methyl (1'R,2R,2'S,9'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate

• ChemBase ID: 582
• Molecular Formular: C24H30O6
• Molecular Mass: 414.4914
• Monoisotopic Mass: 414.20423868
• SMILES: O1[C@@]23C([C@H]4[C@](CC12)([C@@]1(OC(=O)CC1)CC4)C)[C@@H](CC1=CC(=O)CC[C@]31C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1CC2=CC(=O)CC[C@@]2([C@@]23C1[C@@H]1CC[C@]4([C@@]1(C)CC3O2)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-MKKQDWMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1'R,2R,2'S,9'R,11'S,15'S)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0^{1,17}.0^{2,7}.0^{11,15}]octadecan]-6'-ene-9'-carboxylate
• IUPAC Traditional name: inspra
• Brand Name: INSPRA
• Synonyms: Epoxymexrenone; Eplerenone

Database IDs

• CAS Number: 107724-20-9
• PubChem SID: 160964045
• PubChem CID: 150310

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.67
• LOG S: -4.66
• Solubility (Water): 9.03e-03 g/l

PROPERTIES

Physical Property

• Solubility: Slightly soluble
• Hydrophobicity(logP): 1.3

DETAILS

DrugBank - DB00700

• Drug Groups: approved
• Description: 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.
• Indication: For improvement of survival of stable patients with left ventricular systolic dysfunction (ejection fraction <40%) and clinical evidence of congestive heart failure after an acute myocardial infarction.
• Pharmacology: 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.
• Toxicity: The most likely symptoms of human overdosage would be anticipated to be hypotension or hyperkalemia. However, no cases of human overdosage with eplerenone have been reported.
• Affected Organisms: Humans and other mammals
• Biotransformation: Eplerenone is metabolized primarily by CYP3A4, however, no active metabolites have been identified in human plasma.
• Absorption: The absolute bioavailability of eplerenone is unknown.
• Half Life: 4-6 hours
• Protein Binding: 50%
• Distribution: * 43 to 90 L
• Clearance: * Apparent plasma cl=10 L/hr
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com