3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid

• ChemBase ID: 73078
• Molecular Formular: C15H9FN2O3
• Molecular Mass: 284.2419632
• Monoisotopic Mass: 284.05972038
• SMILES: c1c(cccc1C(=O)O)c1noc(n1)c1ccccc1F
• Canonical SMILES: Fc1ccccc1c1onc(n1)c1cccc(c1)C(=O)O
• InChI: InChI=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)
• InChIKey: OOUGLTULBSNHNF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
• IUPAC Traditional name: ataluren
• Synonyms: Ataluren; PTC124; 3-(5-(2-Fluorophenyl)-1,2,4-oxadiazol-3-yl)benzoic acid; Ataluren

Database IDs

• CAS Number: 775304-57-9
• PubChem SID: 162037998
• PubChem CID: 11219835
• CHEMBL: 256997
• Chemspider ID: 9394889
• KEGG ID: D09323
• Wikipedia Title: Ataluren

CALCULATED PROPERTIES

• Acid pKa: 3.9006183
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.3136253
• LogD (pH = 7.4): 0.6775237
• Log P: 3.9193923
• Molar Refractivity: 94.6594 cm^3
• Polarizability: 28.013302 Å^3
• Polar Surface Area: 76.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 95+%; 97%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S6003

Research Area

• Description: Inflammation

Protocol

• Protocol: Kinase Assay ^[1]
• Assays for read-through of LUC premature termination codons: Stock solutions of PTC124 (6 mM) are prepared in 100% DMSO HEK293 cells grown in a medium containing fetal bovine serum (FBS) and are stably transfected with LUC genes containing premature terminators at codon 190 (and 11 contextual variants thereof), treated with increasing concentrations of PTC124 for 16 hours, and assayed for luciferase activity. Luminescence of each culture relative to the control is quantified by standard procedures using a Viewlux CCD imager. Luminescence data are normalized to that produced with DMSO, and the fold suppression over background is calculated as (PTC124_{light units}/DMSO_{light units}).
• Protocol: Animal Study ^[2]
• Animal Models: Cftr-/- hCFTR-G542X transgenic mice
• Formulation: Dissolved in DMSO, and diluted in saline
• Doses: ~60 mg/kg/day
• Administration: Subcutaneous injection or oral administration

References

• References: [1] Welch EM, et al. Nature, 2007, 447(7140), 87-91.
• References: [2] Du M, et al. Proc Natl Acad Sci U S A, 2008, 105(6), 2064-2069.

REFERENCES

• Welch EM, et al. Nature, 2007, 447(7140), 87-91.
• Du M, et al. Proc Natl Acad Sci U S A, 2008, 105(6), 2064-2069.