Orlistat

Orlistat is a synthetic bicyclic lactone containing a tetrahydronaphthalene ring system substituted with a chiral cyclohexane-derived side chain bearing multiple stereocenters and diol functionalities. Its core structure features an ester-linked carbamate moiety critical for lipase inhibition via covalent enzyme binding. The compound exhibits three adjacent hydroxyl groups in a 1,2,3-triol configuration, contributing to conformational rigidity. As the parent drug's active pharmaceutical ingredient, it is synthesized via stereoselective alkylation of naphthalene derivatives followed by macrolactonization. This compound serves as an HPLC reference standard for pharmaceutical quality control.