Parecoxib meta isomer is a positional isomer of the parent NSAID prodrug parecoxib, characterized by a meta-substituted aryl sulfonamide moiety relative to the pyrazole ring. Its structure incorporates a 4-pyridyl ester linked to a meta-oriented phenylsulfonamide group, differing from the para configuration in the parent compound. The molecule retains the core 2-propylpyrazole framework but exhibits altered steric and electronic properties due to the meta substitution. This isomer arises as a synthetic byproduct during API manufacturing via divergent sulfonamide coupling pathways. It serves as an HPLC reference standard for impurity profiling in parecoxib formulations.
On RequestCCC(=O)NS(=O)(=O)C1=CC=CC(=C1)C2=C(ON=C2C3=CC=CC=C3)C
InChI=1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-7-10-15(12-16)18-13(2)25-20-19(18)14-8-5-4-6-9-14/h4-12H,3H2,1-2H3,(H,21,22)
LBJQZHNREKXOHS-UHFFFAOYSA-N