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Rafik Karaman*, Samia Al-Kurd, Reem Yaghmour, Ahmad Amro,
Donia Karaman


Two novel prodrugs of amoxicillin and cephalexin (amoxicillin ProD 1 and cephalexin ProD 1, respectively) were designed and synthesized to improve the stability and bitter sensation of their parent drugs. The in vitro susceptibility for both prodrugs was determined against Escherichia coli, staphylococcus epidermidis, staphylococcus aureus, Klebsiella pneumonia, streptococcus group A and streptococcus group B, and was compared to that of their active parent drugs.The antibacterial screening demonstrates that amoxicillin ProD 1 and cephalexin ProD 1 were found to be active and are considered among a small number of prodrugs that have therapeutic activity themselves before undergoing interconversion via enzymatic or chemical reaction to their corresponding active parent drugs. Both prodrugs exhibit their antibacterial activity against different types of bacterial strains due to the presence of β- lactam ring in their structures. In addition, it is expected that these novel prodrugs will be much more stable in aqueous media than their corresponding active parent drugs due to the fact that the chemically sensitive amine group contained in the active parent drug structures is replaced with an amide, more chemically stable group, in the corresponding prodrugs.

Keywords: Antibacterials, amoxicillin, cephalexin, prodrugs, bitter sensation, cleavage.

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