Eplerenone

Iupac Name：methyl (1R,2S,9R,10R,11S,14R,15S,17R)-2,15-dimethyl-5,5'-dioxospiro[18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-ene-14,2'-oxolane]-9-carboxylate

CAS No.: 107724-20-9

Molecular Weight：414.498

Modify Date.: 2022-11-22 16:54

Introduction: Eplerenone is used alone or in combination with other medications to treat high blood pressure. Eplerenone is in a class of medications called mineralocorticoid receptor antagonists. It works by blocking the action of aldosterone, a natural substance in the body that raises blood pressure. View more+

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1. Names and Identifiers

1.1 Name: Eplerenone
1.2 Synonyms: (2'R,4aS,4bR,5aR,6aS,9aS,9bR,10R)-Methyl 4a,6a-diMethyl-2,4'-dioxo-3,4,4a,4',5a,5',6,6a,8,9,9a,9b,10,11-tetradecahydro-2H,3'H-spiro[cyclopenta[1,2]phenanthro[4,4a-b]oxirene-7,2'-furan]-10-carboxylate (4aS,4bR,5aR,6aS,7R,9aS,9bR,10R)-4a,6a-diméthyl-2,5'-dioxo-2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tétradécahydro-3H,3'H-spiro[cyclopenta[7,8]phénanthro[4b,5-b]oxirène-7,2'-furane]-10-carboxylate de méthyle (7α,11α,17α)-9,11-epoxy-17-hydroxy-3-oxo-γ-lactone-pregn-4-ene-7,21-dicarboxylic acid-7-methyl ester [107724-20-9] 9,11a-Epoxy-17-hydroxy-3-oxo-17a-pregn-4-ene-7a,21-dicarboxylic Acid g-Lactone Methyl Ester 9,11-epoxy-7-(methoxycarbonyl)-3-oxo-17-pregn-4-ene-21,17-carbolactone 9,11α-Epoxy-17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic Acid Γ-Lactone Methyl Ester 9,11α-Epoxy-17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, γ-lactone, methyl ester Elperenone Epleremone eplerenon Eplerenone [USAN] Eplerenone for system suitability Eplerenone intermediate Eplerenone EplerenoneC24H3006 EPLERINONE epoxymexrenone HSDB 7522 Inspra Methyl (4aS,4bR,5aR,6aS,7R,9aS,9bR)-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 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 Methyl (4aS,4bR,5aR,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 Methyl (4aS,4bR,6aS,7R,9aS,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 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]oxiren-7,2'-furan]-10-carboxylat MFCD07783647 plerenone Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)- Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, γ-lactone, methyl ester, (7α,11α,17α)- 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 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,7R,9aS,9bR)- 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,7R,9aS,9bR,10R)- 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,6aS,7R,9a S,10R)- 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,6aS,7R,9aS,10R)-

1.3 CAS No.: 107724-20-9

1.4 CID: 443872

1.5 EINECS(EC#): 600-850-8

1.6 Molecular Formula: C24H30O6 (isomer)

1.7 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

1.8 InChkey: JUKPWJGBANNWMW-VWBFHTRKSA-N

1.9 Canonical Smiles: CC12CCC(=O)C=C1CC(C3C24C(O4)CC5(C3CCC56CCC(=O)O6)C)C(=O)OC

1.10 Isomers Smiles: C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3[C@]24[C@H](O4)C[C@]5([C@H]3CC[C@@]56CCC(=O)O6)C)C(=O)OC

2. Properties

2.1 Density: 1.31

2.1 Melting point: 241-243oC

2.1 Boiling point: 597.9°Cat760mmHg

2.1 Refractive index: 1.587

2.1 Flash Point: 259.5°C

2.1 Precise Quality: 414.20400

2.1 PSA: 82.20000

2.1 logP: 3.12450

2.1 Solubility: DMSO: soluble2mg/mL, clear (warmed)

2.2 Λmax: 240nm(lit.)

2.3 Appearance: white to beige

2.4 Chemical Properties: Eplerenone is an odorless, white to off-white crystalline powder. It is very slightly soluble in water, with its solubility essentially pH-independent. The octanol/water partition coefficient of eplerenone is approximately 7.1 at pH 7.0.

2.5 Color/Form: White to off-white crystalline powder

2.6 Odor: Odorless

2.7 Physical: Solid

2.8 Water Solubility: DMSO: soluble2mg/mL, clear (warmed)

2.9 StorageTemp: Store at RT

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 3 companies. For more detailed information, please visit ECHA C&L website

Of the 2 notification(s) provided by 2 of 3 companies with hazard statement code(s):

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H317 (50%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H373 (50%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H413 (50%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P321, P322, P330, P333+P313, P363, P405, and P501

3.2 Methods of Manufacturing: Preparation: J. Grob, J. Kalvoda, EP 122232; eidem, US 4559332 (1984, 1985 both to Ciba-Geigy).

3.3 Usage: Selective aldosterone receptor antagonist (SARA), structurally similar to Spiranolactone. Eplerenone is used alone or in combination with other medications to treat high blood pressure. Eplerenone is in a class of medications called mineralocorticoid receptor antagonists. It works by blocking the action of aldosterone, a natural substance in the body that raises blood pressure.

