Eplerenone
Identification
- Name
- Eplerenone
- Accession Number
- DB00700
- Description
Eplerenone, an aldosterone receptor antagonist similar to spironolactone, has been shown to produce sustained increases in plasma renin and serum aldosterone, consistent with inhibition of the negative regulatory feedback of aldosterone on renin secretion. The resulting increased plasma renin activity and aldosterone circulating levels do not overcome the effects of eplerenone. Eplerenone selectively binds to recombinant human mineralocorticoid receptors relative to its binding to recombinant human glucocorticoid, progesterone and androgen receptors.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Eplerenone (DB00700)
- Weight
- Average: 414.4914
Monoisotopic: 414.204238692 - Chemical Formula
- C24H30O6
- Synonyms
- Eplerenona
- Eplerenone
- Epoxymexrenone
- External IDs
- SC-66110
- SC-6611O
Pharmacology
- Indication
For improvement of survival of stable patients with left ventricular systolic dysfunction (ejection fraction <40%) and clinical evidence of congestive heart failure after an acute myocardial infarction.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Eplerenone, an aldosterone receptor antagonist similar to spironolactone, has been shown to produce sustained increases in plasma renin and serum aldosterone, consistent with inhibition of the negative regulatory feedback of aldosterone on renin secretion. The resulting increased plasma renin activity and aldosterone circulating levels do not overcome the effects of eplerenone. Eplerenone selectively binds to recombinant human mineralocorticoid receptors relative to its binding to recombinant human glucocorticoid, progesterone and androgen receptors.
- Mechanism of action
Eplerenone binds to the mineralocorticoid receptor and thereby blocks the binding of aldosterone (component of the renin-angiotensin-aldosterone-system, or RAAS). Aldosterone synthesis, which occurs primarily in the adrenal gland, is modulated by multiple factors, including angiotensin II and non-RAAS mediators such as adrenocorticotropic hormone (ACTH) and potassium. Aldosterone binds to mineralocorticoid receptors in both epithelial (e.g., kidney) and nonepithelial (e.g., heart, blood vessels, and brain) tissues and increases blood pressure through induction of sodium reabsorption and possibly other mechanisms.
Target Actions Organism AMineralocorticoid receptor antagonistHumans - Absorption
The absolute bioavailability of eplerenone is unknown.
- Volume of distribution
- 43 to 90 L
- Protein binding
50%
- Metabolism
Eplerenone is metabolized primarily by CYP3A4, however, no active metabolites have been identified in human plasma.
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
4-6 hours
- Clearance
- Apparent plasma cl=10 L/hr
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
The most likely symptoms of human overdosage would be anticipated to be hypotension or hyperkalemia. However, no cases of human overdosage with eplerenone have been reported.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Eplerenone Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Eplerenone may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abametapir The serum concentration of Eplerenone can be increased when it is combined with Abametapir. Abatacept The metabolism of Eplerenone can be increased when combined with Abatacept. Acalabrutinib The metabolism of Eplerenone can be decreased when combined with Acalabrutinib. Acarbose Eplerenone may increase the excretion rate of Acarbose which could result in a lower serum level and potentially a reduction in efficacy. Acebutolol The risk or severity of hyperkalemia can be increased when Eplerenone is combined with Acebutolol. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Eplerenone. Acemetacin The therapeutic efficacy of Eplerenone can be decreased when used in combination with Acemetacin. Acetaminophen Eplerenone may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy. Acetyldigitoxin Eplerenone may decrease the excretion rate of Acetyldigitoxin which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid grapefruit products. Grapefruit juice may increase the serum levels of eplerenone by 25% by inhibiting CYP3A4.
