Ataluren

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

What is the Ataluren?

The molecule Ataluren presents a molecular formula of C15H9FN2O3 and its IUPAC name is 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid.

Ataluren (trade name: Translarna) is a small molecule drug that is used to treat patients with a specific type of genetic disorder called nonsense mutation Duchenne muscular dystrophy (nmDMD). Nonsense mutations are a type of genetic mutation that cause the synthesis of abnormal, shortened proteins that do not function properly. NmDMD is a severe and progressive muscle-wasting disease that affects boys and is caused by nonsense mutations in the dystrophin gene..

Ataluren works by inhibiting the premature termination of protein synthesis that is caused by nonsense mutations. By allowing the synthesis of full-length proteins, Ataluren may help to improve muscle function and slow the progression of nmDMD..

Ataluren has been evaluated in several clinical trials and has been shown to improve muscle function in patients with nmDMD. However, the overall clinical benefit of Ataluren in nmDMD is modest and it is not a cure for the disease. In addition, Ataluren is not effective in treating all types of DMD and it is not recommended for use in patients with other types of genetic disorders..

Ataluren is typically administered orally and is available as a tablet. The most common side effects of Ataluren include stomach pain, diarrhea, and weight loss. More serious side effects, such as allergic reactions, have also been reported..

Summary

From all the above, this molecule is a small molecule drug that is used to treat patients with nonsense mutation Duchenne muscular dystrophy (nmDMD). It works by inhibiting the premature termination of protein synthesis caused by nonsense mutations and may help to improve muscle function in nmDMD patients. However, Ataluren is not a cure for the disease and it is not effective in treating all types of DMD. It is typically administered orally and is available as a tablet, with common side effects including stomach pain, diarrhea, and weight loss..

3D structure

Cartesian coordinates

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

2D drawing

 

Ataluren OOUGLTULBSNHNF-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Ataluren

 

Molecule descriptors

 
IUPAC name3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
InChI codeInChI=1S/C15H9FN2O3/c16-12-7-2-1-6-11(12)14-17-13(18-21-14)9-4-3-5-10(8-9)15(19)20/h1-8H,(H,19,20)
InChI KeyOOUGLTULBSNHNF-UHFFFAOYSA-N
SMILESO=C(O)c1cccc(-c2noc(-c3ccccc3F)n2)c1

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.

  • 3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzoic acid
  • 3-[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid
  • 3-[5-(2-Fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
  • 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]benzoic acid
  • 304F579
  • 775304-57-9
  • AC-28390
  • AM808091
  • AU-004/43508117
  • Ataluren
  • Ataluren (PTC124)
  • Ataluren (USAN/INN)
  • Ataluren(ptc124)
  • Ataluren; PTC124
  • BB 0261439
  • BBL102158
  • BCP01756
  • BCPP000097
  • Benzoic acid, 3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)-
  • Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-
  • CCG-267286
  • CS-0503
  • D09323
  • DB05016
  • DSSTox_CID_26776
  • DSSTox_GSID_46776
  • DSSTox_RID_81895
  • EC-000.2051
  • EX-3387
  • EX-A385
  • FT-0651455
  • GS-3946
  • GTPL7341
  • HMS3656H20
  • HY-14832
  • JBF
  • K16AME9I3V
  • MFCD09864996
  • MLS006011160
  • NCGC00168759
  • NCGC00168759-02
  • NCGC00168759-04
  • NCGC00168759-05
  • NCGC00168759-10
  • PTC 124
  • PTC-124
  • PTC124
  • PTC124 (Ataluren)
  • PTC124 - Ataluren
  • PTC124,Ataluren
  • PTC124;3-[5-(2-Fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid;PTC-124
  • Q753330
  • SB16685
  • SMR004702931
  • STL555957
  • SW219696-1
  • Translarna
  • s6003

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13831791
  • CAS-775304-57-9
  • UNII-K16AME9I3V
  • AKOS005146455
  • ALBB-036381
  • BRD-K94830329-001-01-4
  • DTXSID5046776
  • CHEMBL256997
  • CHEBI:94805
  • Tox21_112631
  • Tox21_112631_1
  • SCHEMBL60614

Physico-Chemical properties

IUPAC name3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
Molecular formulaC15H9FN2O3
Molecular weight284.242
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity72.09
LogP3.2
Topological polar surface area76.2

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.