Eplerenone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Eplerenone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Eplerenone?

The molecule Eplerenone presents a molecular formula of C24H30O6 and its IUPAC name is methyl (1R,2S,9R,10R,11S,14R,15S,17R)-2,15-dimethyl-5,5'-dioxospiro[18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-ene-14,2'-oxolane]-9-carboxylate.

Eplerenone (INN, trade name Inspra) is a medication used to treat hypertension and congestive heart failure. It is a selective aldosterone receptor antagonist..

Aldosterone is a hormone that regulates salt and water balance in the body. It is produced by the adrenal glands. When aldosterone levels are high, the body retains salt and water. This can lead to high blood pressure and fluid retention..

Eplerenone works by blocking the effects of aldosterone. This helps to lower blood pressure and reduce fluid retention..

Eplerenone is typically used in combination with other blood pressure medications. It is not recommended for use in people with severe kidney disease or liver disease..

Common side effects of eplerenone include headache, dizziness, and fatigue. Eplerenone can also cause low blood potassium levels. This can lead to muscle weakness, irregular heartbeat, and other problems..

Eplerenone is a prescription medication. It exists as an oral tablet..

Eplerenone is a safe and effective medication for treating hypertension and congestive heart failure. However, it is important to take it as directed by your doctor. Be sure to follow all instructions on your prescription label..

3D structure

Cartesian coordinates

Geometry of Eplerenone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Eplerenone JUKPWJGBANNWMW-VWBFHTRKSA-N chemical compound 2D structure molecule svg
Eplerenone

 

Molecule descriptors

 
IUPAC namemethyl (1R,2S,9R,10R,11S,14R,15S,17R)-2,15-dimethyl-5,5'-dioxospiro[18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-ene-14,2'-oxolane]-9-carboxylate
InChI codeInChI=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
SMILESCOC(=O)[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-Eplerenone
  • (7?,11?,17?)-9,11-Epoxy-17-hydroxy-3-oxo-pregn-4-ene-7,21-dicarboxylic acid ?-lactone methyl ester
  • 107724-20-9
  • 6995V82D0B
  • 7alpha-methoxycarbonyl-3-oxo-9,11alpha-epoxy-17alpha-pregn-4-ene-21,17-carbolactone
  • 9,11.ALPHA.-EPOXY-17-HYDROXY-3-OXO-17.ALPHA.-PREGN-4-ENE-7.ALPHA.,21-DICARBOXYLIC ACID, .GAMMA.-LACTONE, METHYL ESTER
  • 9,11alpha-Epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic Acid gamma-Lactone Methyl Ester
  • 9,11alpha-Epoxy-17-hydroxy-3-oxo-17alpha-pregn-4-ene-7alpha,21-dicarboxylic acid, gamma-lactone, methyl ester
  • A895400
  • AB01274707-01
  • AB01274707_02
  • AC-4213
  • BDBM50318300
  • BE164415
  • CCG-268820
  • CGP-30083
  • Cgp 30083
  • D01115
  • DB00700
  • DSSTox_CID_26094
  • DSSTox_GSID_46094
  • DSSTox_RID_81333
  • E0905
  • Epleremone
  • Eplerenone
  • Eplerenone (JP17/USAN/INN)
  • Eplerenone- Bio-X
  • Epoxymexrenone
  • GTPL2876
  • HMS3413K08
  • HMS3677K08
  • HSDB 7522
  • HY-B0251
  • Inspra
  • KS-1406
  • MFCD05662207
  • NCGC00159559-02
  • NCGC00159559-03
  • PREGN-4-ENE-7,21-DICARBOXYLIC ACID, 9,11-EPOXY-17-HYDROXY-3-OXO-, G-LACTONE, METHYL ESTER, (7.ALPHA.,11.ALPHA.,17.ALPHA)-
  • Pregn-4-ene-7,21-dicarboxylic acid, 9,11-epoxy-17-hydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)-
  • Q423804
  • SC 6110
  • SC-66110
  • SC-6611O
  • SR-01000942233
  • SR-01000942233-1
  • Selara
  • Spiro(cyclopenta(7,8)phenanthro(4b,5-b)oxirene-7(3H),2'(3'H)-furan)-10-carboxylic acid, 2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tetradecahydro-4a,6a-dimethyl-2,5'-dioxo-, methyl ester, (4aS,4bR,5aR,6aS,7 R,9aS,9bR,10R)-
  • YNU
  • methyl dimethyl-5'-dioxo-spiro[[?]-[?],2'-tetrahydrofuran]carboxylate
  • s1707

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3985982
  • CAS-107724-20-9
  • UNII-6995V82D0B
  • AKOS015962307
  • DTXSID2046094
  • CHEMBL1095097
  • CHEBI:31547
  • Tox21_111746
  • Tox21_111746_1
  • SCHEMBL21515

Physico-Chemical properties

IUPAC namemethyl (1R,2S,9R,10R,11S,14R,15S,17R)-2,15-dimethyl-5,5'-dioxospiro[18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadec-6-ene-14,2'-oxolane]-9-carboxylate
Molecular formulaC24H30O6
Molecular weight414.491
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity107.74
LogP3.1
Topological polar surface area82.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.