Piperacillin

Piperacillin

File:Piperacillin.svg
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
Pregnancy category	B
Routes of administration	IV, IM
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	not absorbed orally
Metabolism	largely not metabolised
Biological half-life	36–72 minutes
Excretion	20% in bile, 80% unchanged in urine
Identifiers
CAS Number	61477-96-1
ATC code	J01CA12 (WHO)
PubChem	CID 43672
IUPHAR/BPS	422
DrugBank	APRD00325
Chemical data
Formula	C23H27N5O7S
Molar mass	517.555 g/mol[[]]
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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 of piperacillin and tazobactam is commercially available as e.g. Tazocin, Zosyn or Brodactam and as TREZORA . The combination has activity against many Gram-positive and Gram-negative pathogens and anaerobes, including Pseudomonas aeruginosa.

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.

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).

Trade names and preparations

Piperacillin alone:

• Pipracil (U.S. only)

Piperacillin/tazobactam:

• Tazocin (UK, marketed by Wyeth)
• Tazocin (Japan, marketed by Toyama)
• Tazocin (New Zealand, marketed by Wyeth)
• Zosyn (U.S., marketed by Wyeth)
• Brodactam (marketed by sanofi-aventis)
• TREZORA (India, Marketed by Nucleus)

External links

• Zosyn (piperacillin/tazobactam combination) - information for U.S.
• Tazocin data sheet for New Zealand

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