- Take with or without food.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataInspra Tablet, film coated 50 mg/1 Oral Physicians Total Care, Inc. 2004-04-14 2011-06-30 US 
Inspra Tablet 25 mg Oral Upjohn Canada Ulc 2009-05-08 Not applicable Canada 
Inspra Tablet, film coated 50 mg/1 Oral G.D. Searle LLC Division of Pfizer Inc 2002-09-27 Not applicable US Inspra Tablet 25 mg/1 Oral Rebel Distributors 2002-09-27 Not applicable US Inspra Tablet, film coated 25 mg/1 Oral G.D. Searle LLC Division of Pfizer Inc 2002-09-27 Not applicable US Inspra Tablet 50 mg Oral Upjohn Canada Ulc 2009-05-05 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-eplerenone Tablet Oral Apotex Corporation Not applicable Not applicable Canada Apo-eplerenone Tablet Oral Apotex Corporation Not applicable Not applicable Canada Eplerenone Tablet, film coated 25 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-10-03 Not applicable US Eplerenone Tablet 50 mg/1 Oral Apotex Corp 2008-07-30 2019-03-31 US Eplerenone Tablet 25 mg/1 Oral Physicians Total Care, Inc. 2009-09-14 Not applicable US Eplerenone Tablet 25 mg/1 Oral Eon Labs, Inc. 2008-08-01 Not applicable US Eplerenone Tablet, film coated 25 mg/1 Oral American Health Packaging 2019-05-08 Not applicable US Eplerenone Tablet, film coated 25 mg/1 Oral Breckenridge Pharmaceutical, Inc. 2018-09-18 Not applicable US Eplerenone Tablet, film coated 50 mg/1 Oral Greenstone LLC 2002-09-27 Not applicable US Eplerenone Tablet 25 mg/1 Oral Upsher-Smith Laboratories, LLC 2015-03-16 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- C03DA04 — Eplerenone
- Drug Categories
- Agents causing hyperkalemia
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Cardiovascular Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Diuretics
- Fused-Ring Compounds
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hypotensive Agents
- Lactones
- Mineralocorticoid (Aldosterone) Receptor Antagonists
- Mineralocorticoid Receptor Antagonists
- Natriuretic Agents
- Potassium-Sparing Diuretics
- Pregnanes
- Pregnenes
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Steroid lactones
- Direct Parent
- Spironolactones and derivatives
- Alternative Parents
- Oxepanes / Cyclohexenones / Gamma butyrolactones / Dicarboxylic acids and derivatives / Tetrahydrofurans / Methyl esters / Oxacyclic compounds / Epoxides / Dialkyl ethers / Organic oxides show 1 more
- Substituents
- Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Gamma butyrolactone show 13 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- 3-oxo steroid, epoxide, methyl ester, gamma-lactone, oxaspiro compound, steroid acid ester (CHEBI:31547)
Chemical Identifiers
- UNII
- 6995V82D0B
- CAS number
- 107724-20-9
- InChI Key
- JUKPWJGBANNWMW-VWBFHTRKSA-N
- 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
- IUPAC Name
- methyl (1'R,2R,2'S,9'R,10'R,11'S,15'S,17'R)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0¹,¹⁷.0²,⁷.0¹¹,¹⁵]octadecan]-6'-ene-9'-carboxylate
- SMILES
- [H][[email protected]@]12CC[[email protected]@]3(CCC(=O)O3)[[email protected]@]1(C)C[[email protected]]1O[[email protected]@]11[[email protected]@]2([H])[[email protected]@H](CC2=CC(=O)CC[[email protected]]12C)C(=O)OC
References
- Synthesis Reference
Bhaskar Reddy Guntoori, Svetoslav S. Bratovanov, Mohamed Ibrahim Zaki, Elena Bejan, Stephen E. Horne, "Process for the preparation and purification of eplerenone." U.S. Patent US20080234478, issued September 25, 2008.
US20080234478- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014838
- KEGG Drug
- D01115
- KEGG Compound
- C12512
- PubChem Compound
- 443872
- PubChem Substance
- 46509053
- ChemSpider
- 10203511
- BindingDB
- 50318300
- 298869
- ChEBI
- 31547
- ChEMBL
- CHEMBL1095097
- ZINC
- ZINC000003985982
- Therapeutic Targets Database
- DAP000085
- PharmGKB
- PA164749044
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- YNU
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Eplerenone
- AHFS Codes
- 24:32.20 — Mineralocorticoid (Aldosterone) Receptor Antagonists
- PDB Entries
- 5mwy
- FDA label
- Download (136 KB)
- MSDS
- Download (68.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Chronic Central Serous Chorioretinopathy 1 4 Completed Basic Science Metabolic Syndromes 1 4 Completed Basic Science Pharmacodynamics 1 4 Completed Prevention Chronic Renal Failure (CRF) 1 4 Completed Prevention Myocardial Infarction 1 4 Completed Treatment Atrial Switch Procedure / Transposition of the Great Vessels 1 4 Completed Treatment Chronic Central Serous Chorioretinopathy 1 4 Completed Treatment Congestive Heart Failure (CHF) 1 4 Completed Treatment Congestive Heart Failure (CHF) / Diastole 1 4 Completed Treatment Heart Failure / Left Ventricular Dysfunction 1
Pharmacoeconomics
- Manufacturers
- Apotex inc
- Sandoz inc
- Gd searle llc
- Packagers
- Apotex Inc.
- Eon Labs
- GD Searle LLC
- Greenstone LLC
- Pfizer Inc.
- Physicians Total Care Inc.
