Piperacillin

Piperacillin
Clinical data
Trade namesPipracil
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous (IV), intramuscular (IM)
Drug classβ-lactam antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability0% oral
Protein binding30%
MetabolismLargely not metabolized
Elimination half-life36–72 minutes
Excretion20% in bile, 80% unchanged in urine
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.057.083 Edit this at Wikidata
Chemical and physical data
FormulaC23H27N5O7S
Molar mass517.56 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)C(=O)N(CC)CC2)[C@H]4SC3(C)C
  • InChI=1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1 checkY
  • Key:IVBHGBMCVLDMKU-GXNBUGAJSA-N checkY
  (verify)

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]

It was patented in 1974 and approved for medical use in 1981.[3] 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.[4] The World Health Organization classifies piperacillin as critically important for human medicine.[5]

  1. ^ Tan JS, File TM (July 1995). "Antipseudomonal penicillins". The Medical Clinics of North America. 79 (4): 679–93. doi:10.1016/s0025-7125(16)30032-3. PMID 7791416.
  2. ^ Hauser, AR Antibiotic Basics for Clinicians, 2nd Ed., Wolters Kluwer, 2013, pg 26-27
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 491. ISBN 9783527607495.
  4. ^ Zhanel GG, DeCorby M, Laing N, Weshnoweski B, Vashisht R, Tailor F, et al. (April 2008). "Antimicrobial-resistant pathogens in intensive care units in Canada: results of the Canadian National Intensive Care Unit (CAN-ICU) study, 2005-2006". Antimicrobial Agents and Chemotherapy. 52 (4): 1430–7. doi:10.1128/AAC.01538-07. PMC 2292546. PMID 18285482.
  5. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.