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

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
Structure of PIPERACILLIN SODIUM

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

HIDE SMILES / InChI

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

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
Haemolytic anaemia following treatment with piperacillin in a patient with cystic fibrosis.
1999 Mar
Hypercoagulopathy with piperacillin administration in osteomyelitis.
2000 May
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
Conjugative resistance to tazobactam plus piperacillin among extended-spectrum beta-lactamase-producing nosocomial Klebsiella pneumoniae.
2001
Infections caused by Flavimonas oryzihabitans.
2001 Apr
[Antibiotics--TAZ/PIPC, synercid, linezolid, everninomicin].
2001 Apr
[Fundamental and clinical studies on beta-lactamase inhibitors].
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
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
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
[Antimicrobial susceptibility of Pseudomonas aeruginosa isolated in Fukushima Prefecture].
2001 Feb
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
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
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
[Mycoplasma pneumonia complicated by acute renal failure].
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
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
Performance of the VITEK2 system for identification and susceptibility testing of routine Enterobacteriaceae clinical isolates.
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
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
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
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
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
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
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
Antibiotic-induced recurring interstitial nephritis.
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 Fri Dec 15 15:23:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:39 GMT 2023
Record UNII
M98T69Q7HP
Record Status Validated (UNII)
Record Version
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Name Type Language
PIPERACILLIN SODIUM
EP   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
Piperacillin sodium [WHO-DD]
Common Name English
T-1220
Code English
Sodium (2S,5R,6R)-6-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Common Name English
PIPERACILLIN SODIUM [JAN]
Common Name English
PIPERACILLIN SODIUM [EP MONOGRAPH]
Common Name English
CL-227193
Code English
ZOSYN COMPONENT PIPERACILLIN SODIUM
Common Name English
PENMALIN
Brand Name English
PIPRACIL
Brand Name English
PIPERACILLIN SODIUM [USP MONOGRAPH]
Common Name English
PIPERACILLIN SODIUM [USAN]
Common Name English
PIPERACILLIN SODIUM COMPONENT OF ZOSYN
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((((4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL)AMINO)PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOSODIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))
Systematic Name English
PIPERACILLIN SODIUM SALT [MI]
Common Name English
NSC-757277
Code English
PIPERACILLIN SODIUM [VANDF]
Common Name English
PIPERACILLIN SODIUM SALT
MI  
Common Name English
PIPERACILLIN (AS SODIUM)
Common Name English
CL 227,193
Code English
PIPERACILLIN SODIUM [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1558
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
261-868-6
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
RXCUI
203134
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL702
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
PUBCHEM
23666879
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
NSC
757277
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
FDA UNII
M98T69Q7HP
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
EVMPD
SUB03840MIG
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
DRUG BANK
DBSALT001067
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
SMS_ID
100000089964
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
NCI_THESAURUS
C749
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
DAILYMED
M98T69Q7HP
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
CAS
59703-84-3
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
CHEBI
8233
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
MERCK INDEX
m8845
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6048965
Created by admin on Fri Dec 15 15:23:40 GMT 2023 , Edited by admin on Fri Dec 15 15:23:40 GMT 2023
PRIMARY
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