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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

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

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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 18:08:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:08:33 GMT 2025
Record UNII
9I628532GX
Record Status Validated (UNII)
Record Version
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Name Type Language
PIPERACILLIN ANHYDROUS
Common Name English
PERACIN
Preferred Name English
Piperacillin [WHO-DD]
Common Name English
PIPERACILLIN [MART.]
Common 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 Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
WHO-ATC J01CA12
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
LIVERTOX NBK548463
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NCI_THESAURUS C1558
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
LIVERTOX NBK548825
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
Code System Code Type Description
FDA UNII
9I628532GX
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
CAS
61477-96-1
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
DAILYMED
9I628532GX
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID2023482
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
CHEBI
8232
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
NCI_THESAURUS
C61891
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
INN
4296
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
RXCUI
1546000
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY RxNorm
EVMPD
SUB09867MIG
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
262-811-8
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
SMS_ID
100000092185
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY
MERCK INDEX
m8845
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
PRIMARY Merck Index
PUBCHEM
43672
Created by admin on Mon Mar 31 18:08:33 GMT 2025 , Edited by admin on Mon Mar 31 18:08:33 GMT 2025
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