Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H27N5O7S |
Molecular Weight | 517.555 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)C4=CC=CC=C4)C(=O)C1=O
InChI
InChIKey=IVBHGBMCVLDMKU-GXNBUGAJSA-N
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
Molecular Formula | C23H27N5O7S |
Molecular Weight | 517.555 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68010878
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68010878
Piperacillin is a semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic which exerts bactericidal activity by inhibiting septum formation and cell wall synthesis of susceptible bacteria. Piperacillin sodium salt is used in combination with the β-lactamase inhibitor tazobactam sodium (ZOSYN®) for the treatment of patients with moderate to severe infections caused by susceptible bacteria.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) |
940.0 nM [IC50] | ||
Target ID: P0A3M6 Gene ID: 933948.0 Gene Symbol: penA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) |
51.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ZOSYN Approved UseZOSYN is a combination penicillin-class antibacterial and β-lactamase inhibitor indicated for treatment of:
- Intra-abdominal infections;
- Skin and skin structure infections;
- Female pelvic infections;
- Community-acquired pneumonia;
- Nosocomial pneumonia. Launch Date1993 |
|||
Curative | ZOSYN Approved UseZOSYN is a combination penicillin-class antibacterial and β-lactamase inhibitor indicated for treatment of:
- Intra-abdominal infections;
- Skin and skin structure infections;
- Female pelvic infections;
- Community-acquired pneumonia;
- Nosocomial pneumonia. Launch Date1993 |
|||
Curative | ZOSYN Approved UseZOSYN is a combination penicillin-class antibacterial and β-lactamase inhibitor indicated for treatment of:
- Intra-abdominal infections;
- Skin and skin structure infections;
- Female pelvic infections;
- Community-acquired pneumonia;
- Nosocomial pneumonia. Launch Date1993 |
|||
Curative | ZOSYN Approved UseZOSYN is a combination penicillin-class antibacterial and β-lactamase inhibitor indicated for treatment of:
- Intra-abdominal infections;
- Skin and skin structure infections;
- Female pelvic infections;
- Community-acquired pneumonia;
- Nosocomial pneumonia. Launch Date1993 |
|||
Curative | ZOSYN Approved UseZOSYN is a combination penicillin-class antibacterial and β-lactamase inhibitor indicated for treatment of:
- Intra-abdominal infections;
- Skin and skin structure infections;
- Female pelvic infections;
- Community-acquired pneumonia;
- Nosocomial pneumonia. Launch Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
150 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23590897/ |
4.5 g single, intravenous dose: 4.5 g route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPERACILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
344.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23590897/ |
4.5 g single, intravenous dose: 4.5 g route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPERACILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23590897/ |
4.5 g single, intravenous dose: 4.5 g route of administration: Intravenous experiment type: SINGLE co-administered: |
PIPERACILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Thrombophlebitis, Injection site pain... Other AEs: Thrombophlebitis (4%) Sources: Injection site pain (2%) Injection site erythema (2%) Injection site induration (2%) Diarrhea (2%) Loose stools (2%) Rash (1%) |
4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Thrombophlebitis, Injection site pain... Other AEs: Thrombophlebitis (4%) Sources: Injection site pain (2%) Injection site erythema (2%) Injection site induration (2%) Diarrhea (2%) Loose stools (2%) Rash (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Rash | 1% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Diarrhea | 2% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site erythema | 2% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site induration | 2% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site pain | 2% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Loose stools | 2% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Thrombophlebitis | 4% | 2 g 4 times / day multiple, intramuscular Dose: 2 g, 4 times / day Route: intramuscular Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Rash | 1% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Diarrhea | 2% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site erythema | 2% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site induration | 2% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Injection site pain | 2% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Loose stools | 2% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Thrombophlebitis | 4% | 4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/ |
no | |||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/ |
no | |||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/ |
no | |||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11850258/ |
no | |||
weak [IC50 1140 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Km 172 uM] | ||||
yes [Km 37 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
Peritonitis in automated peritoneal dialysis: antibiotic therapy and pharmacokinetics. | 2001 |
|
Rahnella aquatilis bacteremia in a patient with relapsed acute lymphoblastic leukemia. | 2001 |
|
[Achromobacter xylosoxidans bacteremia in a patient with community-acquired pneumonia]. | 2001 |
|
Infections caused by Flavimonas oryzihabitans. | 2001 Apr |
|
Chronic granulomatous disease: a case report. | 2001 Apr |
|
Monotherapy with meropenem versus combination therapy with piperacillin plus amikacin as empiric therapy for neutropenic fever in children with lymphoma and solid tumors. | 2001 Apr-Jun |
|
An observational study on the epidemiology of respiratory tract bacterial pathogens and their susceptibility to four injectable beta-lactam antibiotics: piperacillin, piperacillin/tazobactam, ceftazidime and ceftriaxone. | 2001 Aug |
|
[Antimicrobial activities and mechanisms of carbapenem resistance in clinical isolates of carbapenem-resistant Pseudomonas aeruginosa and Acinetobacter spp]. | 2001 Aug |
|
Pharmacokinetic and pharmacodynamic profile of high dose extended interval piperacillin-tazobactam. | 2001 Aug |
|
