(R)-Ethosuximide

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

What is the (R)-Ethosuximide?

The molecule (R)-Ethosuximide presents a molecular formula of C7H11NO2 and its IUPAC name is (3R)-3-ethyl-3-methylpyrrolidine-2,5-dione.

(R)-Ethosuximide is a molecule used as an anticonvulsant drug. It was first synthesized in 1952 and approved for use in the United States in 1959. Ethosuximide is used primarily to treat absence seizures, although it is also sometimes used to treat other types of seizures such as myoclonic seizures. The precise mechanism of action of ethosuximide is not known, but it is thought to work by inhibiting the action of a neurotransmitter called T-type calcium channels..

Ethosuximide is generally well-tolerated, with the most common side effects being nausea, vomiting, and dizziness. Rarely, more serious side effects such as Stevens-Johnson syndrome or blood disorders can occur. Ethosuximide should be used with caution in people with kidney or liver disease, as well as in pregnant or breastfeeding women..

If you or someone you know has epilepsy and is considering taking ethosuximide, be sure to talk to your doctor about the potential risks and benefits of this medication..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Ethosuximide HAPOVYFOVVWLRS-SSDOTTSWSA-N chemical compound 2D structure molecule svg
(R)-Ethosuximide

 

Molecule descriptors

 
IUPAC name(3R)-3-ethyl-3-methylpyrrolidine-2,5-dione
InChI codeInChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)/t7-/m1/s1
InChI KeyHAPOVYFOVVWLRS-SSDOTTSWSA-N
SMILESCC[C@]1(C)CC(=O)NC1=O

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.

  • (-)-ethosuximide
  • (3R)-3-ethyl-3-methylpyrrolidine-2,5-dione
  • (?)-Ethosuximide
  • (R)-(-)-ethosuximide
  • (R)-2-methyl-2-ethylsuccinimide
  • (R)-ETHOSUXIMIDE
  • (R)-Ethosuximide
  • 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-, (3R)-
  • 39122-20-8
  • Ethosuximide, (R)-
  • HYW082GZII
  • Lopac-E-7138
  • NCGC00015418-01
  • NCGC00016320-01
  • Q27127208

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530806
  • CAS-77-67-8
  • UNII-HYW082GZII
  • AKOS006273446
  • CHEMBL1489918
  • CHEBI:60354
  • SCHEMBL20980115

Physico-Chemical properties

IUPAC name(3R)-3-ethyl-3-methylpyrrolidine-2,5-dione
Molecular formulaC7H11NO2
Molecular weight141.168
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity40.51
LogP0.8
Topological polar surface area46.2

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.