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107724-20-9

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107724-20-9 Usage

Description

Different sources of media describe the Description of 107724-20-9 differently. You can refer to the following data:
1. 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.
2. Eplerenone is a mineralocorticoid receptor antagonist. It is selective for the mineralocorticoid receptor over glucocorticoid, androgen, progesterone, and estrogen receptors in radioligand binding assays (IC50s = 138, 6,920, 523, >10,000, and 5,702 nM, respectively). Eplerenone inhibits aldosterone-induced mineralocorticoid activity in a luciferase assay (IC50 = 122 nM). In vivo, eplerenone (100 mg/kg per day) reduces urinary albumin secretion and glomerulosclerosis in the Dahl salt-sensitive rat model of hypertension and nephropathy. It reduces myocardial IL-1β levels and collagen deposition, as well as improves left ventricular systolic dysfunction in a mouse model of acute myocardial infarction. Formulations containing eplerenone have been used in the treatment of hypertension and heart failure after myocardial infarction.
3. Eplerenone derives its antihypertensive effect by blocking the binding of aldosterone at the mineralocorticoid receptor (MR). The drug, which was previously approved only for the oral treatment of hypertension, is now indicated to improve survival of stable patients with left ventricular systolic dysfunction (ejection fraction <40%) and clinical evidence congestive heart failure (CHF) after an acute myocardial infarction. Aldosterone is a key hormone in the renin-angiotensin-aldosterone system (RAAS), which is of critical importance in the development and progression of hypertension, cardiac remodeling and other cardiovascular diseases. The purpose of RAAS is to control sodium, potassium, and fluid volume balance. Aldosterone binds to MRs 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. The actions of aldosterone can be blocked by spironolactone (Aldactone ?), a relatively nonselective MR antagonist that has been used in clinical practice for many years. Eplerenone, a structural analog of spironolactone, is a highly selective MR antagonist, with significantly lower affinity for other nuclear receptors. It can be prepared by several related ways, with the key step being the introduction of 11-a-hydroxy group on the steroid scaffold via microbiological conversion. The presence of the 11-a-hydroxy group permits the derivation of the epoxy functionality found in eplerenone. Following oral administration, eplerenone is well absorbed and reaches peak plasma concentrations in~2 h. The bioavailability of eplerenone is 98% and it is cleared predominantly by CYP3A4 metabolism, with an elimination half-life of 4–6 h. Steady state is reached within two days. Eplerenone therapy is typically initiated with 25 mg once daily oral dosing and, if tolerated by the patient, titrated to 50 mg once daily. In a clinical study, eplerenone significantly reduced deaths in congestive heart failure patients after a heart attack, above and beyond standard therapy, including ACE inhibitors and β-blockers. The trial in more than 6600 hospitalized patients demonstrated a 15% reduction in the risk of death for eplerenone compared with placebo, in addition to standard treatment. The most commonly reported adverse events associated with eplerenone are hyperkalemia and increased creatine.

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.

Biological activity

Eplerenone belongs to a class of drugs called aldosterone antagonists. A class of drugs is a group of medications that work in a similar way. These drugs are often used to treat similar conditions. Eplerenone works by interfering with the activity of a steroid in your body called aldosterone. Aldosterone acts to increase the amount of sodium and water you retain. This increased sodium and water can cause high blood pressure, which can in turn cause heart failure.

Interactions

Eplerenone is primarily metabolized by the cytochrome P450 enzyme CYP3A4. Thus the potential exists for adverse drug interactions with other drugs that induce or inhibit CYP3A4. Specifically, the concomitant use of the CYP3A4 potent inhibitors ketoconazole and itraconazole is contraindicated. Other CYP3A4 inhibitors including erythromycin, saquinavir, and verapamil should be used with caution. Other drugs that increase potassium concentrations may increase the risk of hyperkalemia associated with eplerenone therapy, including salt substitutes, potassium supplements and other potassium-sparing diuretics.

Overview

Eplerenone is in a class of medications called mineralocorticoid receptor antagonists. It can be used individually or in combination with other medications to treat hypertension by blocking the action of aldosterone, a natural substance in the body that raises blood pressure.

