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Systematic (IUPAC) name
(2S,5R,6R)-6-{[(2R)-2-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)amino]-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names Pipracil
AHFS/Drugs.com Consumer Drug Information
  • B
Legal status
Routes IV, IM
Pharmacokinetic data
Bioavailability 0% oral
Protein binding Slightly less than Amoxicillin
Metabolism largely not metabolized
Half-life 36–72 minutes
Excretion 20% in bile, 80% unchanged in urine
CAS number 61477-96-1 YesY
ATC code J01CA12
PubChem CID 43672
IUPHAR ligand 422
DrugBank DB00319
ChemSpider 39798 YesY
UNII 9I628532GX YesY
KEGG D08380 YesY
Chemical data
Formula C23H27N5O7S 
Molecular mass 517.555 g/mol
 YesY (what is this?)  (verify)

Piperacillin is an extended-spectrum beta-lactam antibiotic of the ureidopenicillin class. It is normally used together with a beta-lactamase inhibitor, notably in the combination piperacillin/tazobactam.


Piperacillin is not absorbed orally, and must therefore be given by intravenous or intramuscular injection. It has been shown that the bacteriocidal actions of the drug do not increase with concentrations of piperacillin higher than 4-6xMIC, which means that the drug is concentration-independent in terms of its actions. Piperacillin has instead shown to offer higher bacteriocidal activity when its concentration remains above the MIC for longer periods of time (50% time>MIC showing the highest activity). This higher activity (present in continuous dosing) has not been directly linked to clinical outcomes, but however does show promise of lowering possibility of resistance and decreasing mortality.[1]