Eplerenone (CED0003453)

Record Information
Version1.0
Creation Date2016-05-22 05:29:12 UTC
Update Date2026-08-22 03:52:26 UTC
Accession NumberCHEM018728
Identification
Common NameEplerenone
ClassSmall Molecule
Description
Eplerenone is an organic compound with the formula C24H30O6 and an average molecular weight of 414.49 g/mol. Eplerenone belongs to the steroid lactones, a subclass of steroids and steroid derivatives within the organic compounds. It acts as an antagonist of the mineralocorticoid receptor (NR3C2). This compound is found in or released from four recorded sources, including diuretics within healthcare, pharmaceuticals, and veterinary products, line transmission systems in electrical and electronic equipment, and other smoking requisites and non-electric simulated smoking devices in household cleaning and consumer products. The recorded exposure route for eplerenone is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
EpoxymexrenoneChEBI
InspraChEBI
9,11-Epoxy-7-(methoxycarbonyl)-3-oxo-17-pregn-4-ene-21,17-carbolactoneHMDB
EplerenonHMDB
Chemical FormulaC24H30O6
Average Molecular Mass414.491 g/mol
Monoisotopic Mass414.204 g/mol
CAS Registry Number107724-20-9
IUPAC Namemethyl (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
Traditional Nameeplerenone
SMILES[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC
InChI IdentifierInChI=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
InChI KeyJUKPWJGBANNWMW-VWBFHTRKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSpironolactones and derivatives
Alternative Parents
Substituents
  • Spironolactone
  • Cyclohexenone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Ether
  • Oxirane
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP1.67ALOGPS
logP2.33ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)15.11ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area82.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.68 m³·mol⁻¹ChemAxon
Polarizability43.79 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0adu-0209000000-12b60f587e43aa45d6d6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009400000-ea48b83fadcea11b59c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aos-0109000000-7c2b34b32e47c8b99347Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4955000000-4a2bd122f48c88a31213Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0006900000-58cc006a22b6e44336a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xr-0009400000-8706c8ed2bc60109596eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-7019000000-4c8e14c579aa065c04c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0001900000-0eaf4de79ce0afc4b997Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0119300000-db12e4174bf5f8367cd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-1329000000-ac3a3b5b248711145827Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0003900000-5fb3fe537cffeaf693e8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0007900000-431de4fbbae9c6ab1882Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-e64b0b7d685ef47232f3Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
588.0Log mg/kg[330:1000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
290DiureticsHealthcare, pharmaceuticals & veterinary productsNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Eplerenone Action Pathway (Old)
Eplerenone Action Pathway (Old)
Eplerenone Action Pathway
Eplerenone Action Pathway
Eplerenone Drug Metabolism Action Pathway
Eplerenone Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)4.7488
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)1.63483
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)5.44945
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)4.43741
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)7.08428
Click to view 3D structureMineralocorticoid receptorP22199Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)21.7199
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)11.7552
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)21.0193
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)21.0193
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)128.451
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)18.2946
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)146.357
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansPredicted (SEA)55.1172
Click to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 1P18405HumansPredicted (SEA)13.0787
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)2871.31
Click to view 3D structure11-beta-hydroxysteroid dehydrogenase type 2P80365HumansPredicted (SEA)18.9174
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)15.6477
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)7.94062
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)17.7496
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)2112.91
Click to view 3D structureSolute carrier organic anion transporter family member 1A1P46720Rattus norvegicusPredicted (SEA)17.2047
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)352.501
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)2456.14
Click to view 3D structureSolute carrier family 22 member 3O88446Rattus norvegicusPredicted (SEA)16.504
Concentrations
Not Available
External Links
DrugBank IDDB00700
HMDB IDHMDB0014838
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEplerenone
Chemspider ID10203511
ChEBI ID31547
PubChem Compound ID443872
Kegg Compound IDC12512
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM