PIPERACILLIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H27N5O7S.H2O
Molecular Weight	535.57
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.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=NBXPLBPWMYNZTC-IDYPWDAWSA-N

InChI=1S/C23H27N5O7S.H2O/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);1H2/t13-,14-,15+,20-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 1A 45 Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Binding Agent 1076		940.0 nM [IC50]
Penicillin-binding protein 2B 10 Target ID: P0A3M6 Gene ID: 933948.0 Gene Symbol: penA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Binding Agent 1076		51.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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
Skin and skin structure infections 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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
Female pelvic infections 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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
Community-acquired pneumonia 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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
Nosocomial pneumonia 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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

C_max

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

T_1/2

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
4 g 4 times / day multiple, intravenous Dose: 4 g, 4 times / day Route: intravenous Route: multiple Dose: 4 g, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050545s053lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438 inducer 440

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A5 136 CYP2C8 1057 OAT1 725 OAT3 747	OAT1 395 OAT3 391	CYP3A5 92 P-gp 301

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A5 201	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
CYP3A5 201	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	no
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/11850258/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26763401/	weak [IC50 1140 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32104494/	yes
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/32104494/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes [Km 172 uM]
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes [Km 37 uM]

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01410	http://www.3bsc.com/index/pro_info.php?id=21622
3B Scientific (Wuhan) Corp	3B2-1697	http://www.3bsc.com/index/pro_info.php?id=56231
abcr GmbH	AB479648	http://www.abcr.com/shop/en/AB479648
Achemtek	0102-022374	http://www.achemtek.com/61477-96-1
AHH Chemical co.,ltd	MT-58012	http://www.ahhchemical.com/product/MT-58012.html
AHH Chemical co.,ltd	MT-58917	http://www.ahhchemical.com/product/MT-58917.html
AK Scientific, Inc. (AKSCI)	J10085	http://www.aksci.com/item_detail.php?cat=J10085
Angene	AGN-PC-0T0LDB	http://www.angenechemical.com/productshow/AGN-PC-0T0LDB.html
Aurora Fine Chemicals LLC	A13.110.313	http://online.aurorafinechemicals.com/info?ID=A13.110.313
Aurum Pharmatech LLC	KM0517	http://www.Aurumpharmatech.com/Product/ProductDetails/KM0517
AvaChem Scientific	4535	http://www.avachem.com/productSearch.asp?4535
BioSynth	W-105153	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/W-105153.html
BLD Pharm	BD239259	http://www.bldpharm.com/products/61477-96-1.html
ChemMol	49424430	http://www.chemmol.com/chemmol/49424430.html
ChemMol	99119834	http://www.chemmol.com/chemmol/99119834.html
Chemspace	CSSB00016990198	https://chem-space.com/CSSB00016990198
Clearsynth	CS-O-14488	https://www.clearsynth.com/en/CSO14488.html
Glentham Life Sciences	GA9881	http://www.glentham.com/products/product/GA9881/
Hairui	HR134010	http://www.hairuichem.com/en/product/61477-96-1.html
iChemical	EBD29493	http://www.ichemical.com/chemicals/cas-61477-96-1
Lab Network	LN00199061	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00199061
LGC Standards	DRE-C16218900	https://www.lgcstandards.com/US/en/p/DRE-C16218900
LGC Standards	LGCFOR0295.00	https://www.lgcstandards.com/US/en/p/LGCFOR0295.00
LGC Standards	MM0295.00	https://www.lgcstandards.com/US/en/p/MM0295.00
Matrix Scientific	97252	https://www.matrixscientific.com/097252.html
MuseChem	R011373	https://www.musechem.com/product/R011373.html
OChem	6047	http://www.ocheminc.com/index.php?act=psearch&pid=477P961
Parchem	44935	https://www.parchem.com/chemical-supplier-distributor/Pipracil-044935.aspx
Smolecule	S589373	https://www.smolecule.com/products/s589373
THE BioTek	bt-505814	https://www.thebiotek.com/product/others/bt-505814
Yuhao Chemical	RT10348	http://www.chemyuhao.com/61477-96-1.html

