In the present work our goal was to explore the prodrug approach study especially for colon targeting antibacterial agents. We choose the sulfonamides as an antibacterial agent for colon targeting treatments. For this purpose sulfonamides were coupled to carvacrol through azo compound formation. The newly synthesized azo compounds were characterized by spectral techniques such as Infrared (IR), Proton Nuclear Magnetic Resonance (1H-NMR) and Carbon-13 Nuclear Magnetic Resonance (13C-NMR). The drug released study of the parent compound was done by in vitro enzyme degradation by using azoreductase enzyme which was secreted by pseudomonas aeruginosa bacterium. Carvacrol and its derivatives were known show remarkable biological activity such as antimicrobial, antitumor, antimutagenic, antigenotoxic, analgesic, antispasmodic, anti-inflammatory, angiogenic, antiparasitic, antiplatelet, Ache inhibitory, antielastase, insecticidal, antihepatotoxic and hepatoprotective activities. However sulfonamides were also the most effective agent against most of the bacteria. The parent drug release was confirmed by the new spectral technique HPTLC. The combine formulation of sulfonamide and carvacrol as azo compounds gives the new tool for colon targeting agents as well as for urinary tract disorders, and they can also find new varieties of applications in the field of medicinal and pharmaceutical chemistry.