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编号: 582
• 分子式: C24H30O6
• 平均质量: 414.4914
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: inspra
• 商标名: INSPRA
• 别名: Epoxymexrenone; Eplerenone

登记号

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

理论计算性质

JChem

• Acid pKa: 15.113572
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 2.3314128
• LogD (pH = 7.4): 2.3314128
• Log P: 2.3314128
• 摩尔折射率: 106.6777 cm^3
• 极化性: 42.67 Å^3
• 极化表面积: 82.2 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.67
• LOG S: -4.66
• 溶解度: 9.03e-03 g/l

分子性质

理化性质

• 溶解度: Slightly soluble
• 疏水性(logP): 1.3

详细说明

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