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: WARNINGRx-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 ;
	(verify)

Eplerenone, sold under the brand name Inspra, is an aldosterone antagonist type of potassium-sparing diuretic that is used to treat chronic heart failure and high blood pressure, particularly for people with resistant hypertension due to elevated aldosterone. It is a steroidal antimineralocorticoid of the spirolactone group and a selective aldosterone receptor antagonist (SARA).^[6]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ ^a ^b ^c ^d ^e Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 743–. ISBN 978-1-60913-345-0.
^ ^a ^b Sica DA (January 2005). "Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis". Heart Failure Reviews. 10 (1): 23–9. doi:10.1007/s10741-005-2345-1. PMID 15947888. S2CID 21437788.
^ Struthers A, Krum H, Williams GH (April 2008). "A comparison of the aldosterone-blocking agents eplerenone and spironolactone". Clinical Cardiology. 31 (4): 153–8. doi:10.1002/clc.20324. PMC 6652937. PMID 18404673.
^ Frishman WH, Cheng-Lai A, Nawarskas J (4 January 2005). Current Cardiovascular Drugs. Springer Science & Business Media. pp. 246–. ISBN 978-1-57340-221-7.
^ Delyani JA, Rocha R, Cook CS, Tobert DS, Levin S, Roniker B, et al. (2001). "Eplerenone: a selective aldosterone receptor antagonist (SARA)". Cardiovascular Drug Reviews. 19 (3): 185–200. doi:10.1111/j.1527-3466.2001.tb00064.x. PMID 11607037.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[LemkeWilliams2012-2] Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 743–. ISBN 978-1-60913-345-0.

[Sica2005-3] Sica DA (January 2005). "Pharmacokinetics and pharmacodynamics of mineralocorticoid blocking agents and their effects on potassium homeostasis". Heart Failure Reviews. 10 (1): 23–9. doi:10.1007/s10741-005-2345-1. PMID 15947888. S2CID 21437788.

[StruthersKrum2008-4] Struthers A, Krum H, Williams GH (April 2008). "A comparison of the aldosterone-blocking agents eplerenone and spironolactone". Clinical Cardiology. 31 (4): 153–8. doi:10.1002/clc.20324. PMC 6652937. PMID 18404673.

[FrishmanCheng-Lai2005-5] Frishman WH, Cheng-Lai A, Nawarskas J (4 January 2005). Current Cardiovascular Drugs. Springer Science & Business Media. pp. 246–. ISBN 978-1-57340-221-7.

[DelyaniRocha2006-6] Delyani JA, Rocha R, Cook CS, Tobert DS, Levin S, Roniker B, et al. (2001). "Eplerenone: a selective aldosterone receptor antagonist (SARA)". Cardiovascular Drug Reviews. 19 (3): 185–200. doi:10.1111/j.1527-3466.2001.tb00064.x. PMID 11607037.

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