Fezolinetant, the first-in-class hot flashes drug, was flagged in September 2024 by US-FDA for liver injury. It is alarming that an FDA-approved drug shows liver toxicity within a year. Fezolinetant's metabolic pathways and metabolites are not disclosed in the FDA label, clinical trial, or other literature reports. This creates a gap in understanding the mechanisms of metabolism and toxicity. In this manuscript, we have investigated novel metabolic pathways that generate reactive metabolites and rationalize hepatotoxicity. Quantum chemical calculations were performed to assess the reactivity of various sites using B3LYP/CC-PVTZ level of theory and H