Title:Synthesis, Characterization and Antimicrobial Evaluation of Lipid Based Norfloxacin Prodrug
Volume: 15
Issue: 2
Author(s): Prabodh Chander Sharma*, Mona Piplani and Harish Rajak
Affiliation:
- Institute of Pharmaceutical Sciences, Kurukshetra University, Kurukshetra-136119,India
Keywords:
Antibacterial, bioavailability, drug release, fatty acid, partition coefficient, prodrug.
Abstract: Background: Fluoroquinolones, the synthetic antibacterial agents are being successfully utilized
against bacterial infections, since the time immemorial. Despite of enormous useful features, these
drugs are associated with some limitations also. Large number of efforts has been made by various scientists
to improve pharmacokinetic properties of these drugs and hence, to overcome the limitations associated
with them.
Objectives: The aim of this paper is to introduce a novel scheme for synthesis of prodrug with improved
pharmacokinetic properties i.e., lipophilicity and consequently, modified bioavailability of norfloxacin.
Methods: Fatty acid hydrazide of selected fatty acid was synthesized followed by preparation of
5-formyl salicylamide. N-Mannich base of norfloxacin was synthesized by reacting norfloxacin with
5-formyl salicylamide. The prodrug was obtained by covalently coupling this N-Mannich base of norfloxacin
with fatty acid hydrazide. The synthesized lipid based prodrug was evaluated for partition coefficient
by shake flask method and screened for antimicrobial activity against selected strains. Drug content
determination and in vitro dissolution studies utilizing HPLC were also carried out.
Results: The synthesized prodrug was found to exhibit improved partition coefficient (1.15) when compared
with parent drug, norfloxacin (0.46). The results of antimicrobial evaluation indicate promising
antibacterial and antifungal activity.
Conclusion: The synthesized prodrug proved to be a good antimicrobial substance due to improved
lipophilicity and would be expected to be used as a suitable candidate for exploration of possible utilities
in treatment of bacterial infections in forthcoming time.
