Piperacillin
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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 | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a694003 |
| Pregnancy cat. | B |
| Legal status | POM (UK) |
| Routes | IV, IM |
| Pharmacokinetic data | |
| Bioavailability | not absorbed orally |
| Metabolism | largely not metabolised |
| Half-life | 36–72 minutes |
| Excretion | 20% in bile, 80% unchanged in urine |
| Identifiers | |
| CAS number | 61477-96-1  |
| ATC code | J01CA12 |
| PubChem | CID 43672 |
| IUPHAR ligand | 422 |
| DrugBank | APRD00325 |
| ChemSpider | 39798 |
| UNII | 9I628532GX |
| KEGG | D08380 |
| ChEBI | CHEBI:8232 |
| ChEMBL | CHEMBL702 |
| Chemical data | |
| Formula | C23H27N5O7S |
| Mol. mass | 517.555 g/mol |
| SMILES | eMolecules & PubChem |
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Piperacillin is an extended spectrum beta-lactam antibiotic of the ureidopenicillin class.
It is normally used together with a beta-lactamase inhibitor such as tazobactam. The combination drug piperacillin/tazobactam is commercially available as e.g. Tazocin, Zosyn, Brodactam, Piptaz and as Trezora. The combination has activity against many Gram-positive and Gram-negative pathogens and anaerobes, including Pseudomonas aeruginosa.
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[edit] Administration
Piperacillin is not absorbed orally, and must therefore be given by intravenous or intramuscular injection; piperacillin/tazobactam is administered intravenously every 6 or 8 hours; the drug may also be given by continuous infusion. 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]
[edit] Uses
Its main uses are in intensive care medicine (pneumonia, peritonitis), some diabetes-related foot infections and empirical therapy in febrile neutropenia (e.g., after chemotherapy).
[edit] Trade names and preparations
Piperacillin alone:
- Piperacillin (U.S., marketed by Istituto Biochimico)
Piperacillin/tazobactam:
- Tazocin (UK, marketed by Wyeth)
- Tazocin (New Zealand, marketed by Wyeth)
- Zosyn (U.S., marketed by Wyeth)
[edit] References
- ^ 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 1635208. PMID 16940077. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1635208.
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[edit] External links
- Zosyn (piperacillin/tazobactam combination) - information for U.S.
- Tazocin data sheet for New Zealand
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