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[8.8.0.01,17.02,7.011,15]octadecan]-6'-ene-9'-carboxylate

• ChemBase ID: 154403
• Molecular Formular: C24H30O6
• Molecular Mass: 414.4914
• Monoisotopic Mass: 414.20423868
• SMILES: C[C@]12CCC(=O)C=C1C[C@H]([C@@H]1[C@@]32[C@H](O3)C[C@]2([C@H]1CC[C@]12CCC(=O)O1)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1CC2=CC(=O)CC[C@@]2([C@@]23[C@@H]1[C@@H]1CC[C@]4([C@@]1(C)C[C@H]3O2)CCC(=O)O4)C
• 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
• InChIKey: JUKPWJGBANNWMW-VWBFHTRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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,^1^7.0^2,^7.0^1^1,^1^5]octadecan]-6'-ene-9'-carboxylate
• IUPAC Traditional name: eplerenone
• Synonyms: 9,11alpha-Epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic acid, gamma-lactone, methyl ester; Cgp 30083; Eplerenone [USAN]; Epoxymexrenone; HSDB 7522; Inspra; Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)-; SC-66110; Eplerenone; Eplerenone

Database IDs

• CAS Number: 107724-20-9
• PubChem SID: 162248542
• PubChem CID: 443872

CALCULATED PROPERTIES

• Acid pKa: 15.113572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.3314128
• LogD (pH = 7.4): 2.3314128
• Log P: 2.3314128
• Molar Refractivity: 106.6777 cm^3
• Polarizability: 42.67 Å^3
• Polar Surface Area: 82.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble2 mg/mL, clear (warmed); H2O: insoluble
• Apperance: white to beige powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 95+%; 97%
• Empirical Formula (Hill Notation): C24H30O6

DETAILS

Sigma Aldrich - E6657

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.