Hetacillin

(CC) Image: David E. Volk
Hetacillin

Hetacillin is a penicillin-like, beta-lactam based antibiotic prodrug used to treat infections, usually from gram-positive bacteria.

Mechanism of action

Hetacillin is a prodrug with no antibacterial activity, but it is metabolized into the antibiotic ampicillin. Hetacillin is prepared by reacting ampicillin with acetone because ampicillin is much less stable towards ring-opening reactions. Once converted to ampicillin, the ampicillin interferes with the final stage of cell wall synthesis by binding to penicillin-binding proteins, leading to autolysis of the bacteria by autolysin enzymes.

Chemistry

It is a beta-lactam structure, and its chemical name is (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. Its chemical formula is C₁₉H₂₃N₃O₄S (MW = 389.4686 g/mol).

External links

• Hetacillin - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
• Drug Bank [1]