Banner
targets (4) transporters (1)
for drugs
Identification
Name Piperacillin
Accession Number DB00319 (APRD00325)
Type small molecule
Groups approved
Description

Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Piperacillin Anhydrous
Brand names
  • Pipracil
Brand name mixtures
  • Tazocin (Piperacillin (Piperacillin Sodium) + Tazobactam (Tazobactam Sodium))
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 66258-76-2
Weight Average: 539.537
Monoisotopic: 539.145063576
Chemical Formula C23H26N5NaO7S
InChI Key InChIKey=WCMIIGXFCMNQDS-IDYPWDAWSA-M
InChI
InChI=1S/C23H27N5O7S.Na/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28;/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34);/q;+1/p-1/t13-,14-,15+,20-;/m1./s1
Plain Text
IUPAC Name
sodium (2S,5R,6R)-6-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=CC=C1)C([O-])=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Penicillins
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Piperazines
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Ureas and Derivatives
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiazolidines
Pharmacology
Indication For the treatment of polymicrobial infections.
Pharmacodynamics 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.
Mechanism of action By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Piperacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Piperacillin interferes with an autolysin inhibitor.
Absorption Not absorbed following oral administration.
Volume of distribution
  • 101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]
Protein binding Not Available
Metabolism

Largely not metabolized.
Route of 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.
Half life 36-72 minutes
Clearance
  • 32 - 41 mL/min/1.73 m2
  • 124 - 160 mL/min/1.73 m2 [older pediatric patients]
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Istituto biochimico italiano giovanni lorenzini
  • Wyeth pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Piperacillin 40 gm bulk vial 154.8 USD vial
Piperacillin 4 gm vial 16.7 USD vial
Piperacillin 3 gm vial 12.53 USD vial
Piperacillin 2 gm vial 8.35 USD vial
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 0.3 PhysProp
Predicted Properties
Property Value Source
water solubility 3.40e-01 g/l ALOGPS
logP 1.21 ALOGPS
logP -0.26 ChemAxon Molconvert
logS -3.20 ALOGPS
pKa 11.60 ChemAxon Molconvert
hydrogen acceptor count 7 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 159.26 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 137.13 ChemAxon Molconvert
polarizability 51.25 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
Resource Link
KEGG Drug D00466 Link_out
KEGG Compound C07361 Link_out
PubChem Compound 23666879 Link_out
PubChem Substance 46504757 Link_out
ChemSpider 39798 Link_out
ChEBI 8232 Link_out
ChEMBL 8232 Link_out
Therapeutic Targets Database DAP001164 Link_out
PharmGKB PA450975 Link_out
Drug Product Database 2248939 Link_out
RxList http://www.rxlist.com/cgi/generic3/piperacillin.htm Link_out
Drugs.com http://www.drugs.com/cdi/piperacillin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Piperacillin Link_out
ATC Codes
  • J01CA12
AHFS Codes
  • 08:12.16.16
PDB Entries Not Available
FDA label Not Available
MSDS show (50.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

2. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

3. Penicillin-binding protein 2a

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q8DNB6 Link_out
Gene: pbp2a
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

4. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out
Gene: pbp1b Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:02

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.