U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PIPERACILLIN ANHYDROUS

SMILES

[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=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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZOSYN

Approved Use

ZOSYN 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 Date

1993
Curative
ZOSYN

Approved Use

ZOSYN 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 Date

1993
Curative
ZOSYN

Approved Use

ZOSYN 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 Date

1993
Curative
ZOSYN

Approved Use

ZOSYN 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 Date

1993
Curative
ZOSYN

Approved Use

ZOSYN 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 Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
150 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
344.3 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.85 h
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

Doses

DosePopulationAdverse 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%)
Injection site pain (2%)
Injection site erythema (2%)
Injection site induration (2%)
Diarrhea (2%)
Loose stools (2%)
Rash (1%)
Sources:
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%)
Injection site pain (2%)
Injection site erythema (2%)
Injection site induration (2%)
Diarrhea (2%)
Loose stools (2%)
Rash (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Rahnella aquatilis bacteremia in a patient with relapsed acute lymphoblastic leukemia.
2001
Infections caused by Flavimonas oryzihabitans.
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
[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
Renal abscess: recovery without hospitalization and drainage.
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
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
Piperacillin, beta-lactam inhibitor plus gentamicin as empirical therapy of a sequential regimen in febrile neutropenia of pediatric cancer patients.
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
Cholangiopathy after short-term administration of piperacillin and imipenem/cilastatin.
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
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
Evaluating possible pharmacokinetic interactions between tobramycin, piperacillin, and a combination of piperacillin and tazobactam in patients with various degrees of renal impairment.
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
Patents

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 Fri Dec 15 15:47:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:47:14 GMT 2023
Record UNII
9I628532GX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERACILLIN ANHYDROUS
Common Name English
Piperacillin [WHO-DD]
Common Name English
PIPERACILLIN [MART.]
Common Name English
PERACIN
Brand Name English
PIPERACILLIN, ANHYDROUS
Common Name English
PIPERACILLIN [JAN]
Common Name English
piperacillin [INN]
Common Name English
PIPERACILLIN [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175497
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
WHO-ATC J01CA12
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
LIVERTOX NBK548463
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NCI_THESAURUS C1558
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
LIVERTOX NBK548825
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
Code System Code Type Description
FDA UNII
9I628532GX
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
CAS
61477-96-1
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
DAILYMED
9I628532GX
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023482
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
CHEBI
8232
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
NCI_THESAURUS
C61891
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
INN
4296
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
RXCUI
1546000
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY RxNorm
EVMPD
SUB09867MIG
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
262-811-8
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
SMS_ID
100000092185
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
MERCK INDEX
m8845
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY Merck Index
PUBCHEM
43672
Created by admin on Fri Dec 15 15:47:14 GMT 2023 , Edited by admin on Fri Dec 15 15:47:14 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
The protein binding of either piperacillin or tazobactam is unaffected by the presence of the other compound.
BINDING
SOLVATE->ANHYDROUS
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC INTRAVENOUS ADMINISTRATION