- Sandoz
- Dosage Forms
Form Route Strength Tablet, coated 25 mg Tablet, coated 50 mg Tablet, film coated Oral 25 MG Tablet, film coated Oral 50 MG Tablet Oral 50 mg/1 Tablet, coated Oral 25 mg Tablet, coated Oral 50 mg Tablet Oral Tablet Oral 25 MG Tablet Oral 25 mg/1 Tablet Oral 50 MG Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet - Prices
Unit description Cost Unit Inspra 25 mg tablet 4.87USD tablet Inspra 50 mg tablet 4.87USD tablet Eplerenone 25 mg tablet 4.18USD tablet Eplerenone 50 mg tablet 4.18USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6863902 No 2005-03-08 2020-10-10 US US6410054 Yes 2002-06-25 2020-06-08 US US6410524 Yes 2002-06-25 2020-05-05 US US6495165 Yes 2002-12-17 2020-06-08 US US6534093 Yes 2003-03-18 2020-06-08 US US6558707 Yes 2003-05-06 2020-06-08 US US6747020 Yes 2004-06-08 2020-05-05 US US7157101 Yes 2007-01-02 2020-06-08 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Slightly soluble Not Available logP 1.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00903 mg/mL ALOGPS logP 1.67 ALOGPS logP 2.33 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 15.11 ChemAxon pKa (Strongest Basic) -4.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 82.2 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 106.68 m3·mol-1 ChemAxon Polarizability 43.79 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9839 Blood Brain Barrier + 0.8556 Caco-2 permeable + 0.5076 P-glycoprotein substrate Substrate 0.7017 P-glycoprotein inhibitor I Inhibitor 0.8166 P-glycoprotein inhibitor II Inhibitor 0.8066 Renal organic cation transporter Non-inhibitor 0.7209 CYP450 2C9 substrate Non-substrate 0.8229 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Substrate 0.7407 CYP450 1A2 substrate Non-inhibitor 0.6978 CYP450 2C9 inhibitor Non-inhibitor 0.7982 CYP450 2D6 inhibitor Non-inhibitor 0.931 CYP450 2C19 inhibitor Non-inhibitor 0.839 CYP450 3A4 inhibitor Non-inhibitor 0.8368 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8902 Ames test Non AMES toxic 0.7496 Carcinogenicity Non-carcinogens 0.9441 Biodegradation Not ready biodegradable 0.9891 Rat acute toxicity 2.4761 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9453 hERG inhibition (predictor II) Non-inhibitor 0.7742
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
- Gene Name
- NR3C2
- Uniprot ID
- P08235
- Uniprot Name
- Mineralocorticoid receptor
- Molecular Weight
- 107066.575 Da
References
- Moore TD, Nawarskas JJ, Anderson JR: Eplerenone: a selective aldosterone receptor antagonist for hypertension and heart failure. Heart Dis. 2003 Sep-Oct;5(5):354-63. [PubMed:14503934]
- Fraccarollo D, Galuppo P, Hildemann S, Christ M, Ertl G, Bauersachs J: Additive improvement of left ventricular remodeling and neurohormonal activation by aldosterone receptor blockade with eplerenone and ACE inhibition in rats with myocardial infarction. J Am Coll Cardiol. 2003 Nov 5;42(9):1666-73. [PubMed:14607457]
- Rogerson FM, Yao Y, Smith BJ, Fuller PJ: Differences in the determinants of eplerenone, spironolactone and aldosterone binding to the mineralocorticoid receptor. Clin Exp Pharmacol Physiol. 2004 Oct;31(10):704-9. [PubMed:15554912]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Cook CS, Berry LM, Kim DH, Burton EG, Hribar JD, Zhang L: Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: differential metabolism by CYP3A4 and CYP3A5. Drug Metab Dispos. 2002 Dec;30(12):1344-51. [PubMed:12433801]
- McGraw J, Cherney M, Bichler K, Gerhardt A, Nauman M: The Relative Role of CYP3A4 and CYP3A5 in Eplerenone Metabolism. Toxicol Lett. 2019 Aug 10. pii: S0378-4274(19)30218-8. doi: 10.1016/j.toxlet.2019.08.003. [PubMed:31408697]
- Eplenerone FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Cook CS, Berry LM, Kim DH, Burton EG, Hribar JD, Zhang L: Involvement of CYP3A in the metabolism of eplerenone in humans and dogs: differential metabolism by CYP3A4 and CYP3A5. Drug Metab Dispos. 2002 Dec;30(12):1344-51. [PubMed:12433801]
- McGraw J, Cherney M, Bichler K, Gerhardt A, Nauman M: The Relative Role of CYP3A4 and CYP3A5 in Eplerenone Metabolism. Toxicol Lett. 2019 Aug 10. pii: S0378-4274(19)30218-8. doi: 10.1016/j.toxlet.2019.08.003. [PubMed:31408697]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid 11-beta-monooxygenase activity
- Specific Function
- Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
- Gene Name
- CYP11B2
- Uniprot ID
- P19099
- Uniprot Name
- Cytochrome P450 11B2, mitochondrial
- Molecular Weight
- 57559.62 Da
References
- Kobayashi N, Yoshida K, Nakano S, Ohno T, Honda T, Tsubokou Y, Matsuoka H: Cardioprotective mechanisms of eplerenone on cardiac performance and remodeling in failing rat hearts. Hypertension. 2006 Apr;47(4):671-9. doi: 10.1161/01.HYP.0000203148.42892.7a. Epub 2006 Feb 27. [PubMed:16505212]
Drug created on June 13, 2005 07:24 / Updated on October 19, 2020 07:46
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