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.

Mechanism of action

Aldosterone,with many physiological and pathological effects, can cause central blood pressure and endothelial injury (catecholamines enhance its role), reduce heart rate variability, induce ventricular arrhythmias, and promote retention of sodium, potassium and magnesium loss, promote myocardial fibrosis, necrosis and inflammation, damage the fibrinolytic system. Angiotensin converting enzyme inhibitors (also called angiotensin converting enzyme inhibitors, referred to as ACEI) and angiotensin Ⅱ receptor antagonist ARB aldosterone can inhibit the secretion of adrenaline, but after a period of treatment.The release of aldosterone was restored,which may even exceed the baseline plasma concentration levels. Despite adequate treatment of ACEI and ARB, aldosterone-induced damage can still happen, so it is necessary to use aldosterone receptor antagonists in the treatment of hypertension. Clinical studies have shown that patients who are not satisfied with the efficacy of ACEI or ARB therapy can add eplerenone along with the treatment. Non-selective aldosterone receptor antagonist spironolactone can reduce mortality in patients with congestive heart failure, However, the side effects of male hyperplasia and other diseases associated with sex hormones have limited its application in the treatment of hypertension.

Adverse effects

Common adverse drug reactions (ADRs) associated with the use of eplerenone include: hyperkalaemia, hypotension, dizziness, altered renal function, and increased creatinine concentration.

References

https://en.wikipedia.org/wiki/Eplerenone https://medlineplus.gov/druginfo/meds/a603004.html http://www.rxlist.com/inspra-drug.htm

Chemical Properties

White Solid

Originator

Ciba-Geigy (Novartis) (US)

Uses

Different sources of media describe the Uses of 107724-20-9 differently. You can refer to the following data:
1. 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.
2. Eplerenone is an aldosterone antagonist with an IC50 of 0.36 μM. It is used as an adjunct in the management of chronic heart failure. It is similar to the diuretic spironolactone, though it may be more specific for the mineralocorticoid receptor and is sp
3. anticancer agent

Brand name

Inspra (Searle).

General Description

Eplerenone, 9,11α-epoxy-17α-hydroxy-3-oxopregn-4-ene-7α,21-dicarboxylic acid, γ-lactone,methyl ester (Inspra), is a newer aldosterone antagonist that isused for the treatment of hypertension.

Biological Activity

Selective mineralocorticoid (aldosterone) receptor antagonist (IC 50 = 360 nM). Displays > 27-fold selectivity over androgen, progesterone and estrogen receptors (IC 50 > 10 μ M). Orally active antihypertensive in vivo .

Biochem/physiol Actions

Eplerenone is an aldosterone antagonist more specific for the mineralocorticoid receptor than spironolactone (S3378), having lower affinity for progesterone, androgen, and glucocorticoid receptors.

Clinical Use

A newer drug, eplerenone, has a structure similar to that of spironolactone and a similar mechanism of action. It was initially approved for use in the treatment of hypertension but it can now be used in the treatment of patients with left ventricular systolic dysfunction and congestive heart failure after myocardial infarction.

Drug interactions

Potentially hazardous interactions with other drugsACE inhibitors or AT-II antagonists: enhanced hypotensive effect; risk of severe hyperkalaemia.Anti-arrhythmics: concentration increased by amiodarone - reduce eplerenone dose.amiodarone - reduce eplerenone dose. Antibacterials: concentration increased by clarithromycin and telithromycin - avoid; concentration increased by erythromycin - reduce eplerenone dose; concentration reduced by rifampicin - avoid; avoid with lymecycline; increased risk of hyperkalaemia with trimethoprim.Antidepressants: concentration reduced by St John’s wort - avoid; increased risk of postural hypotension with tricyclics; enhanced hypotensive effect with MAOIs.Antiepileptics: concentration reduced by carbamazepine, fosphenytoin, phenytoin, phenobarbital and primidone - avoid.Antifungals: concentration increased by itraconazole and ketoconazole - avoid; concentration increased by fluconazole - reduce eplerenone dose.Antihypertensives: enhanced hypotensive effect, increased risk of first dose hypotensive effect with post-synaptic alpha-blockers.Antivirals: concentration increased by ritonavir - avoid; concentration increased by saquinavir - reduce eplerenone doseCiclosporin: increased risk of hyperkalaemia and nephrotoxicityCytotoxics: increased risk of nephrotoxicity and ototoxicity with platinum compounds.NSAIDs: increased risk of hyperkalaemia (especially with indometacin); increased risk of nephrotoxicity; antagonism of diuretic effect.Potassium salts: increased risk of hyperkalaemia.Lithium: reduced lithium excretion - avoidTacrolimus: increased risk of hyperkalaemia and nephrotoxicity.CYP3A4 inhibitors: Do not exceed a dose of 25 mg daily for eplerenone.CYP3A4 inducers: reduced eplerenone concentration - avoid.

