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
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: |
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 |
---|---|---|
Fresh vs aged benzylpenicillin on non-IgE responses in mice. | 1998 Jan |
|
Hypercoagulopathy with piperacillin administration in osteomyelitis. | 2000 May |
|
[Use of the Etest method for antimicrobial susceptibility testing of obligate anaerobes]. | 2001 |
|
[Achromobacter xylosoxidans bacteremia in a patient with community-acquired pneumonia]. | 2001 |
|
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 |
|
Renal abscess: recovery without hospitalization and drainage. | 2001 Aug |
|
[Interventional ERCP in patients with cholestasis. Degree of biliary bacterial colonization and antibiotic resistance]. | 2001 Dec |
|
[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa]. | 2001 Feb |
|
Impaired target site penetration of beta-lactams may account for therapeutic failure in patients with septic shock. | 2001 Feb |
|
The role of topical antibiotic prophylaxis in patients undergoing contaminated head and neck surgery with flap reconstruction. | 2001 Feb |
|
Cost efficacy of tazobactam/piperacillin versus imipenem/cilastatin in the treatment of intra-abdominal infection. | 2001 Jan |
|
Possible role of cellular immunity: a case of cellulitis. | 2001 Jan |
|
A randomized prospective multicentre trial of cefpirome versus piperacillin-tazobactam in febrile neutropenia. | 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 |
|
Ultraviolet recall-like phenomenon occurring after piperacillin, tobramycin, and ciprofloxacin therapy. | 2001 Jun |
|
Effect of beta-lactam antibiotics on the in vitro development of resistance in Pseudomonas aeruginosa. | 2001 Mar |
|
Treatment of nosocomial postoperative pneumonia in cancer patients: a prospective randomized study. | 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 |
|
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 |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Molecular epidemiology of antibiotic-resistant gram-negative bacilli in a neonatal intensive care unit during a nonoutbreak period. | 2001 Nov |
|
CAPD-associated peritonitis caused by Alcaligenes xylosoxidans sp. xylosoxidans. | 2001 Nov-Dec |
|
A multicenter, double-blind, placebo-controlled trial comparing piperacillin-tazobactam with and without amikacin as empiric therapy for febrile neutropenia. | 2001 Oct 15 |
|
Piperacillin/Tazobactam versus cefotaxime plus metronidazole for treatment of children with intra-abdominal infections requiring surgery. | 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 |
|
Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting. | 2001 Sep |
|
Penetration of piperacillin/tazobactam (4 g/500 mg) into synovial tissue. | 2002 Feb |
|
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 |
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).
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Classification Tree | Code System | Code | ||
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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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ACTIVE MOIETY
SUBSTANCE RECORD