4. Safety and Handling

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl eplerenone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = 7.1 at pH 7.0

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: 3077

4.4 Formulations/Preparations: Oral: Tablets, film-coated: 25 mg Inspra, (Pfizer), 50 mg Inspra, (Pfizer).
Epoxymexrenone

4.5 WGK Germany: 3

4.5 Specification: ?Eplerenone (CAS NO.107724-20-9), its Synonyms are 9,11alpha-Epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic acid, gamma-lactone, methyl ester ; Epoxymexrenone ; Inspra ; Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)- .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

107724-20-9Total: 12 Synthesis Route

95716-70-4 74 Suppliers

107724-20-9 298 Suppliers

Literatures:
PHARMACIA and UPJOHN COMPANY Patent: WO2005/92913 A1, 2005 ; Location in patent: Page/Page column 32-39 ;
Yield: ~82%

95716-72-6

107724-20-9 298 Suppliers

Literatures:
Helvetica Chimica Acta, , vol. 80, # 2 p. 566 - 585
Yield: null

95716-74-8 2 Suppliers

107724-20-9 298 Suppliers

Literatures:
Helvetica Chimica Acta, , vol. 80, # 2 p. 566 - 585
Yield: null

View all

8. Precursor and Product

precursor:

95716-72-6

124-41-4

188988-15-0

95716-74-8

67-56-1

192569-17-8

192704-58-8

209253-72-5

192704-54-4

1398078-09-5

1398078-03-9

95716-70-4

192704-56-6

95716-71-5

View all

9. Other Information

9.0 Storage Conditions: Preparation: J. Grob, J. Kalvoda, EP 122232; eidem, US 4559332 (1984, 1985 both to Ciba-Geigy).

9.1 Henrys Law Constant: Henry's Law constant = 4.9X10-14 atm-cu m/mol at 25 °C (est)

9.2 Experimental Properties: Hydroxyl radical reaction rate constant = 9.4X10-11 cu cm/molec-sec at 25 °C (est)|Ozone radical reaction rate constant = 1.13X10-17 cu cm/molec-sec at 25 °C (est)

9.3 Disposal Methods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

9.4 FDA Requirements: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl eplerenone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

9.5 Interactions: Lithium toxicity has been reported in patients receiving lithium concomitantly with diuretics and ACE inhibitors; serum lithium concentrations should be monitored if eplerenone is administered concomitantly with lithium.|Antihypertensive and/or diuretic effects may be potentiated when these medications /other hypotension-producing medications/ are used concurrently with eplerenone; although some antihypertensive and/or diuretic combinations are frequently used for therapeutic advantage, dosage adjustments may be necessary during concurrent use.|/Use of grapefruit juice with eplerenone/ may cause a small increase in exposure.|Concomitant use of potent inhibitors of CYP450 3A4 /including eltraconazole or ketoconazole/ with eplerenone is contraindicated.|For more Interactions (Complete) data for EPLERENONE (12 total), please visit the HSDB record page.

9.6 Populations At Special Risk: Patients with renal impairment are at an increased risk for developing hyperkalemia.|... 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, ... .

9.7 Livertox Summary: Eplerenone is an aldosterone receptor antagonist and potassium-sparing diuretic used in the therapy of hypertension. Eplerenone therapy has been associated with transient elevations in serum aminotransferase levels, but has yet to be linked to cases of clinically apparent drug induced liver disease.

9.8 Drug Classes: Diuretics

9.9 Therapeutic Uses: 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/|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.|... 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. ...

9.10 Drug Warnings: 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./|... 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, ... .|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.|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.|For more Drug Warnings (Complete) data for EPLERENONE (12 total), please visit the HSDB record page.

9.11 Absorption: Apparent plasma clearance: approximately 10 L/hr. Less than 5% is recovered as unchanged drug in the urine and feces. Renal: 67%. Fecal: 32%.|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.|Eplerenone is distributed into milk in rats; ... .|... 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.

9.12 Metabolism: Eplerenone metabolism is primarily mediated via CYP3A4. No active metabolites have been identified in human plasma.

9.13 Biological Half Life: Elimination: 4 to 6 hours.

9.14 Antidote: To decrease absorption: Eplerenone has been shown to bind extensively to charcoal. To enhance elimination: Eplerenone cannot be removed by hemodialysis. Monitoring: Monitor blood pressure, weight, and electrocardiogram. Patients should be monitored for fluid status and serum electrolytes (particularly sodium and potassium). Supportive care: Treatment should be symptomatic and supportive.|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

9.15 Human Toxicity Excerpts: /SIGNS AND SYMPTOMS/ The most likely manifestations of human overdosage would be hypotension or hyperkalemia.

9.16 Mesh Entry Terms: CGP 30083

9.17 Formulations: Oral: Tablets, film-coated: 25 mg Inspra, (Pfizer), 50 mg Inspra, (Pfizer).|Epoxymexrenone

10. Computational chemical data

Molecular Weight: 414.498g/mol
Molecular Formula: C₂₄H₃₀O₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 414.20423867
Monoisotopic Mass: 414.20423867
Complexity: 907
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 82.2
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAEgAAAaIAAAAwYIAABIAAAGDAAAAAGgAAAAAAD1SggAICCAAABACIAqDSCAAAAAAgAAAACAEAAEgAABIAAQACAAAEwAAIAQPK7PzPgAAAAAAAAADAAAYAADAAAYAADAAAAA==

11. Question & Answer

Pharmacology and Side Effects of Eplerenone May 17 2021
Aldosterone, the final product of the renin-angiotensin-aldosterone system (RAAS), is a mineralocorticoid hormone that classically acts, via the mineralocorticoid (aldosterone) receptor, on epithelia of the kidneys, colon, and sweat glands to maintain electrolyte homeostasis. Aldosterone has also b...

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