Metabolism

Eplerenone metabolism is primarily mediated via CYP3A4. No active metabolites of eplerenone have been identified in human plasma. Less than 5% of an eplerenone dose is recovered as unchanged drug in the urine and faeces. Following a single oral dose of radiolabelled drug, approximately 32% of the dose was excreted in the faeces and approximately 67% was excreted in the urine

Check Digit Verification of cas no

The CAS Registry Mumber 107724-20-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,7,7,2 and 4 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 107724-20:
(8*1)+(7*0)+(6*7)+(5*7)+(4*2)+(3*4)+(2*2)+(1*0)=109
109 % 10 = 9
So 107724-20-9 is a valid CAS Registry Number.
InChI:InChI=1/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

107724-20-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (E0905)  Eplerenone  >98.0%(HPLC)

  • 107724-20-9

  • 200mg

  • 1,250.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001704)  Eplerenone  EuropePharmacopoeia (EP) Reference Standard

  • 107724-20-9

  • Y0001704

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001706)  Eplerenone for peak identification  EuropePharmacopoeia (EP) Reference Standard

  • 107724-20-9

  • Y0001706

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001705)  Eplerenone for system suitability  EuropePharmacopoeia (EP) Reference Standard

  • 107724-20-9

  • Y0001705

  • 1,880.19CNY

  • Detail
  • USP

  • (1237553)  Eplerenone  United States Pharmacopeia (USP) Reference Standard

  • 107724-20-9

  • 1237553-250MG

  • 4,647.24CNY

  • Detail

107724-20-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name eplerenone

1.2 Other means of identification

Product number -
Other names Elperenone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:107724-20-9 SDS

107724-20-9Synthetic route

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester
95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; trichloroacetamide; dihydrogen peroxide In dichloromethane at 0 - 15℃; for 24h; pH=9;98%
With trichloroacetamide; dihydrogen peroxide; potassium acetate In dichloromethane at 10 - 15℃; for 0.75h; Temperature;91.3%
With potassium phosphate; trichloroacetamide; dihydrogen peroxide In dichloromethane at 20℃;85.3%
methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone
192704-58-8

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; dihydrogen peroxide82%
Multi-step reaction with 2 steps
1: potassium formate; formic acid / acetic anhydride / 100 °C
2: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
methanol
67-56-1

methanol

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile
192704-54-4

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile

sodium methylate
124-41-4

sodium methylate

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Stage #1: methanol; 4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile; sodium methylate for 20.25h; Heating / reflux;
Stage #2: With hydrogenchloride In methanol; water Heating / reflux;
Stage #3: With dipotassium hydrogenphosphate; formic acid; dihydrogen peroxide; potassium formate; acetic anhydride; methanesulfonyl chloride; triethylamine; trichloroacetonitrile more than 3 stages;
27.1%
Stage #1: methanol; 4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile; sodium methylate at 67℃; for 16 - 20h;
Stage #2: With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 0.75h;
Stage #3: With dipotassium hydrogenphosphate; formic acid; dihydrogen peroxide; potassium formate; acetic anhydride; trichloroacetonitrile more than 3 stages;
7.2 g
methanol
67-56-1

methanol

C24H27NO5

C24H27NO5

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 24h; Heating / reflux;20%
Δ9(11)-canrenone
95716-71-5

