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Eplerenone
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Name

Eplerenone

 EINECS 600-850-8
CAS No. 107724-20-9 Density 1.31 g/cm3
PSA 82.20000 LogP 3.12450
Solubility N/A Melting Point 241-243 °C
Formula C24H30O6 Boiling Point 597.933 °C at 760 mmHg
Molecular Weight 414.499 Flash Point 259.474 °C
Transport Information N/A Appearance White solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 107724-20-9 (Eplerenone) Hazard Symbols N/A
Synonyms

Pregn-4-ene-7,21-dicarboxylic acid,9,11-epoxy-17-hydroxy-3-oxo-,?- lactone,methyl ester,(7R,11R,17R)-;9,11alpha-Epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic acid, gamma-lactone, methyl ester;Cgp 30083;Epoxymexrenone;SC-66110;Inspra;Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)-;Eplerenone(& the intermediates);Inspra (TN);Pregn-4-ene-7,21-dicarboxylic acid,9,11-epoxy-17-hydroxy-3-oxo-γ,-lactone,methyl ester,(7a,11a,17a);Pregn-4-ene-7,21-dicarboxylic acid,9,11-epoxy-17-hydroxy-3-oxo-,?- lactone,methyl ester,(7R,11R,17R)-;

Article Data 12

Eplerenone Synthetic route

95716-70-4

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

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%
192704-58-8

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

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
67-56-1

methanol

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

124-41-4

sodium methylate

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
67-56-1

methanol

C24H27NO5

107724-20-9

eplerenone

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

Δ9(11)-canrenone

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
188988-15-0

C23H30O4

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
95716-72-6

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

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
95716-74-8

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

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
67-56-1

methanol

C24H27NO5

124-41-4

sodium methylate

107724-20-9

eplerenone

Conditions
ConditionsYield
for 23.5h; Heating / reflux;
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

B

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

D

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

E

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
...Expand

Eplerenone Specification

1. Introduction of Eplerenone

Eplerenone, with its systematic name of 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, is one kind of white crystalline powder. Its Classification Code are including Aldosterone antagonist; Aldosterone antagonists; Antihypertensive; Hormone Antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists.

2. Properties of Eplerenone

Eplerenone has the following datas: (1)Index of Refraction: 1.587; (2)Molar Refractivity: 106.122 cm3; (3)Molar Volume: 315.658 cm3; (4)Surface Tension: 53.062 dyne/cm; (5)Density: 1.313 g/cm3; (6)Flash Point: 259.474 °C; (7)Enthalpy of Vaporization: 89.051 kJ/mol; (8)Boiling Point: 597.933 °C at 760 mmHg; (9)Vapour Pressure: 0 mmHg at 25 °C; (10)Melting Point: 241-243 °C.

3. Use of Eplerenone

Eplerenone is an aldosterone antagonist used as an adjunct in the management of chronic heart failure. Eplerenone is used alone or in combination with other medications to treat high blood pressure.Common adverse drug reactions associated with the use of Eplerenone include: hyperkalaemia, hypotension, dizziness, altered renal function, and increased creatinine concentration.

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