1st Day of Organic Chemistry and its Medicinal and Industrial Applications

Detection of Chiral Impurity of S-Naproxen Using Vancomycin Chiral Selector

Non programmé

20m

Auditorium Mouloud Kacem Nait BELKACEM (Setif1- University Ferhat ABBAS)

Orateurs

Dr Dehbiya GHERDAOUI (Laboratory of Biomaterials and Transport Phenomena (LBMPT), New Urban Pole, Medea University, Medea 26000, Algeria)Dr Fatma BOUAZZADr samira IHADADENE (Laboratoire d’Analyse Organique Fonctionnelle, Faculté de Chimie, USTHB, B.P. 32, El Alia, Bab Ezzouar 16111, Alger, Algeria)

Description

Abstract
Naproxen (NAP) is a non-steroidal anti-inflammatory drug (NSAID) of the arylacetic acid group, Naproxen is used to relieve the pain, inflammation and stiffness. Enantiomeric purity of naproxen is important, as the R- isomer is hepatotoxic while the S- isomer is safe. Also, the S- isomer of the drug has 28 times than the anti-inflammatory activity of the R- isomer. The use of an amino column as the stationary phase and of a mobile phase consisting of propanol/phosphate buffer (pH 6.0, 0.05 M) (50:50, v/v) with vancomycin as a chiral selector was found to be optimal for identifying the enantiomeric impurities of S-naproxen. This result was attributed to the establishment of various interactions between vancomycin and naproxen, such as hydrogen bonding, electrostatic and Van der Waals interactions . The testing of the chiral purity of S-naproxen under these chromatographic conditions resulted in a good selectivity of 2.15 and a high resolution of 2.5. Similar results were obtained in the optical purity test of S-naproxen using vancomycin as a chiral column, while no previous studies using vancomycin as a CMPA are available .
Key words: Stereo-chemistry; Chiral impurity, Naproxen, Chiral selector.