Hetacillin: Difference between revisions

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== External links ==
== External links ==
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* Drug Bank [http://www.drugbank.ca/cgi-bin/getCard.cgi?CARD=DB00739.txt]
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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).

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