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
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 Key
Piperacillin SodiumM98T69Q7HP59703-84-3WCMIIGXFCMNQDS-IDYPWDAWSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Piperacillin for InjectionPowder, for solution4 gIntramuscular; IntravenousFresenius Kabi2004-08-05Not applicableCanada
Piperacillin for InjectionPowder, for solution2 gIntramuscular; IntravenousHospira, Inc.2003-01-232017-07-17Canada
Piperacillin for InjectionPowder, for solution3 gIntramuscular; IntravenousHospira, Inc.2003-01-23Not applicableCanada
Piperacillin for InjectionPowder, for solution3 gIntramuscular; IntravenousFresenius Kabi2004-08-05Not applicableCanada
Piperacillin for InjectionPowder, for solution4 gIntramuscular; IntravenousHospira, Inc.2003-01-232017-07-17Canada
Piperacillin for InjectionPowder, for solution2 gIntramuscular; IntravenousFresenius Kabi2004-07-29Not 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
International/Other Brands
Ecosette (Farmaceutici T.S.) / Farecillin (SF Group) / Penmalin (Sawai Seiyaku) / Pentcillin (Toyama Kagaku) / Peracin (Pharmadica) / Piciliant (Shiono Kemikaru) / Picillin (CT) / Picillina (CCPC) / Piperac (Klonal) / Pipracil (Wyeth) / Stepten (Aversi) / Tronazam (Richmond)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Jamp-pip/tazPiperacillin (4 g) + Tazobactam (0.5 g)Powder, for solutionIntravenousJamp Pharma Corporation2014-03-12Not applicableCanada
Mylan-piperacillin and Tazobactam for InjectionPiperacillin (2 g) + Tazobactam (0.25 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-piperacillin and Tazobactam for InjectionPiperacillin (4 g) + Tazobactam (0.5 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-piperacillin and Tazobactam for InjectionPiperacillin (3 g) + Tazobactam (0.375 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Piperacillin / Tazobactam Powder for InjectionPiperacillin (3 g) + Tazobactam (0.375 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionPiperacillin (4 g) + Tazobactam (0.5 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionPiperacillin (2 g) + Tazobactam (0.25 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin and TazobactamPiperacillin Sodium (4 g/1) + Tazobactam sodium (.5 g/1)Injection, powder, lyophilized, for solutionIntravenous; ParenteralHospira, Inc.2010-10-21Not applicableUs
Piperacillin and TazobactamPiperacillin Sodium (4 g/20mL) + Tazobactam sodium (.5 g/20mL)Injection, powder, for solutionIntravenousWG Critical Care, LLC2009-10-13Not applicableUs
Piperacillin and TazobactamPiperacillin Sodium (36 g/180mL) + Tazobactam sodium (4.5 g/180mL)Injection, powder, for solutionIntravenousWG Critical Care, LLC2009-10-20Not applicableUs
Categories
UNII
9I628532GX
CAS number
66258-76-2
Weight
Average: 517.555
Monoisotopic: 517.163118933
Chemical Formula
C23H27N5O7S
InChI Key
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][[email protected]]12SC(C)(C)[[email protected]@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.

TargetActionsOrganism
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
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
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
annamycinThe serum concentration of annamycin can be decreased when it is combined with Piperacillin.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, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Piperacillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Piperacillin.Experimental
ChlortetracyclineThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
ClorindionePiperacillin may increase the anticoagulant activities of Clorindione.Experimental
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
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Piperacillin.Experimental
DicoumarolPiperacillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Piperacillin.Investigational, Vet Approved
DiphenadionePiperacillin may increase the anticoagulant activities of Diphenadione.Experimental
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, Investigational
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
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Piperacillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Piperacillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Piperacillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Piperacillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Piperacillin.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Piperacillin.Approved, Investigational, 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
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Piperacillin.Experimental
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, Investigational
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, Investigational
PhenprocoumonPiperacillin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
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
PlazomicinThe serum concentration of Plazomicin 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, Investigational, 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, Investigational
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Piperacillin.Investigational
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, Investigational, 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
TioclomarolPiperacillin may increase the anticoagulant activities of Tioclomarol.Experimental
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
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Piperacillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Piperacillin.Experimental
Food Interactions
Not 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
Human Metabolome Database
HMDB14464
KEGG Drug
D00466
KEGG Compound
C14034
PubChem Compound
43672
PubChem Substance
46504757
ChemSpider
39798
BindingDB
50240426
ChEBI
8232
ChEMBL
CHEMBL702
Therapeutic Targets Database
DAP001164
PharmGKB
PA450975
HET
WPP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Piperacillin
ATC Codes
J01CA12 — PiperacillinJ01CR50 — Combinations of penicillinsJ01CR05 — Piperacillin and enzyme inhibitor
AHFS Codes
  • 08:12.16.16 — Extended-spectrum Penicillins
PDB Entries
3q07
MSDS
Download (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
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 ResearchBacterial Infections1
4CompletedPreventionBacterial Infections1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentBody Clearance / Diffusive and Convective Clearance / Piperacillin Tazocilline Concentrations (Cmin)1
4CompletedTreatmentDiabetes Mellitus (DM) / Diabetic Foot1
4Enrolling by InvitationTreatmentEarly Phase of Severe Sepsis and Septic Shock1
4Not Yet RecruitingOtherChronic Obstructive Pulmonary Disease (COPD) / Pseudomonas Aeruginosa / Respiratory Tract Infections (RTI)1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingTreatmentBloodstream Infections1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentAcute Renal Failure (ARF) / Shock, Septic1
4TerminatedTreatmentBloodstream Infections1
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 solutionIntravenous
Powder, for solutionIntravenous40 g
Powder, for solutionIntramuscular; Intravenous4 g
Powder, for solutionIntramuscular; Intravenous2 g
Powder, for solutionIntramuscular; Intravenous3 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)
US6900184No2003-04-142023-04-14Us
US8133883No2003-04-142023-04-14Us
US7915229No2003-04-142023-04-14Us
US6207661No1999-02-222019-02-22Us

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0013090000-813104cd60a9ea3a3859
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0096000000-b0dafe2b22b2f860c497
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0191000000-59dd52b81e08a7665c9f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-1590000000-b8040d8994155855d7d1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00ec-7940000000-d2ff9e1e0c9df03f7bd7
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0094000000-2b4357e65d4f2c23da13
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udl-0890000000-1d19bc9caab1a3f5b623
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000f-0910000000-0c815f0f7a25577e636c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-70932882f6df40d54777
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-2bb7a0e3a556eadb090d

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Penicillins / 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
show 14 more
Substituents
Alpha 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
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (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 ...
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 December 10, 2017 17:18