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1. 9,11-epoxy-7-(methoxycarbonyl)-3-oxo-17-pregn-4-ene-21,17-carbolactone
2. Eplerenon
3. Inspra
1. Epoxymexrenone
2. Inspra
3. 107724-20-9
4. Sc-66110
5. Selara
6. Epleremone
7. Cgp 30083
8. Cgp-30083
9. Chembl1095097
10. Chebi:31547
11. Sc-6611o
12. 6995v82d0b
13. Ncgc00159559-02
14. Dsstox_cid_26094
15. Dsstox_rid_81333
16. Dsstox_gsid_46094
17. (+)-eplerenone
18. Eplerenone [usan]
19. 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[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate
20. Methyl (1'r,2s,2's,9'r,10'r,11's,15's,17'r)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate
21. Inspra (tn)
22. Cas-107724-20-9
23. Hsdb 7522
24. Eplerenone [usan:inn:ban]
25. Unii-6995v82d0b
26. Eplerenone- Bio-x
27. Sc 6110
28. Eplerenone [mi]
29. Eplerenone [inn]
30. Eplerenone [jan]
31. Eplerenone [hsdb]
32. Eplerenone [vandf]
33. Eplerenone [mart.]
34. Eplerenone [usp-rs]
35. Eplerenone [who-dd]
36. Schembl21515
37. 9,11alpha-epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic Acid, Gamma-lactone, Methyl Ester
38. Gtpl2876
39. Dtxsid2046094
40. Eplerenone (jp17/usan/inn)
41. Eplerenone [orange Book]
42. Eplerenone, >=98% (hplc)
43. Eplerenone [ep Monograph]
44. Hms3413k08
45. Hms3677k08
46. Hy-b0251
47. Zinc3985982
48. Tox21_111746
49. Bdbm50318300
50. Mfcd05662207
51. S1707
52. Akos015962307
53. Tox21_111746_1
54. Ac-4213
55. Ccg-268820
56. Db00700
57. Ks-1406
58. 7alpha-methoxycarbonyl-3-oxo-9,11alpha-epoxy-17alpha-pregn-4-ene-21,17-carbolactone
59. Ncgc00159559-03
60. Be164415
61. Pregn-4-ene-7,21-dicarboxylic Acid, 9,11-epoxy-17-hydroxy-3-oxo-, Gamma-lactone, Methyl Ester, (7alpha,11alpha,17alpha)-
62. Spiro(cyclopenta(7,8)phenanthro(4b,5-b)oxirene-7(3h),2'(3'h)-furan)-10-carboxylic Acid, 2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tetradecahydro-4a,6a-dimethyl-2,5'-dioxo-, Methyl Ester, (4as,4br,5ar,6as,7 R,9as,9br,10r)-
63. E0905
64. D01115
65. Ab01274707-01
66. Ab01274707_02
67. A895400
68. Q423804
69. Sr-01000942233
70. Sr-01000942233-1
71. Methyl Dimethyl-5'-dioxo-spiro[[?]-[?],2'-tetrahydrofuran]carboxylate
72. (7?,11?,17?)-9,11-epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic Acid ?-lactone Methyl Ester
73. 9,11.alpha.-epoxy-17-hydroxy-3-oxo-17.alpha.-pregn-4-ene-7.alpha.,21-dicarboxylic Acid, .gamma.-lactone, Methyl Ester
74. 9,11alpha-epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic Acid Gamma-lactone Methyl Ester
75. Pregn-4-ene-7,21-dicarboxylic Acid, 9,11-epoxy-17-hydroxy-3-oxo-, G-lactone, Methyl Ester, (7.alpha.,11.alpha.,17.alpha)-
76. Ynu
| Molecular Weight | 414.5 g/mol |
|---|---|
| Molecular Formula | C24H30O6 |
| XLogP3 | 1.4 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Exact Mass | 414.20423867 g/mol |
| Monoisotopic Mass | 414.20423867 g/mol |
| Topological Polar Surface Area | 82.2 Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 907 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 8 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Eplerenone |
| PubMed Health | Eplerenone (By mouth) |
| Drug Classes | Cardiovascular Agent |
| Drug Label | Eplerenone tablets contain eplerenone, a blocker of aldosterone binding at the mineralocorticoid receptor. Eplerenone is chemically described as Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, -lactone, methyl ester, (7,11,17... |
| Active Ingredient | Eplerenone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 25mg; 50mg |
| Market Status | Prescription |
