Substance

ID:204

Names and Identifiers
IUPAC name
sodium (2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Brand Name
Pipracil
Synonyms
Piperacillin AnhydrousPiperacillin
IUPAC Traditional name
potassium (2S,5R,6R)-6-[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Registration numbers
CAS Number
Properties
Physical Property
Hydrophobicity(logP)
0.3
Molecule Details
Drug Groups
approved
Description
Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]
Indication
For the treatment of polymicrobial infections.
Pharmacology
Piperacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Piperacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Piperacillin results from the inhibition of cell wall synthesis and is mediated through Piperacillin binding to penicillin binding proteins (PBPs). Piperacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation
Largely not metabolized.
Absorption
Not absorbed following oral administration.
Half Life
36-72 minutes
Elimination
As with other penicillins, PIPRACIL is eliminated primarily by glomerular filtration and tubular secretion; it is excreted rapidly as unchanged drug in high concentrations in the urine. Because PIPRACIL is excreted by the biliary route as well as by the renal route, it can be used safely in appropriate dosage in patients with severely restricted kidney function.
Distribution
* 101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]
Clearance
* 32?-?41 mL/min/1.73?m2
* 124?-?160 mL/min/1.73?m2 [older pediatric patients]
References
• Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: 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. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. [Pubmed]
External Links
Molecular Spectra
No Data Available
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References
• Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: 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. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. Pubmed