As a preface to this research, it was important to look at the challenges facing industry during new product development. There was an attempted to familiarize this research with current directives and maintain product driven research, via pharmaceutical development by re-engineering an effective product/s. Per this directive, the research herein was directed toward improving the biopharmaceutical properties of an effective osteoarthritis therapy, glucosamine. Initially our studies were focused on transdermally delivering glucosamine to improve its bioavailability, leading to how a delivery method can influence a chemical entitys biopharmaceutical properties. These studies failed early on and later succeeded. Another prospective of drug delivery arose from the synthesis of mutual prodrugs based on a NSAID (non-steroidal anti-inflammatory drug) and a glucosamine molecule covalently bound via an ester linkage(s) to modify each active chemical entitys biopharmaceutical properties. The first project was geared towards the transdermal/percutaneous delivery of glucosamine, a nutraceutical used to treat osteoarthritis (OA). Published, unpublished and our studies have shown that the orally administered glucosamine salts, its parent molecule or highly recognized metabolite chondroitin cannot be transdermally/percutaneously delivered via traditional means. These studies were completed with via the transdermal delivery of a glucosamine metabolite, N-acetyl-D-glucosamine (NAG). These studies investigated the permeability of NAG in various permeation enhancer suspensions and simple pluronic-organo gel formulations utilizing shed snakeskin as a model membrane via Franz-type cell diffusion studies. Findings show NAG to be an excellent candidate for the transdermal transport of glucosamine. The synthesis of NSAID-glucosamine derivative mutual prodrugs has been an attempt to improve the biopharmaceutical properties of the parent compounds such as permeability, solubility and stability. These chemical entities were produced as models towards the delivery of glucosamine and NSAIDs as concomitant agents that halt the progress of OA and produce known anti-inflammatory effects respectively. The synthesized compounds were characterized and evaluated in silico to predict the biopharmaceutical properties. Initial predictive findings show these products to be mutual prodrug candidates to concomitantly deliver synergistic OA therapies.