| Company | Apotex; Sandoz |
| 2 of 4 | |
|---|---|
| Drug Name | Inspra |
| PubMed Health | Eplerenone (By mouth) |
| Drug Classes | Cardiovascular Agent |
| Drug Label | INSPRA contains eplerenone, a blocker of aldosterone binding at the mineralocorticoid receptor. Eplerenone is chemically described as Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, -lactone, methyl ester, (7,11,17)-. Its em... |
| Active Ingredient | Eplerenone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 25mg; 50mg |
| Market Status | Prescription |
| Company | Gd Searle |
| 3 of 4 | |
|---|---|
| Drug Name | Eplerenone |
| PubMed Health | Eplerenone (By mouth) |
| Drug Classes | Cardiovascular Agent |
| Drug Label | Eplerenone tablets contain eplerenone, a blocker of aldosterone binding at the mineralocorticoid receptor. Eplerenone is chemically described as Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, -lactone, methyl ester, (7,11,17... |
| Active Ingredient | Eplerenone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 25mg; 50mg |
| Market Status | Prescription |
| Company | Apotex; Sandoz |
| 4 of 4 | |
|---|---|
| Drug Name | Inspra |
| PubMed Health | Eplerenone (By mouth) |
| Drug Classes | Cardiovascular Agent |
| Drug Label | INSPRA contains eplerenone, a blocker of aldosterone binding at the mineralocorticoid receptor. Eplerenone is chemically described as Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, -lactone, methyl ester, (7,11,17)-. Its em... |
| Active Ingredient | Eplerenone |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 25mg; 50mg |
| Market Status | Prescription |
| Company | Gd Searle |
Eplerenone is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive drugs. /Included in US product labeling/
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
Inspra is indicated to improve survival of stable patients with left ventricular systolic dysfunction (ejection fraction less than or equal to 40%) and clinical evidence of congestive heart failure after an acute myocardial infarction.
Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 2537
... Eplerenone should replace spironolactone as a natriuretic and antikaliuretic in heart failure and as add-on treatment in severe systolic cardiac insufficiency, and it is indicated after an acute myocardial infarction complicated by left ventricular dysfunction and heart failure. The finding that hypertension control with diuretic-based pharmacotherapy results in better prevention of heart failure than pressure reduction with other drugs makes it pertinent to investigate whether diuretics in general, and eplerenone in particular, should constitute part of the initial pharmacotherapy for heart failure when there is no overt fluid retention and independent of the etiology. ...
PMID:15733814 Reyes AJ et al; Eur J Intern Med 16 (1): 3-11 (2005)
FDA Pregnancy Risk Category: B /NO EVIDENCE OF RISK IN HUMANS. Adequate, well controlled studies in pregnant women have not shown increased risk of fetal abnormalities despite adverse findings in animals, or, in the absence of adequate human studies, animal studies show no fetal risk. The chance of fetal harm is remote but remains a possibility./
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1246
... When used for hypertension, the drug is contraindicated in patients with type 2 diabetes mellitus with microalbuminuria, serum creatinine concentrations exceeding 2 or 1.8 mg/dL in males or females, respectively, creatinine clearance less than 50 mL/minute, ... .