Δ9(11)-canrenone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 g / AlEt3 / hexane; tetrahydrofuran / 0.5 h / Heating
2: 6.9 g / DIBAH / 1,2-dimethoxy-ethane; hexane / 2 h / 5 °C
3: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C
4: 2.7 g / CH2Cl2; diethyl ether / 0.17 h
5: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C
View Scheme
Multi-step reaction with 5 steps
1.1: boron trifluoride diethyl etherate / tetrahydrofuran / -10 °C
2.1: N-Bromosuccinimide; potassium carbonate / tetrahydrofuran; water / 35 °C
3.1: ozone / dichloromethane; isopropyl alcohol / -20 °C
3.2: 20 °C
4.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C
5.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C
View Scheme
C23H30O4
188988-15-0

C23H30O4

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C
2: 2.7 g / CH2Cl2; diethyl ether / 0.17 h
3: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C
View Scheme
17β-hydroxy-7α-cyano-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
95716-72-6

17β-hydroxy-7α-cyano-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 6.9 g / DIBAH / 1,2-dimethoxy-ethane; hexane / 2 h / 5 °C
2: 6.6 g / aq. CrO3, H2SO4 / acetone / 0.5 h / 5 °C
3: 2.7 g / CH2Cl2; diethyl ether / 0.17 h
4: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C
View Scheme
17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone
95716-74-8

17β-hydroxypregna-4,9(11)-dien-3-one-7α,21-dicarboxylic acid γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.7 g / CH2Cl2; diethyl ether / 0.17 h
2: 71.6 percent / aq. H2O2, (CCl3CO)2O / CH2Cl2 / 1.5 h / below 4 deg C
View Scheme
methanol
67-56-1

methanol

C24H27NO5

C24H27NO5

sodium methylate
124-41-4

sodium methylate

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
for 23.5h; Heating / reflux;
17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester
95716-70-4

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

A

7-methyl hydrogen 17-hydroxy-3,12-dioxo-17α-pregna-4,9(11)-diene-7α,21-dicarboxylate, γ-lactone

7-methyl hydrogen 17-hydroxy-3,12-dioxo-17α-pregna-4,9(11)-diene-7α,21-dicarboxylate, γ-lactone

B

7-methyl hydrogen 12α,17-dihydroxy-3-oxo-17α-pregna-4,9(11)-diene-7α,21-dicarboxylate, γ-lactone

7-methyl hydrogen 12α,17-dihydroxy-3-oxo-17α-pregna-4,9(11)-diene-7α,21-dicarboxylate, γ-lactone

C

7-methyl hydrogen 4α,5α:9α,11α-diepoxy,17-hydroxy-3-oxo-17α-pregnane-7α,21-dicarboxylate, γ-lactone

7-methyl hydrogen 4α,5α:9α,11α-diepoxy,17-hydroxy-3-oxo-17α-pregnane-7α,21-dicarboxylate, γ-lactone

D

7-methyl hydrogen 9α,11β,17-trihydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylate, γ-lactone

7-methyl hydrogen 9α,11β,17-trihydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylate, γ-lactone

E

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetonitrile In dichloromethane; water at 8 - 10℃; for 23h;A n/a
B 123 mg
C n/a
D 46.7 mg
E 3.16 g
C23H28O6

C23H28O6

eplerenone
107724-20-9

eplerenone

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
1398078-03-9

11β,17β-dihydroxy-7α-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
1.2: 4 h
2.1: potassium carbonate / 0 - 20 °C
3.1: triethylamine / dichloromethane / 0 °C
4.1: potassium formate; formic acid / acetic anhydride / 100 °C
5.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
1.2: 4 h
2.1: potassium carbonate / acetone / 0 - 20 °C
3.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
4.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
5.1: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9
View Scheme
11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
1398078-09-5

11β,17β-dihydroxy-7β-nitromethyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone
192704-56-6

