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Piperacillin

Catalog No. DB00319 Name DrugBank
CAS Number 66258-76-2 Website http://www.ualberta.ca/
M. F. C23H26N5NaO7S Telephone (780) 492-3111
M. W. 539.53661 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 204

SYNONYMS

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
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
Brand Name
Pipracil
Synonyms
Piperacillin Anhydrous

DATABASE IDS

CAS Number 66258-76-2

PROPERTIES

Hydrophobicity(logP) 0.3

DETAILS

Description (English)
Item Information
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
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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