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 IDs BL-P 1908 / CI 867 / CL 227193 / T 1220
Product Ingredients
IngredientUNIICASInChI KeyDetails
Piperacillin SodiumM98T69Q7HP 59703-84-3WCMIIGXFCMNQDS-IDYPWDAWSA-MDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Piperacillin for InjectionPowder, for solution2 gIntramuscular; IntravenousHospira, Inc.2003-01-23Not applicableCanada
Piperacillin for InjectionPowder, for solution3 gIntramuscular; IntravenousFresenius Kabi2004-08-05Not applicableCanada
Piperacillin for InjectionPowder, for solution3 gIntramuscular; IntravenousHospira, Inc.2003-01-23Not applicableCanada
Piperacillin for InjectionPowder, for solution2 gIntramuscular; IntravenousFresenius Kabi2004-07-29Not applicableCanada
Piperacillin for InjectionPowder, for solution4 gIntramuscular; IntravenousFresenius Kabi2004-08-05Not applicableCanada
Piperacillin for InjectionPowder, for solution4 gIntramuscular; IntravenousHospira, Inc.2003-01-23Not 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 Ltd.1999-10-132004-06-28Canada
Pipracil-pws IV Im 2g/vialPowder, for solution2 gIntramuscular; IntravenousWyeth Ltd.2000-03-132004-06-28Canada
Pipracil-pws IV Im 3g/vialPowder, for solution3 gIntramuscular; IntravenousWyeth Ltd.1999-10-132004-06-28Canada
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
Piperacillin / Tazobactam Powder for InjectionTeva
Piperacillin and TazobactamSandoz
Piperacillin and Tazobactam for InjectionApotex Corporation
Piperacillin Sodium/tazobactam Sodium Powder for InjectionSandoz Canada Incorporated
Piperacillin, TazobactamSagent Pharmaceuticals
Piperacillin/tazobactam for InjectionStrides Pharma Inc
TazocinPfizer
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
ZosynCardinal Health
Zosyn In Galaxy ContainersWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Zosyn Pharmacy Bulk PackageWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Categories
UNIIX00B0D5O0E
CAS number66258-76-2
WeightAverage: 517.555
Monoisotopic: 517.163118933
Chemical FormulaC23H27N5O7S
InChI KeyIVBHGBMCVLDMKU-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
Pharmacology
Indication

For the treatment of polymicrobial infections.

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 3Proteinyes
inhibitor
Streptococcus pneumoniaeQ75Y35 details
Penicillin-binding protein 2BProteinyes
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)P0A3M6 details
Penicillin-binding protein 2aProteinyes
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Q8DNB6 details
Penicillin-binding protein 1bProteinyes
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Q7CRA4 details
Related Articles
Absorption