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 1979
The most serious risk associated with eplerenone therapy is hyperkalemia (serum potassium greater than 5.5 mEq/L), which may cause serious, sometimes fatal, cardiac arrhythmias. Patients with impaired renal function or diabetes mellitus and patients receiving concurrent agents affecting the renin-angiotensin-aldosterone system (e.g., angiotensin-converting enzyme (ACE) inhibitors, angiotensin II receptor antagonists) are at an increased risk for developing hyperkalemia. Eplerenone should be used with caution in patients with congestive heart failure following an acute myocardial infarction, who have renal impairment (i.e., serum creatinine concentrations exceeding 2 or 1.8 mg/dL in males or females, respectively, or creatinine clearance of 50 mL/minute or less) or those with diabetes mellitus (including those with proteinuria). Serum potassium concentrations should be monitored periodically in patients receiving eplerenone. Dosage reduction has been shown to decrease serum potassium concentrations.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 1979
Adverse effects reported in 1% or more of patients receiving eplerenone for the management of hypertension are dizziness, fatigue, flu-like symptoms, cough, diarrhea, abdominal pain, hyperkalemia, decreased serum sodium concentrations, abnormal vaginal bleeding, gynecomastia, hypercholesterolemia, hypertriglyceridemia, mastodynia, or albuminuria.
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 1979
For more Drug Warnings (Complete) data for EPLERENONE (12 total), please visit the HSDB record page.
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.
FDA Label
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.
Mineralocorticoid Receptor Antagonists
Drugs that bind to and block the activation of MINERALOCORTICOID RECEPTORS by MINERALOCORTICOIDS such as ALDOSTERONE. (See all compounds classified as Mineralocorticoid Receptor Antagonists.)
Antihypertensive Agents
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)
C03DA04
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
C - Cardiovascular system
C03 - Diuretics
C03D - Aldosterone antagonists and other potassium-sparing agents
C03DA - Aldosterone antagonists
C03DA04 - Eplerenone
Absorption
The absolute bioavailability of eplerenone is unknown.
Volume of Distribution
43 to 90 L
Clearance
Apparent plasma cl=10 L/hr
Apparent plasma clearance: approximately 10 L/hr. Less than 5% is recovered as unchanged drug in the urine and feces. Renal: 67%. Fecal: 32%.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
Mean peak plasma concentrations of eplerenone are reached approximately 1.5 hours following oral administration. The absolute bioavailability of eplerenone is unknown. Both peak plasma levels (Cmax) and area under the curve (AUC) are dose proportional for doses of 25 to 100 mg and less than proportional at doses above 100 mg. The plasma protein binding of eplerenone is about 50% and it is primarily bound to alpha 1-acid glycoproteins. The apparent volume of distribution at steady state ranged from 43 to 90 L. Eplerenone does not preferentially bind to red blood cells.
Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 2536
Eplerenone is distributed into milk in rats; ... .
McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 1979
... Preclinical data show that eplerenone and/or metabolites are present in rat breast milk (0.85:1 [milk:plasma] AUC ratio) obtained after a single oral dose. Peak concentrations in plasma and milk were obtained from 0.5 to 1 hour after dosing.
Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 2538
Eplerenone is metabolized primarily by CYP3A4, however, no active metabolites have been identified in human plasma.
Eplerenone metabolism is primarily mediated via CYP3A4. No active metabolites have been identified in human plasma.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
Eplerenone has known human metabolites that include 21-hydroxyeplerenone and 6beta-hydroxyeplerenone.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
4-6 hours
Elimination: 4 to 6 hours.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
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.
Eplerenone has relative selectivity in binding to recombinant human mineralocorticoid receptors compared to its binding to recombinant human glucocorticoid, progesterone, and androgen receptors.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
Eplerenone has been shown to produce sustained increases in plasma renin and serum aldosterone, consistent with the inhibition of the negative regulatory feedback of aldosterone on renin secretion. The resulting increased plasma renin activity and aldosterone circulation levels do not overcome the effect of eplerenone on blood pressure.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
Eplerenone binds to the mineralocorticoid receptor and blocks the binding of aldosterone, a component of the renin-angiotensin-aldosterone-system (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, brain) tissues and increases blood pressure through induction of sodium resorption and possibly other mechanisms.
Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1245
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USFDA APPLICATION NUMBER - 21437
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