Synthesis, Characterization, and Docking Studies of 1,4-dien as a Potential Impurity in Bimatoprost Drug.

INTRODUCTION

The origin, synthesis, characterization and docking studies of (Z)-7- ((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,1E,4E)-3-hydroxy-5-phenylpenta-1,4-dien-1- yl)cyclopentyl)-N-ethylhept-5-enamide, an impurity generated in the preparation of an antiglaucoma agent-Bimatoprost has been described.

METHODS

This impurity was controlled by employing 30% Pd/C, and the impurity level was brought to the permissible level, i.e., 0.03% (ICH guidelines) in the final drug preparation of Bimatoprost.

RESULTS

Finally, induced-fit docking calculations were performed to theoretically evaluate the binding efficiencies of these inhibitors in the crystal structure of Prostaglandin F synthase (PGFS).

CONCLUSION

There are negligible differences in RMSD and docking scores between the two ligands, which amount to only 0.18 Å and 0.313 kcal/mol, respectively. These findings strongly indicate that both ligands are likely to exhibit similar biological functions and efficiencies.