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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
Routes of
Legal status
Legal status
Pharmacokinetic data
Bioavailability 0% oral
Protein binding 30%
Metabolism Largely not metabolized
Biological half-life 36–72 minutes
Excretion 20% in bile, 80% unchanged in urine
CAS Number 61477-96-1 YesY
ATC code J01CA12 (WHO)
PubChem CID 43672
DrugBank DB00319 YesY
ChemSpider 39798 YesY
UNII 9I628532GX YesY
KEGG D08380 YesY
Chemical data
Formula C23H27N5O7S
Molar mass 517.555 g/mol

Piperacillin is a broad-spectrum β-lactam antibiotic of the ureidopenicillin class.[1] 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.[2]

Piperacillin is most commonly used in combination with the beta-lactamase inhibitor tazobactam (Piperacillin/Tazobactam) (tradename "Zosyn" or "Tazocin"), which enhances piperacillin's effectiveness by inhibiting many beta lactamases to which it is susceptible. The co-administration of tazobactam does not confer activity against MRSA, however, as penicillins (and most other beta lactams) do not avidly bind to the penicillin-binding proteins of this pathogen.[3]

Medical uses[edit]

Piperacillin is used almost exclusively in combination with the beta lactamase inhibitor tazobactam for the treatment of serious, hospital-acquired infections. This combination is among the most widely used drug therapies in United States non-Federal hospitals, accounting for $388M in spending in spite of being a low-cost generic drug.[4]

Piperacillin-tazobactam is recommended as part of a three drug regimen for the treatment of hospital-acquired pneumonia suspected as being due to infection by multi-drug resistant pathogens.[5] It is also one of several antibacterials recommended for the treatment of infections known to be caused by anaerobic Gram negative rods.[6]

Piperacillin-tazobactam is recommended by the National Institute for Health and Care Excellence as initial empiric treatment for people with suspected neutropenic sepsis.[7]

Adverse effects[edit]

The most common adverse effects associated with piperacillin-tazobactam are diarrhea, constipation, nausea, headache and insomnia. Less commonly, severe adverse effects may include anaphylaxis, Stevens-Johnson syndrome, and Clostridium difficile associated diarrhea.[8]


Piperacillin is not absorbed orally, and must therefore be given by intravenous or intramuscular injection. It has been shown that the bactericidal actions of the drug do not increase with concentrations of piperacillin higher than 4-6 x MIC, which means that the drug is concentration-independent in terms of its actions. Piperacillin has instead shown to offer higher bactericidal 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.[9]


  1. ^ Tan JS, File TM (1995). "Antipseudomonal penicillins". Med. Clin. North Am. 79 (4): 679–93. PMID 7791416. 
  2. ^ Hauser, AR Antibiotic Basics for Clinicians, 2nd Ed., Wolters Kluwer, 2013, pg 26-27
  3. ^ Zhanel GG, DeCorby M, Laing N, Weshnoweski B, Vashisht R, Tailor F, Nichol KA, Wierzbowski A, Baudry PJ, Karlowsky JA, Lagacé-Wiens P, Walkty A, McCracken M, Mulvey MR, Johnson J, Hoban DJ (2008). "Antimicrobial-resistant pathogens in intensive care units in Canada: results of the Canadian National Intensive Care Unit (CAN-ICU) study, 2005-2006". Antimicrob. Agents Chemother. 52 (4): 1430–7. doi:10.1128/AAC.01538-07. PMC 2292546free to read. PMID 18285482. 
  4. ^ Schumock GT, Li EC, Suda KJ, Wiest MD, Stubbings J, Matusiak LM, Hunkler RJ, Vermeulen LC (2015). "National trends in prescription drug expenditures and projections for 2015". Am J Health Syst Pharm. 72 (9): 717–36. doi:10.2146/ajhp140849. PMID 25873620. 
  5. ^ Mandell LA, Wunderink R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 257, pp 2139-2141
  6. ^ Kasper DL, Cohen-Poradosu R, in Harrison's Principles of Internal Medicine 18th Ed., Chapter 164, pp 1331-1339
  7. ^ "Neutropenic Sepsis: Prevention and Management of Neutropenic Sepsis in Cancer Patients - PubMed - NCBI". 
  8. ^ "Higlights of Prescribing Information - Zosyn (Piperacillin/Tazobactam)" (PDF). 
  9. ^ Lau W, Mercer D, Itani K, et al. (2006). "Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection". Antimicrob Agents Chemother. 50 (11): 3556–61. doi:10.1128/AAC.00329-06. PMC 1635208free to read. PMID 16940077.