This work aims to enhance the solubility of poorly water-soluble drug glyburide by using the synthesised dendrimer. The potential of dendritic macromolecules generation one, generation two and generation three (HG1.0, HG2.0 and HG3.0) as solubility enhancers of drugs were investigated by applying the Higuchi and Connors method. The effect of pH, concentration and generation of synthesised dendrimers on the solubility of Glyburide was studied. FT-IR, 1H NMR & Mass spectroscopy to explore and evaluate the structure of synthesised dendrimers. The results of the experiment suggested that Glyburide’s solubility was improved with increasing dendrimer concentration and dendrimer generation.