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 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 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 |
|
| Chronic granulomatous disease: a case report. | 2001 Apr |
|
| The immunomodulatory effects of gentamicin, imipenem, piperacillin and amphotericin B on LAK effector function in vitro. | 2001 Apr |
|
| Individualized pharmacokinetic monitoring results in less aminoglycoside-associated nephrotoxicity and fewer associated costs. | 2001 Apr |
|
| [Fundamental and clinical studies on beta-lactamase inhibitors]. | 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 |
|
| Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China. | 2001 Aug |
|
| [Antimicrobial susceptibility of Pseudomonas aeruginosa isolated in Fukushima Prefecture]. | 2001 Feb |
|
| Thermophilic multidrug-resistant Campylobacter fetus infection with hypersplenism and histiocytic phagocytosis in a patient with acquired immunodeficiency syndrome. | 2001 Jan 15 |
|
| Piperacillin, beta-lactam inhibitor plus gentamicin as empirical therapy of a sequential regimen in febrile neutropenia of pediatric cancer patients. | 2001 Jul |
|
| Faecal concentrations of piperacillin and tazobactam in elderly patients. | 2001 Jul |
|
| Pulmonary infiltration with eosinophilia (PIE) syndrome induced by antibiotics, PIPC and TFLX during cancer treatment. | 2001 Jul |
|
| Piperacillin with and without tazobactam against extended-spectrum beta-lactamase-producing Pseudomonas aeruginosa in a rat thigh abscess model. | 2001 Jul-Aug |
|
| Is levofloxacin as active as ciprofloxacin against Pseudomonas aeruginosa? | 2001 Jul-Aug |
|
| [Mycoplasma pneumonia complicated by acute renal failure]. | 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 |
|
| Ultraviolet recall-like phenomenon occurring after piperacillin, tobramycin, and ciprofloxacin therapy. | 2001 Jun |
|
| Efficacy and tolerability of piperacillin/tazobactam versus ceftazidime in association with amikacin for treating nosocomial pneumonia in intensive care patients: a prospective randomized multicenter trial. | 2001 Mar |
|
| Effect of beta-lactam antibiotics on the in vitro development of resistance in Pseudomonas aeruginosa. | 2001 Mar |
|
| Multi-drug resistant Pseudomonas aeruginosa outbreak in a burns unit--an infection control study. | 2001 Mar |
|
| Seroprevalence and antibiotic sensitivity of serotypes of Salmonella enterica in Greek pig herds. | 2001 Mar 31 |
|
| Performance of the VITEK2 system for identification and susceptibility testing of routine Enterobacteriaceae clinical isolates. | 2001 May |
|
| Ureidopenicillins and risk of Clostridium difficile infection. | 2001 May |
|
| Characterization of Pseudomonas aeruginosa isolates: occurrence rates, antimicrobial susceptibility patterns, and molecular typing in the global SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001 May 15 |
|
| [Comparative study of piperacillin/tazobactam versus imipenem/cilastatin in febrile neutropenia (1994-1996)]. | 2001 May 5 |
|
| Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-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 |
|
| Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting. | 2001 Sep |
|
| 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 |
|
| 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
Fri Dec 15 15:23:39 GMT 2023
by
admin
on
Fri Dec 15 15:23:39 GMT 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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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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8233
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m8845
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DTXSID6048965
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PARENT -> SALT/SOLVATE |
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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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