α-pregn-4-ene-21,17-carbolactone
AHFS/Drugs.com	Monograph
MedlinePlus	a603004
License data	US DailyMed: Eplerenone;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth (tablets)
ATC code	C03DA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	~70%
Protein binding	~50% (33–60%) (primarily to α1-acid glycoprotein)
Metabolism	Liver (CYP3A4)
Metabolites	6β-OH-EPL, 6β,21-OH-EPL, 21-OH-EPL, 3α,6β-OH-EPL (All inactive)
Elimination half-life	4–6 hours
Excretion	Urine (67%), feces (32%)
Identifiers
	IUPAC name methyl (4aS,4bR,5aR,6aS,7R,9aS,9bR,10R)-4a,6a-dimethyl-2,5'-dioxo-2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tetradecahydro-3H,3'H-spiro[cyclopenta[7,8]phenanthro[4b,5-b]oxirene-7,2'-furan]-10-carboxylate;
CAS Number	107724-20-9 ;
PubChem CID	5282131;
IUPHAR/BPS	2876;
DrugBank	DB00700 ;
ChemSpider	10203511 ;
UNII	6995V82D0B;
KEGG	D01115 ;
ChEBI	CHEBI:31547 ;
ChEMBL	ChEMBL1095097 ;
PDB ligand	YNU (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID2046094 ;
ECHA InfoCard	100.106.615
Chemical and physical data
Formula	C24H30O6
Molar mass	414.498 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)[C@@H]4C\C1=C\C(=O)CC[C@]1(C)[C@@]65O[C@@H]6C[C@@]3(C)[C@@H](CC[C@]23CCC(=O)O2)[C@H]45;
	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 ; Key:JUKPWJGBANNWMW-VWBFHTRKSA-N ;
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Eplerenone, marketed under brand name Inspa or Espler, is an aldosterone antagonist used primarily in the treatment of heart failure with reduced ejection fraction (HFrEF), particularly following myocardial infarction. It may also be considered as an add-on therapy in resistant hypertension; however, the majority of evidence in this setting supports the use of spironolactone (another drug in a same class), with fewer studies directly evaluating eplerenone.

It is also a steroidal antimineralocorticoid of the spirolactone group and a selective aldosterone receptor antagonist (SARA).