Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H26N5O7S.Na |
| Molecular Weight | 539.537 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](NC(=O)N3CCN(CC)C(=O)C3=O)C4=CC=CC=C4)C([O-])=O
InChI
InChIKey=WCMIIGXFCMNQDS-IDYPWDAWSA-M
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
| Molecular Formula | C23H26N5O7S |
| Molecular Weight | 516.547 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 Date7.5116157E11 |
|||
| 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 Date7.5116157E11 |
|||
| 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 Date7.5116157E11 |
|||
| 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 Date7.5116157E11 |
|||
| 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 Date7.5116157E11 |
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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains 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 Condition: serious infections caused by susceptible strains Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Peritonitis in automated peritoneal dialysis: antibiotic therapy and pharmacokinetics. | 2001 |
|
| [Use of the Etest method for antimicrobial susceptibility testing of obligate anaerobes]. | 2001 |
|
| Piperacillin/tazobactam: a pharmacoeconomic review of its use in moderate to severe bacterial infections. | 2001 |
|
| Infections caused by Flavimonas oryzihabitans. | 2001 Apr |
|
| 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 |
|
| Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China. | 2001 Aug |
|
| Antimicrobial susceptibility of respiratory isolates of Enterobacteriaceae and Staphylococcus aureus in Italy: incidence and trends over the period 1997-1999. | 2001 Dec |
|
| Survey of antibiotic resistance in Pseudomonas aeruginosa by The Tokyo Johoku Association of Pseudomonas Studies. | 2001 Dec |
|
| [Interventional ERCP in patients with cholestasis. Degree of biliary bacterial colonization and antibiotic resistance]. | 2001 Dec |
|
| Treatment of pulmonary nocardiosis in heart-transplant patients: importance of susceptibility studies. | 2001 Dec |
|
| Elimination of the piperacillin/tazobactam combination during continuous venovenous haemofiltration and haemodiafiltration in patients with acute renal failure. | 2001 Dec |
|
| Influence of previous exposure to antibiotic therapy on the susceptibility pattern of Pseudomonas aeruginosa bacteremic isolates. | 2001 Dec 1 |
|
| [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 |
|
| A randomized prospective multicentre trial of cefpirome versus piperacillin-tazobactam in febrile neutropenia. | 2001 Jul |
|
| [Analysis of the risk factors and drug resistance of lower respiratory tract infection by Flavobacteria]. | 2001 Jun |
|
| [Mycoplasma pneumonia complicated by acute renal failure]. | 2001 Jun |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
| Spectrum and activity of three contemporary fluoroquinolones tested against Pseudomonas aeruginosa isolates from urinary tract infections in the SENTRY Antimicrobial Surveillance Program (Europe and the Americas; 2000): more alike than different! | 2001 Nov |
|
| Hand infections in patients with diabetes mellitus. | 2001 Nov |
|
| Stability of piperacillin and ticarcillin in AutoDose infusion system bags. | 2001 Nov |
|
| Molecular epidemiology of antibiotic-resistant gram-negative bacilli in a neonatal intensive care unit during a nonoutbreak period. | 2001 Nov |
|
| In vitro antimicrobial susceptibility of Aerococcus urinae to 14 antibiotics, and time-kill curves for penicillin, gentamicin and vancomycin. | 2001 Nov |
|
| CAPD-associated peritonitis caused by Alcaligenes xylosoxidans sp. xylosoxidans. | 2001 Nov-Dec |
|
| Immediate remission obtained by minocycline in a patient with histiocytic necrotizing lymphadenitis. | 2001 Oct |
|
| A multicenter, double-blind, placebo-controlled trial comparing piperacillin-tazobactam with and without amikacin as empiric therapy for febrile neutropenia. | 2001 Oct 15 |
|
| Postantibiotic effects of eleven antimicrobials on five bacteria. | 2001 Sep |
|
| Piperacillin/Tazobactam versus cefotaxime plus metronidazole for treatment of children with intra-abdominal infections requiring surgery. | 2001 Sep |
|
| Isolation and culture of airway epithelial cells from chronically infected human lungs. | 2001 Sep |
|
| [Comparison of 2 administration protocols (continuous or discontinuous) of a time-dependent antibiotic, Tazocin]. | 2001 Sep |
|
| [Survey of the antibiotic sensitivity of Pseudomonas aeruginosa in France and the distribution of beta-lactam resistance mechanisms: the GERPB 1999 study]. | 2001 Sep |
|
| Evaluating possible pharmacokinetic interactions between tobramycin, piperacillin, and a combination of piperacillin and tazobactam in patients with various degrees of renal impairment. | 2001 Sep |
|
| Effect of mono-dose intraperitoneal cecropins in experimental septic shock. | 2001 Sep |
|
| Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting. | 2001 Sep |
|
| Distribution and prevalence of antimicrobial resistance among gram-negative isolates in intensive care units (ICU) in Belgian hospitals between 1996 and 1999. | 2001 Sep-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 |
|
| Piperacillin 2 g/tazobactam 0.5 g is as effective as imipenem 0.5 g/cilastatin 0.5 g for the treatment of acute uncomplicated pyelonephritis and complicated urinary tract infections. | 2002 Feb |
|
| In vitro activity of the aerosolized agents colistin and tobramycin and five intravenous agents against Pseudomonas aeruginosa isolated from cystic fibrosis patients in southwestern Germany. | 2002 Feb |
|
| Multicentre evaluation of the VITEK 2 Advanced Expert System for interpretive reading of antimicrobial resistance tests. | 2002 Feb |
|
| Clinafloxacin versus piperacillin/tazobactam in the treatment of severe skin and soft-tissue infections in adults at a Veterans Affairs medical center. | 2002 Jan |
|
| In vitro synergy testing of levofloxacin, ofloxacin, and ciprofloxacin in combination with aztreonam, ceftazidime, or piperacillin against Pseudomonas aeruginosa. | 2002 Jan |
|
| Clinical evaluation of the Vitek automated system with cards GNS 122 and 127 and VTK-R07.01 software for antimicrobial susceptibility testing of Pseudomonas aeruginosa. | 2002 Jan |
|
| Antibiotic-induced recurring interstitial nephritis. | 2002 Jan |
|
| Effect of piperacillin-tazobactam on clinical capillary zone electrophoresis of serum proteins. | 2002 Jan |
|
| Surveillance for antimicrobial resistance in Croatia. | 2002 Jan |
|
| Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936). | 2002 Mar |
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
Fri Dec 15 15:23:39 UTC 2023
by
admin
on
Fri Dec 15 15:23:39 UTC 2023
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| Record UNII |
M98T69Q7HP
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1558
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261-868-6
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203134
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CHEMBL702
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23666879
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757277
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M98T69Q7HP
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SUB03840MIG
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DBSALT001067
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100000089964
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C749
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M98T69Q7HP
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59703-84-3
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8233
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m8845
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DTXSID6048965
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |