Amoxicillin Inactivation by Thiol-Catalyzed Cyclization Reduces Protein Haptenation and Antibacterial Potency

What is it about?

The antibiotic amoxicillin looses its ability to stop bacterial growth in the presence of compounds that bear a thiol group (-SH). This effect is due to the conversion of amoxicillin into a diketopiperazine metabolite.

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Why is it important?

Because amoxicillin is administered in combination with N-acetyl-cysteine, a mucolytic agent bearing a thiol group, in many opportunities. Moreover, amoxicillin will encounter many thiol bearing compouns, including serum proteins, which may inactivate the antibiotic or become modified by amoxicillin. In the latter case, creating epitopes that can contribute to allergic reactions.