Piperacillin

Piperacillin
ATC Code J01CA12
Formula C23H27N5O7S
Molar Mass (g·mol−1) 517,56
Physical State solid
Melting Point (°C) 183–185
CAS Number 61477-96-1
PUB Number 43672
Drugbank ID DB00319
Solubility sparingly soluble in water

Basics

Piperacillin is a broad-spectrum β-lactam antibiotic in the ureidopenicillin class. The chemical structure of piperacillin and other ureidopenicillins contains a polar side chain that increases 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. Therefore, piperacillin is sometimes referred to as "anti-Pseudomonas penicillin". Piperacillin is used almost exclusively in combination with the beta-lactamase inhibitor tazobactam to treat serious hospital-acquired infections.

Pharmacology

Pharmacodynamics

By binding to specific penicillin-binding proteins (PBPs) located within the bacterial cell wall, piperacillin inhibits the third and final stage of bacterial cell wall synthesis. Cell lysis (dissolution of the cell) is then mediated by bacterial cell wall enzymes, also called autolysins. This stops bacterial proliferation and destroys the pathogen.

Pharmacokinetics

Piperacillin is not orally absorbed and therefore must be administered by intravenous or intramuscular injection. It is largely unmetabolized and excreted unchanged by the kidneys. The half-life is between 30 and 70 minutes.

Drug Interactions

Some compounds that may interfere with the bactericidal activity of piperacillin are chloramphenicol, macrolides, and sulfonamides.

Toxicity

Side effects

Common side effects associated with the administration of piperacillin-tazobactam include:

  • Gastrointestinal: constipation, diarrhea, nausea, vomiting.
  • Dermatological: erythema, pain, phlebitis, rash
  • Neurological: headache, insomnia

Prolonged piperacillin-tazobactam therapy has been associated with the possible development of hematologic adverse reactions such as leukopenia (16.3%), neutropenia (10%), and eosinophilia (10%) in adult patients.

Toxicological Data

LD50 (rat, oral): > 10 g-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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