(S)-aminoglutethimide

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

What is the (S)-aminoglutethimide?

The molecule (S)-aminoglutethimide presents a molecular formula of C13H16N2O2 and its IUPAC name is (3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione.

S-Aminoglutethimide (AG) is a synthetic, non-steroidal drug that was first introduced in 1948 as an anticonvulsant. It is also used as an adjuvant in the treatment of breast cancer and has been investigated for other uses. The mechanism of action of AG is not fully understood, but it is thought to work by inhibiting the production of adrenal hormones, including cortisol..

AG is well absorbed from the gastrointestinal tract and is metabolized in the liver. The metabolites of AG are excreted in the urine. AG is a white, crystalline powder that is insoluble in water..

The most common side effects of AG are nausea, vomiting, and loss of appetite. Other side effects include dizziness, headache, drowsiness, and skin rash. AG can also cause a decrease in the production of adrenal hormones, which can lead to adrenal insufficiency. AG should be used with caution in patients with liver disease or kidney disease..

AG is a schedule II controlled substance in the United States and exists by prescription only..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-aminoglutethimide ROBVIMPUHSLWNV-ZDUSSCGKSA-N chemical compound 2D structure molecule svg
(S)-aminoglutethimide

 

Molecule descriptors

 
IUPAC name(3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
InChI codeInChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)/t13-/m0/s1
InChI KeyROBVIMPUHSLWNV-ZDUSSCGKSA-N
SMILESCC[C@@]1(c2ccc(N)cc2)CCC(=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.

  • (-)-(S)-Aminoglutethimide
  • (-)-Aminoglutethimide
  • (3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
  • (S)-(-)-Aminoglutethimide
  • (S)-aminoglutethimide
  • 2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-, (3S)-
  • 57288-03-6
  • 5S1T2OED7F
  • Aminoglutethimide, (S)-
  • BDBM50406640
  • D-Aminoglutethimide
  • Lopac-A-9657
  • NCGC00015110-01
  • NCGC00016379-01
  • Q27124214

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1530855
  • CAS-125-84-8
  • UNII-5S1T2OED7F
  • CHEMBL1394757
  • CHEBI:53790
  • SCHEMBL116988

Physico-Chemical properties

IUPAC name(3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
Molecular formulaC13H16N2O2
Molecular weight232.278
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity69.54
LogP2.3
Topological polar surface area72.2

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.