Piperacillin
Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class. The chemical structure of piperacillin and other ureidopenicillins incorporates a polar side chain that enhances penetration into Gram-negative bacteria and reduces susceptibility to cleavage by Gram-negative beta lactamase enzymes. These properties confer activity against the important hospital pathogen Pseudomonas aeruginosa. Thus piperacillin is sometimes referred to as an "anti-pseudomonal penicillin".
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Trade names | Pipracil |
AHFS/Drugs.com | Consumer Drug Information |
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Routes of administration | Intravenous (IV), intramuscular (IM) |
Drug class | β-lactam antibiotic |
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Bioavailability | 0% oral |
Protein binding | 30% |
Metabolism | Largely not metabolized |
Elimination half-life | 36–72 minutes |
Excretion | 20% in bile, 80% unchanged in urine |
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ECHA InfoCard | 100.057.083 |
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Formula | C23H27N5O7S |
Molar mass | 517.56 g·mol−1 |
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When used alone, piperacillin lacks strong activity against the Gram-positive pathogens such as Staphylococcus aureus, as the beta-lactam ring is hydrolyzed by the bacteria's beta-lactamase.
It was patented in 1974 and approved for medical use in 1981. Piperacillin is most commonly used in combination with the beta-lactamase inhibitor tazobactam (piperacillin/tazobactam), which enhances piperacillin's effectiveness by inhibiting many beta lactamases to which it is susceptible. However, the co-administration of tazobactam does not confer activity against MRSA, as penicillin (and most other beta lactams) do not avidly bind to the penicillin-binding proteins of this pathogen. The World Health Organization classifies piperacillin as critically important for human medicine.