Metabolism of phenacetin (N-4-Ethoxyphenyl) ethanamide) in human body



In the human body, phenacetin is metabolized into two compounds, a minor (hydroxamic acid) product and a major product (paracetamol). One of the processes encompasses the replacing ethyl group (CH3CH2-) with a hydrogen atom (H) at carbon number four.

The other process involves removal of hydrogen from a nitrogen atom and then replacing it with a hydroxyl group (OH-). The first process results in the formation of paracetamol while the second process leads to the formation of hydroxamic acid. It is believed that hydroxamic acid contributes to the toxicity of phenacetin since it binds strongly to metal ions. The following figure shows what takes place during the phenacetin metabolism process.

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