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Abstract

SYNTHESIS AND PHYSICOCHEMICAL CHARACTERIZATION OF CEFDINIR PRODRUGS

Shetul Patel*, Vinod Mandowara, Dipak Gupta, Punit Parejiya, Dharmik Mehta, Hetal Patel and Pragna Shelat

ABSTRACT

Cefdinir is one of the third generation cephalosporin which has broad spectrum antibacterial activity. Cefdinir has activity against Grampositive and Gram-negative bacteria. It is also effective against β- lactamase producing strains of haemophilis and neisseria. This drug is used to treat wide variety of sensitive bacterial infections, especially for mild and moderate infections disorders. The success of cefdinir is limited due to poor permeability of drug across cell membrane. Prodrug is one of the strategies to reduce the required dose of the drugs in order to achieve the desired bioavailability with enhanced permeability. In the present study, three different prodrugs of cefdinir (cefdinir methyl ester (CEF-1), cefdinir ethyl ester (CEF-2) and cefdinir benzyl ester (CEF-3) were synthesized. Further they were evaluated for physicochemical properties including solubility and partition coefficient. Ester prodrugs were found to be more soluble at pH 1.2 whereas cefdinir was found to have solubility at pH 1.2 and pH 7.4 due to amphoteric nature. Both drug as well as prodrugs was found to be stable at pH 1.2 as compared to pH 7.4. Additionally introduction of ester group in cefdinir increased the lipophilicity as observed in partition coefficient study. Prodrugs were found to be more lipophilic than cefdinir and were found to be interesting for further in-vivo animal study.

Keywords: lipophilicity, haemophilis and Neisseria.


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