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Identification
NamePiperacillin
Accession NumberDB00319  (APRD00325)
TypeSmall Molecule
GroupsApproved
Description

Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]

Structure
Thumb
Synonyms
(2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Piperacilina
Piperacillin
Piperacillin Anhydrous
Piperacillina
Pipéracilline
Piperacillinum
External Identifiers
  • BL-P 1908
  • CI 867
  • CL 227193
  • T 1220
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Piperacillin for Injectionpowder for solution2 gintramuscular; intravenousHospira Healthcare Corporation2003-01-23Not applicableCanada
Piperacillin for Injectionpowder for solution4 gintramuscular; intravenousFresenius Kabi Canada Ltd2004-08-05Not applicableCanada
Piperacillin for Injectionpowder for solution3 gintramuscular; intravenousFresenius Kabi Canada Ltd2004-08-05Not applicableCanada
Piperacillin for Injectionpowder for solution2 gintramuscular; intravenousFresenius Kabi Canada Ltd2004-07-29Not applicableCanada
Piperacillin for Injectionpowder for solution4 gintramuscular; intravenousHospira Healthcare Corporation2003-01-23Not applicableCanada
Piperacillin for Injectionpowder for solution3 gintramuscular; intravenousHospira Healthcare Corporation2003-01-23Not applicableCanada
Pipracil Inj 2gm/vialpowder for solution2 gintramuscular; intravenousLederle Cyanamid Canada Inc.1982-12-312000-08-02Canada
Pipracil Inj 3gm/vialpowder for solution3 gintramuscular; intravenousLederle Cyanamid Canada Inc.1982-12-312000-08-02Canada
Pipracil Inj 4gm/vialpowder for solution4 gintramuscular; intravenousLederle Cyanamid Canada Inc.1982-12-312000-08-02Canada
Pipracil Pharmacy Bulk 40gm/vialpowder for solution40 gintravenousCyanamid Canada Inc.1992-12-312000-08-22Canada
Pipracil Pharmacy Bulk Vial-pws IV 40g/vialpowder for solution40 gintravenousWyeth Ayerst Canada Inc.1999-10-132002-10-29Canada
Pipracil-pws Im IV 4g/vialpowder for solution4 gintramuscular; intravenousWyeth Canada1999-10-132004-06-28Canada
Pipracil-pws IV Im 2g/vialpowder for solution2 gintramuscular; intravenousWyeth Canada2000-03-132004-06-28Canada
Pipracil-pws IV Im 3g/vialpowder for solution3 gintramuscular; intravenousWyeth Canada1999-10-132004-06-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EcosetteFarmaceutici T.S.
FarecillinSF Group
PenmalinSawai Seiyaku
PentcillinToyama Kagaku
PeracinPharmadica
PiciliantShiono Kemikaru
PicillinCT
PicillinaCCPC
PiperacKlonal
PipracilWyeth
SteptenAversi
TronazamRichmond
Brand mixtures
NameLabellerIngredients
Jamp-pip/tazJamp Pharma Corporation
Mylan-piperacillin and Tazobactam for InjectionMylan Pharmaceuticals Ulc
Piperacillin / Tazobactam Powder for InjectionTeva Canada Limited
Piperacillin and TazobactamHospira, Inc
Piperacillin and Tazobactam for InjectionApotex Inc
Piperacillin Sodium/tazobactam Sodium Powder for InjectionSandoz Canada Incorporated
Piperacillin, TazobactamSagent Pharmaceuticals
Piperacillin/tazobactam for InjectionPharma Strides Canada Corporation
TazocinPfizer Canada Inc
Tazocin Pws IV 2g Piperacillin-.25g Tazobac.Lederle Cyanamid Canada Inc.
Tazocin Pws IV 3g Piperacillin-.375g TazobacLederle Cyanamid Canada Inc.
Tazocin Pws IV 4g Piperacillin-.5g Tazobac.Lederle Cyanamid Canada Inc.
Vpi-piperacillin and Tazobactam for InjectionVpi Pharmaceuticals Inc
ZosynWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Zosyn In Galaxy ContainersWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Zosyn Pharmacy Bulk PackageWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Salts
Name/CASStructureProperties
Piperacillin Sodium
ThumbNot applicableDBSALT001067
Categories
UNIIX00B0D5O0E
CAS number66258-76-2
WeightAverage: 517.555
Monoisotopic: 517.163118933
Chemical FormulaC23H27N5O7S
InChI KeyInChIKey=IVBHGBMCVLDMKU-GXNBUGAJSA-N
InChI
InChI=1S/C23H27N5O7S/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)/t13-,14-,15+,20-/m1/s1
IUPAC Name
(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-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=CC=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-carbamoyl-alpha-amino acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Piperazine-1-carboxamide
  • Dioxopiperazine
  • N-alkylpiperazine
  • Ureide
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Urea
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of polymicrobial infections.
PharmacodynamicsPiperacillin 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 actionBy 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.
Related Articles
AbsorptionNot absorbed following oral administration.
Volume of distribution
  • 101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]
Protein bindingNot Available
Metabolism

Largely not metabolized.