11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 °C
2: potassium formate; formic acid / acetic anhydride / 100 °C
3: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuryl dichloride; 1H-imidazole / tetrahydrofuran / 1.5 h / -10 - 20 °C
2: trichloroacetamide; disodium hydrogenphosphate; dihydrogen peroxide / dichloromethane / 18 h / 15 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
3: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9
View Scheme
9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone
209253-72-5

9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / 0 - 20 °C
2: triethylamine / dichloromethane / 0 °C
3: potassium formate; formic acid / acetic anhydride / 100 °C
4: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 0 - 20 °C
2: triethylamine / dichloromethane / 3 h / 0 - 20 °C
3: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
4: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9
View Scheme
11α-hydroxyl canrenone
192569-17-8

11α-hydroxyl canrenone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / 0 - 20 °C
4.1: triethylamine / dichloromethane / 0 °C
5.1: potassium formate; formic acid / acetic anhydride / 100 °C
6.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
2.1: potassium carbonate; benzalkonium chloride; nitromethane / N,N-dimethyl-formamide / 48 h / 90 °C
3.1: acetic acid / N,N-dimethyl-formamide / 0.5 h / 45 °C
3.2: 4 h
4.1: potassium carbonate / 0 - 20 °C
5.1: triethylamine / dichloromethane / 0 °C
6.1: potassium formate; formic acid / acetic anhydride / 100 °C
7.1: trichloroacetamide; dihydrogen peroxide; dipotassium hydrogenphosphate / dichloromethane / 10 - 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate; benzalkonium chloride / N,N-dimethyl-formamide / 48 h / 90 - 100 °C
2.1: sodium nitrite / N,N-dimethyl-formamide / 1.5 h / 45 °C
2.2: 4 h
3.1: potassium carbonate / acetone / 0 - 20 °C
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: acetic anhydride; potassium formate; formic acid / 19 h / 70 - 100 °C / Inert atmosphere
6.1: dipotassium hydrogenphosphate; dihydrogen peroxide; trichloroacetamide / dichloromethane / 24 h / 0 - 15 °C / pH 9
View Scheme
9(11)-encanrenone
41850-21-9

9(11)-encanrenone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: boron trifluoride diethyl etherate / acetonitrile / 4 h / -25 - -20 °C / Inert atmosphere
2: potassium carbonate; 5,5-dibromohydantoin / tetrahydrofuran; water / 20 °C / Inert atmosphere
3: ozone / -50 °C
4: trichloroacetamide; potassium phosphate; dihydrogen peroxide / dichloromethane / 20 °C
View Scheme
17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone
610785-40-5

17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate; 5,5-dibromohydantoin / tetrahydrofuran; water / 20 °C / Inert atmosphere
2: ozone / -50 °C
3: trichloroacetamide; potassium phosphate; dihydrogen peroxide / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide; potassium carbonate / tetrahydrofuran; water / 35 °C
2.1: ozone / dichloromethane; isopropyl alcohol / -20 °C
2.2: 20 °C
3.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C
4.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C
View Scheme
7a-(1,4-dicarbonylpentenyl)-9(11)-encanrenone

7a-(1,4-dicarbonylpentenyl)-9(11)-encanrenone

eplerenone
107724-20-9

eplerenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ozone / dichloromethane; isopropyl alcohol / -20 °C
1.2: 20 °C
2.1: potassium hydrogencarbonate / tetrahydrofuran / 10 °C
3.1: dipotassium hydrogenphosphate; 2-chloro-2,2-difluoroacetamide; dihydrogen peroxide / toluene / 55 °C
View Scheme
eplerenone
107724-20-9

eplerenone

9,11α-epoxy-17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, γ-lactone

9,11α-epoxy-17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, γ-lactone

Conditions
ConditionsYield
Stage #1: eplerenone With sodium hydroxide In water; acetonitrile at 25 - 90℃; for 66.67h; Heating / reflux;
Stage #2: With sulfuric acid In water; acetonitrile
67%
Multi-step reaction with 2 steps
1: lithium hydroxide / water / 48 h
2: hydrogenchloride / water
View Scheme
eplerenone
107724-20-9

eplerenone

A

9,11α-epoxy-7β-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

9,11α-epoxy-7β-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

B

9,11α-epoxy-7-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

9,11α-epoxy-7-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

Conditions
ConditionsYield
With sodium methylate In methanol for 24h; Reflux;A 49%
B 0.55 g
eplerenone
107724-20-9

eplerenone

9,11α-epoxy,17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, dipotassium salt

