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| CAS No.: | 107724-20-9 |
|---|---|
| Name: | Eplerenone |
| Article Data: | 12 |
| Molecular Structure: | |
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| Formula: | C24H30O6 |
| Molecular Weight: | 414.499 |
| 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)-; |
| EINECS: | 600-850-8 |
| Density: | 1.31 g/cm3 |
| Melting Point: | 241-243 °C |
| Boiling Point: | 597.933 °C at 760 mmHg |
| Flash Point: | 259.474 °C |
| Appearance: | White solid |
| PSA: | 82.20000 |
| LogP: | 3.12450 |
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- 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With dipotassium hydrogenphosphate; dihydrogen peroxide | 82% |
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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
E
- 107724-20-9
eplerenone
| Conditions | Yield |
|---|---|
| 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 |
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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.