(-)-Ethotoin

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

What is the (-)-Ethotoin?

The molecule (-)-Ethotoin presents a molecular formula of C11H12N2O2 and its IUPAC name is (5R)-3-ethyl-5-phenylimidazolidine-2,4-dione.

-Ethotoin (also known as fosphenytoin or CGP-39551) is a hydantoin anticonvulsant. It is structurally and functionally similar to phenytoin, but has a greater anticonvulsant effect and fewer side effects..

-Ethotoin is used to treat seizures and epilepsy. It is thought to work by stabilizing electrical activity in the brain..

-Ethotoin exists as an injection or as a tablet. It is typically taken two or three times a day..

-Common side effects of ethotoin include dizziness, drowsiness, and nausea..

-Ethotoin is a pregnancy category C drug, which means it may be harmful to a developing fetus. Women who are pregnant or planning to become pregnant should talk to their doctor before taking ethotoin..

3D structure

Cartesian coordinates

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

2D drawing

 

(-)-Ethotoin SZQIFWWUIBRPBZ-SECBINFHSA-N chemical compound 2D structure molecule svg
(-)-Ethotoin

 

Molecule descriptors

 
IUPAC name(5R)-3-ethyl-5-phenylimidazolidine-2,4-dione
InChI codeInChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)/t9-/m1/s1
InChI KeySZQIFWWUIBRPBZ-SECBINFHSA-N
SMILESCCN1C(=O)N[C@H](c2ccccc2)C1=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.

  • (-)-Ethotoin
  • (-)-ethotoin
  • (5R)-3-ethyl-5-phenylhydantoin
  • (5R)-3-ethyl-5-phenylimidazolidine-2,4-dione
  • (R)-(-)-ethotoin
  • (R)-Ethotoin
  • 2,4-Imidazolidinedione, 3-ethyl-5-phenyl-, (5R)-
  • 41807-37-8
  • 6026V958QL
  • BIDD:PXR0124
  • Ethotoin, (R)-
  • Q27127212

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC271
  • UNII-6026V958QL
  • DTXSID60487217
  • CHEBI:60359

Physico-Chemical properties

IUPAC name(5R)-3-ethyl-5-phenylimidazolidine-2,4-dione
Molecular formulaC11H12N2O2
Molecular weight204.225
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity62.84
LogP1.6
Topological polar surface area49.4

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.