Skin is the largest organ of the body with a surface area of about 2 square metres. It is best suitable when the site of medication is local and route of administration for systemic delivery. The skin permeability of most of the drugs is low, but can be enhanced using several technologies. The aim of this study was to design and synthesize novel cationic ester NSAI prodrugs possessing a permanent positive charge and appropriate physicochemical properties optimised for transdermal administration by anodal Iontophoresis. This multidisciplinary work provides new findings to the domain of skin drug delivery using iontophoresis technology for cationic therapeutical molecules. The sole presence of a permanent positive charge doesn't guarantee the success of the iontophoretic delivery of the cationic ester prodrug through skin but the availability of this charge for the electrical current interaction is crucial for the success of the electrically assisted method.