Not 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 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]
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolPiperacillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Piperacillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Piperacillin.Approved, Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Piperacillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Piperacillin.Approved
BCG vaccineThe therapeutic efficacy of Bcg can be decreased when used in combination with Piperacillin.Investigational
ChlortetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Piperacillin.Approved
DemeclocyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Demeclocycline.Approved
DicoumarolPiperacillin may increase the anticoagulant activities of Dicoumarol.Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Piperacillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Piperacillin.Approved
Ethyl biscoumacetatePiperacillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FlucloxacillinThe serum concentration of Flucloxacillin can be increased when it is combined with Piperacillin.Approved
FluindionePiperacillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Piperacillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Piperacillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Piperacillin.Experimental
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Piperacillin.Approved
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Piperacillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Piperacillin.Approved
MinocyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Minocycline.Approved, Investigational
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.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Piperacillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Piperacillin.Approved
OxytetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Oxytetracycline.Approved, Vet Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Piperacillin.Approved, Investigational
PhenindionePiperacillin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonPiperacillin may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Piperacillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Piperacillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Piperacillin.Approved, Withdrawn
ProbenecidThe serum concentration of Piperacillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Piperacillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Piperacillin.Approved
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Piperacillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Piperacillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Piperacillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Piperacillin.Approved
TetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Tetracycline.Approved, Vet Approved
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Piperacillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Piperacillin.Approved
VancomycinPiperacillin may increase the nephrotoxic activities of Vancomycin.Approved
VecuroniumPiperacillin may increase the neuromuscular blocking activities of Vecuronium.Approved
WarfarinPiperacillin may increase the anticoagulant activities of Warfarin.Approved
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Piperacillin.Experimental
Food InteractionsNot 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 CodesJ01CA12 — PiperacillinJ01CR50 — Combinations of penicillinsJ01CR05 — Piperacillin and enzyme inhibitor
AHFS Codes
  • 08:12.16.16
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (50.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableInfection NOS1
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentInfection NOS1
2CompletedTreatmentCritical Illness / Hospital Acquired Infections / Pneumonia / Pyrexia / Systemic Inflammatory Response Syndrome (SIRS)1
2RecruitingTreatmentOsteomyelitis1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
3CompletedSupportive CareBone Marrow Suppression / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
3CompletedTreatmentAcute Pyelonephritis / Urinary Tract Infection Complicated1
3CompletedTreatmentInfection; Diabetic Foot1
3CompletedTreatmentNeoplasms, Hematologic1
3CompletedTreatmentPneumonia1
3Not Yet RecruitingTreatmentHospital-acquired bacterial pneumonia / Pneumonia, Hospital-Acquired / Ventilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
3RecruitingNot AvailablePneumonia, Bacterial1
3RecruitingTreatmentEnterobacteriaceae Infections1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
4CompletedNot AvailableInfections, Gram-Positive Bacterial1
4CompletedNot AvailableUrinary Tract Infections (UTIs)1
4CompletedHealth Services ResearchInfections, Bacterial1
4CompletedPreventionInfections, Bacterial1
4CompletedTreatmentBody Clearance / Diffusive and Convective Clearance / Piperacillin Tazocilline Concentrations (Cmin)1
4CompletedTreatmentDiabetes Mellitus (DM) / Diabetic Foot1
4CompletedTreatmentInfections, Bacterial1
4Enrolling by InvitationTreatmentEarly Phase of Severe Sepsis and Septic Shock1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingTreatmentBloodstream Infections2
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentAcute Renal Failure (ARF) / Shock, Septic1
4TerminatedTreatmentCystic Fibrosis (CF)1
4Unknown StatusTreatmentRespiratory Tract Infections (RTI) / Urinary Tract Infections (UTIs)1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedTreatmentAcute Appendicitis1
Not AvailableCompletedTreatmentFebrile / Hematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
Not AvailableEnrolling by InvitationNot AvailableCritical Illness1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingTreatmentAppendicitis1
Not AvailableUnknown StatusPreventionHematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
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, solutionIntravenous
Injection, powder, lyophilized, for 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0013090000-813104cd60a9ea3a3859View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0096000000-b0dafe2b22b2f860c497View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0191000000-59dd52b81e08a7665c9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1590000000-b8040d8994155855d7d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00ec-7940000000-d2ff9e1e0c9df03f7bd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0094000000-2b4357e65d4f2c23da13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udl-0890000000-1d19bc9caab1a3f5b623View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-0910000000-0c815f0f7a25577e636cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-70932882f6df40d54777View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-2bb7a0e3a556eadb090dView in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative ParentsPenicillins / N-acyl-alpha amino acids and derivatives / N-carbamoyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Piperazine carboxamides / Dioxopiperazines / N-acyl ureas / N-alkylpiperazines / Tertiary carboxylic acid amides
SubstituentsAlpha peptide / Penicillin / N-acyl-alpha amino acid or derivatives / N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Phenylacetamide / Piperazine-1-carboxamide / Dioxopiperazine
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspenicillin (CHEBI:8232 )

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
Uniprot Name:
Penicillin-binding protein 3
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:
Not Available
Specific Function:
Penicillin binding
Gene Name:
penA
Uniprot ID:
P0A3M6
Uniprot Name:
Penicillin-binding protein 2B
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
Uniprot Name:
Penicillin-binding protein 2a
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
Uniprot Name:
Penicillin-binding protein 1b
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
Uniprot Name:
Solute carrier family 22 member 6
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 ]
Drug created on June 13, 2005 07:24 / Updated on July 25, 2017 17:51