Survey of antibiotic resistance in Pseudomonas aeruginosa by The Tokyo Johoku Association of Pseudomonas Studies. | 2001 Dec |
|
Treatment of pulmonary nocardiosis in heart-transplant patients: importance of susceptibility studies. | 2001 Dec |
|
Influence of previous exposure to antibiotic therapy on the susceptibility pattern of Pseudomonas aeruginosa bacteremic isolates. | 2001 Dec 1 |
|
Antibacterial activity of 41 antimicrobials tested against over 2773 bacterial isolates from hospitalized patients with pneumonia: I--results from the SENTRY Antimicrobial Surveillance Program (North America, 1998). | 2001 Feb |
|
Impaired target site penetration of beta-lactams may account for therapeutic failure in patients with septic shock. | 2001 Feb |
|
Study on fluorescent property of degrading products of piperacillin and its analytical application. | 2001 Feb |
|
Increased antibiotic resistance of E. coli exposed to static magnetic fields. | 2001 Feb |
|
Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations. | 2001 Feb |
|
Cost efficacy of tazobactam/piperacillin versus imipenem/cilastatin in the treatment of intra-abdominal infection. | 2001 Jan |
|
[Multicentre clinical trial on efficacy and safety of domestic piperacillin/tazobactam for treatment of acute bacterial infections]. | 2001 Jan 10 |
|
[Surveillance of bacterial resistance in Shanghai]. | 2001 Jan 10 |
|
Acinetobacter infections in patients with human immunodeficiency virus infection: microbiological and clinical epidemiology. | 2001 Jan-Feb |
|
Epidemiology and frequency of resistance among pathogens causing urinary tract infections in 1,510 hospitalized patients: a report from the SENTRY Antimicrobial Surveillance Program (North America). | 2001 Jul |
|
Pulmonary infiltration with eosinophilia (PIE) syndrome induced by antibiotics, PIPC and TFLX during cancer treatment. | 2001 Jul |
|
Is levofloxacin as active as ciprofloxacin against Pseudomonas aeruginosa? | 2001 Jul-Aug |
|
[Mycoplasma pneumonia complicated by acute renal failure]. | 2001 Jun |
|
Surveillance of bacterial resistance among isolates in Shanghai in 1999. | 2001 Jun |
|
Complicated urinary tract infections in patients with voiding dysfunction. | 2001 Jun |
|
Cholangiopathy after short-term administration of piperacillin and imipenem/cilastatin. | 2001 Jun |
|
Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test. | 2001 Jun |
|
Multi-drug resistant Pseudomonas aeruginosa outbreak in a burns unit--an infection control study. | 2001 Mar |
|
Performance of the VITEK2 system for identification and susceptibility testing of routine Enterobacteriaceae clinical isolates. | 2001 May |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Hand infections in patients with diabetes mellitus. | 2001 Nov |
|
Stability of piperacillin and ticarcillin in AutoDose infusion system bags. | 2001 Nov |
|
In vitro antimicrobial susceptibility of Aerococcus urinae to 14 antibiotics, and time-kill curves for penicillin, gentamicin and vancomycin. | 2001 Nov |
|
Immediate remission obtained by minocycline in a patient with histiocytic necrotizing lymphadenitis. | 2001 Oct |
|
Nosocomial pneumonia in pediatric patients: practical problems and rational solutions. | 2002 |
|
Multidrug-resistant Pseudomonas aeruginosa bloodstream infections: analysis of trends in prevalence and epidemiology. | 2002 Feb |
|
Antibiotic resistance patterns of bacterial isolates from blood in San Francisco County, California, 1996-1999. | 2002 Feb |
|
Penetration of piperacillin/tazobactam (4 g/500 mg) into synovial tissue. | 2002 Feb |
|
Antibiotic-induced recurring interstitial nephritis. | 2002 Jan |
|
Surveillance for antimicrobial resistance in Croatia. | 2002 Jan |
Sample Use Guides
The usual total daily dose of ZOSYN® for adults is 3.375 g every six hours totaling 13.5 g (12.0 g piperacillin/1.5 g tazobactam). The usual duration of ZOSYN® treatment is from 7 to 10 days. ZOSYN® should be administered by intravenous infusion over 30 minutes.
Route of Administration:
Intravenous
The MIC values for piperacillin/tazobactam were: 1-4 ug/ml (Escherichia coli ATCC 25922), 0.5-2 ug/ml (Escherichia coli ATCC 35218), 1-8 ug/ml (Pseudomonas aeruginosa ATCC 27853), 0.06-0.5 ug/ml (Haemophilus influenzae ATCC 49247), 0.25-2 ug/ml (Staphylococcus aureus ATCC 29213), 0.12-0.5 ug/ml (Bacteroides fragilis ATCC 25285), 4-16 ug/ml (Bacteroides thetaiotaomicron ATCC 29741).
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:08:33 GMT 2025
by
admin
on
Mon Mar 31 18:08:33 GMT 2025
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Record UNII |
9I628532GX
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175497
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WHO-ATC |
J01CA12
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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N0000011281
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NDF-RT |
N0000011281
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LIVERTOX |
NBK548463
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NCI_THESAURUS |
C1558
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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LIVERTOX |
NBK548825
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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61477-96-1
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9I628532GX
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DTXSID2023482
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8232
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C61891
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4296
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1546000
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SUB09867MIG
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262-811-8
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100000092185
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m8845
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43672
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
The protein binding of either piperacillin or tazobactam is unaffected by the presence of the other compound.
BINDING
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SOLVATE->ANHYDROUS | |||
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EXCRETED UNCHANGED |
URINE
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
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INTRAVENOUS ADMINISTRATION |
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