Levofloxacin, commonly used in medical practice, is prescribed to treat pneumonia in patients with comorbidities. Although generally well tolerated and safe, it has a well-known, but rarely reported, undercharacterized and ill-identified hepatotoxicity, with an unknown signature. With cases of fulminant hepatitis, cholestasis episodes reveal an apparently benign progression. Its capability of interference with the glucidic metabolism is also well-known, and the susceptibility factors to these events include age, presence of multiple pathologies and polymedication. The link between Diabetes Mellitus and hepatotoxicity has not yet been identified. Nonetheless, reports of several cases in literature along with the identification of two cases in insulin-treated diabetics, lead to believe that this is a higher-risk group.