9,11α-epoxy,17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, dipotassium salt

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane; water at 25 - 70℃; for 6h;0.55 g
eplerenone
107724-20-9

eplerenone

9,11α-epoxy,17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, disodium salt

9,11α-epoxy,17-hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid, disodium salt

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 70℃; for 0.666667h;
eplerenone
107724-20-9

eplerenone

9,11α-epoxy-7β-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

9,11α-epoxy-7β-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone

Conditions
ConditionsYield
With sodium methylate In methanol at 50 - 65℃; for 16.5h; Heating / reflux;400 mg
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

eplerenone
107724-20-9

eplerenone

7-methyl hydrogen 9,11α-epoxy-3-ethoxy-17-hydroxy-17α-pregn-4-ene-7α,21-dicarboxylate, γ-lactone

7-methyl hydrogen 9,11α-epoxy-3-ethoxy-17-hydroxy-17α-pregn-4-ene-7α,21-dicarboxylate, γ-lactone

Conditions
ConditionsYield
Stage #1: orthoformic acid triethyl ester; eplerenone; toluene-4-sulfonic acid In ethanol at 20℃; for 0.5h;
Stage #2: With pyridine; sodium acetate In ethanol
33.8 g
eplerenone
107724-20-9

eplerenone

C47H42O10
1621954-04-8

C47H42O10

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / water / 48 h
2: hydrogenchloride / water
3: dmap; dicyclohexyl-carbodiimide
View Scheme
eplerenone
107724-20-9

eplerenone

C23H30O7
1621954-05-9

C23H30O7

Conditions
ConditionsYield
With lithium hydroxide In water for 48h;

107724-20-9Downstream Products

107724-20-9Relevant articles and documents

A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone

Zhang, Bin,Chen, Hongli,Tang, Huanyu,Feng, Huijin,Li, Yuanchao

, p. 1086 - 1091 (2012)

A novel and efficient method of stereoselectively introducing α-nitromethyl group to C-7 position of 11α-hydroxyl canrenone 4 was described. In addition, this method was successfully applied in a total synthesis of Eplerenone 8. The route was characteristic of simple operation, moderate reaction conditions with 5 steps and 55% total yield, at the same time, without any expensive or toxic reagent in use.

Method for synthesizing 7a-methyl formate-9(11)-encanrenone

-

, (2020/05/01)

The invention discloses a method for synthesizing 7a-methyl formate-9(11)-encanrenone. The method comprises the following steps: reacting 9(11)-encanrenone used as a raw material with 2-methylfuran atfirst, performing ring opening by using dibromohydantoin, rearranging, ozonizing, adding a metal reducing agent to methanol or a mixed solution of methanol and other solvent, and performing reducingesterification to directly obtain the 7a-methyl formate-9(11)-encanrenone. The method has the advantages of operation step simplification, high yield, simplicity in operation, few three wastes, and suitableness for industrial production.

A steroid compound derivative having, its preparation process and its use in the preparation of Eplerenone

-

Paragraph 0094-0103, (2020/05/05)

The invention relates to a canrenone derivative steroid compound, a preparation method and an application in the medicine field, and particularly relates to 7alpha-nitro methyl-11alpha,17beta-dihydroxy-3-oxo-17alpha-pregna-4-ene-21-carboxylic acid-gamma-lactone (a compound shown in formula 2), a preparation method and an application in eplerenone preparation. The key steps of the invention are that nitromethane is used as a nucleophilic reagent; the alpha-nitro methyl group is introduced to the C-7 position stereoselectively so as to further construct a carboxylic acid methyl ester structure with a C-7alpha position configuration of eplerenone; the method of the invention has the characteristics of short steps, mild conditions, and low cost.

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