Piperacillin
| Clinical data | |
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| Trade names | Pipracil | 
| AHFS/Drugs.com | Consumer Drug Information | 
| Pregnancy category | 
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| Routes of administration | Intravenous (IV), intramuscular (IM) | 
| Drug class | β-lactam antibiotic | 
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| Pharmacokinetic data | |
| 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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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.057.083 | 
| Chemical and physical data | |
| Formula | C23H27N5O7S | 
| Molar mass | 517.56 g·mol−1 | 
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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".
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.