Route of eliminationAs 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 life36-72 minutes
Clearance
  • 32 - 41 mL/min/1.73 m2
  • 124 - 160 mL/min/1.73 m2 [older pediatric patients]
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8753
Blood Brain Barrier-0.9958
Caco-2 permeable-0.7121
P-glycoprotein substrateSubstrate0.9442
P-glycoprotein inhibitor INon-inhibitor0.6043
P-glycoprotein inhibitor IINon-inhibitor0.991
Renal organic cation transporterNon-inhibitor0.8791
CYP450 2C9 substrateNon-substrate0.7392
CYP450 2D6 substrateNon-substrate0.8002
CYP450 3A4 substrateSubstrate0.5889
CYP450 1A2 substrateNon-inhibitor0.8597
CYP450 2C9 inhibitorNon-inhibitor0.7568
CYP450 2D6 inhibitorNon-inhibitor0.9002
CYP450 2C19 inhibitorNon-inhibitor0.7289
CYP450 3A4 inhibitorNon-inhibitor0.8856
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.948
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9021
BiodegradationNot ready biodegradable0.8093
Rat acute toxicity2.3925 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Inhibitor0.6173
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Istituto biochimico italiano giovanni lorenzini
  • Wyeth pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionintravenous
Injection, powder, lyophilized, for solutionintravenous; parenteral
Powder for solutionintramuscular; intravenous2 g
Powder for solutionintramuscular; intravenous3 g
Powder for solutionintramuscular; intravenous4 g
Powder for solutionintravenous
Powder for solutionintravenous40 g
Injection, powder, lyophilized, for solutionintravenous
Injection, solutionintravenous
Prices
Unit descriptionCostUnit
Piperacillin 40 gm bulk vial154.8USD vial
Piperacillin 4 gm vial16.7USD vial
Piperacillin 3 gm vial12.53USD vial
Piperacillin 2 gm vial8.35USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6207661 No1999-02-222019-02-22Us
US6900184 No2003-04-142023-04-14Us
US7915229 No2003-04-142023-04-14Us
US8133883 No2003-04-142023-04-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.119 mg/mLALOGPS
logP0.67ALOGPS
logP-0.26ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.43 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.3 m3·mol-1ChemAxon
Polarizability51.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

Bruce E. Haeger, “Composition of matter comprising a low bulk density lyophilized preparation of Sodium Piperacillin.” U.S. Patent US4534977, issued October, 1984.

US4534977
General References
  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:16940077 ]
External Links
ATC CodesJ01CA12J01CR05
AHFS Codes
  • 08:12.16.16
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (50.5 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolPiperacillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Piperacillin.
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Piperacillin.
BiotinThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Biotin.
DemeclocyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Demeclocycline.
DicoumarolPiperacillin may increase the anticoagulant activities of Dicoumarol.
DoxycyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Doxycycline.
FlucloxacillinThe serum concentration of Flucloxacillin can be increased when it is combined with Piperacillin.
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Piperacillin.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Piperacillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Piperacillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Piperacillin.
MinocyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Minocycline.
Mycophenolate mofetilThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Piperacillin resulting in a loss in efficacy.
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Piperacillin resulting in a loss in efficacy.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Piperacillin.
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Piperacillin.
OxytetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Oxytetracycline.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Piperacillin.
ProbenecidThe serum concentration of Piperacillin can be increased when it is combined with Probenecid.
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Piperacillin.
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Piperacillin.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Piperacillin.
TetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Tetracycline.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Piperacillin.
VancomycinPiperacillin may increase the nephrotoxic activities of Vancomycin.
VecuroniumPiperacillin may increase the neuromuscular blocking activities of Vecuronium.
WarfarinPiperacillin may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not Available
Gene Name:
pbp3
Uniprot ID:
Q75Y35
Molecular Weight:
45209.84 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M6
Molecular Weight:
73872.305 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp2a
Uniprot ID:
Q8DNB6
Molecular Weight:
80797.94 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp1b
Uniprot ID:
Q7CRA4
Molecular Weight:
89479.92 Da
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:7447421 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
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:10411577 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on July 01, 2016 01:52