PubMed

Title	Date	PubMed
Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936).	2002-03	11864948
Multidrug-resistant Pseudomonas aeruginosa bloodstream infections: analysis of trends in prevalence and epidemiology.	2002-02	11897080
Antibiotic resistance patterns of bacterial isolates from blood in San Francisco County, California, 1996-1999.	2002-02	11897073
Penetration of piperacillin/tazobactam (4 g/500 mg) into synovial tissue.	2002-02	11892900
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.	2002-02	11850161
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.	2002-02	11815589
Multicentre evaluation of the VITEK 2 Advanced Expert System for interpretive reading of antimicrobial resistance tests.	2002-02	11815570
CAPD-associated peritonitis caused by Alcaligenes xylosoxidans sp. xylosoxidans.	2002-01-19	11799270
Distribution and prevalence of antimicrobial resistance among gram-negative isolates in intensive care units (ICU) in Belgian hospitals between 1996 and 1999.	2002-01-05	11770225
Clinafloxacin versus piperacillin/tazobactam in the treatment of severe skin and soft-tissue infections in adults at a Veterans Affairs medical center.	2002-01	11833836
In vitro synergy testing of levofloxacin, ofloxacin, and ciprofloxacin in combination with aztreonam, ceftazidime, or piperacillin against Pseudomonas aeruginosa.	2002-01	11821176
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.	2002-01	11821175
Antibiotic-induced recurring interstitial nephritis.	2002-01	11793135
Effect of piperacillin-tazobactam on clinical capillary zone electrophoresis of serum proteins.	2002-01	11751563
Surveillance for antimicrobial resistance in Croatia.	2002-01	11749742
Nosocomial pneumonia in pediatric patients: practical problems and rational solutions.	2002	11888355
Influence of previous exposure to antibiotic therapy on the susceptibility pattern of Pseudomonas aeruginosa bacteremic isolates.	2001-12-01	11692297
Antimicrobial susceptibility of respiratory isolates of Enterobacteriaceae and Staphylococcus aureus in Italy: incidence and trends over the period 1997-1999.	2001-12	11837636
Survey of antibiotic resistance in Pseudomonas aeruginosa by The Tokyo Johoku Association of Pseudomonas Studies.	2001-12	11810595
[Interventional ERCP in patients with cholestasis. Degree of biliary bacterial colonization and antibiotic resistance].	2001-12	11753782
Treatment of pulmonary nocardiosis in heart-transplant patients: importance of susceptibility studies.	2001-12	11737119
Elimination of the piperacillin/tazobactam combination during continuous venovenous haemofiltration and haemodiafiltration in patients with acute renal failure.	2001-12	11733473
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001-11	11792017
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!	2001-11	11750171
Hand infections in patients with diabetes mellitus.	2001-11	11727802
Stability of piperacillin and ticarcillin in AutoDose infusion system bags.	2001-11	11724082
Molecular epidemiology of antibiotic-resistant gram-negative bacilli in a neonatal intensive care unit during a nonoutbreak period.	2001-11	11694694
In vitro antimicrobial susceptibility of Aerococcus urinae to 14 antibiotics, and time-kill curves for penicillin, gentamicin and vancomycin.	2001-11	11679554
A multicenter, double-blind, placebo-controlled trial comparing piperacillin-tazobactam with and without amikacin as empiric therapy for febrile neutropenia.	2001-10-15	11565068
Immediate remission obtained by minocycline in a patient with histiocytic necrotizing lymphadenitis.	2001-10	11688834
Postantibiotic effects of eleven antimicrobials on five bacteria.	2001-09	11749860
Piperacillin/Tazobactam versus cefotaxime plus metronidazole for treatment of children with intra-abdominal infections requiring surgery.	2001-09	11714046
Isolation and culture of airway epithelial cells from chronically infected human lungs.	2001-09	11669281
[Comparison of 2 administration protocols (continuous or discontinuous) of a time-dependent antibiotic, Tazocin].	2001-09	11642016
[Survey of the antibiotic sensitivity of Pseudomonas aeruginosa in France and the distribution of beta-lactam resistance mechanisms: the GERPB 1999 study].	2001-09	11642015
Evaluating possible pharmacokinetic interactions between tobramycin, piperacillin, and a combination of piperacillin and tazobactam in patients with various degrees of renal impairment.	2001-09	11549103
Effect of mono-dose intraperitoneal cecropins in experimental septic shock.	2001-09	11546961
Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting.	2001-09	11533004
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.	2001-08	11589485
[Antimicrobial activities and mechanisms of carbapenem resistance in clinical isolates of carbapenem-resistant Pseudomonas aeruginosa and Acinetobacter spp].	2001-08	11558128
Prevalence and analysis of risk factors for infections caused by resistant Escherichia coli strains in Anhui, China.	2001-08	11545486
A randomized prospective multicentre trial of cefpirome versus piperacillin-tazobactam in febrile neutropenia.	2001-07	11699402
[Analysis of the risk factors and drug resistance of lower respiratory tract infection by Flavobacteria].	2001-06	11802986
[Mycoplasma pneumonia complicated by acute renal failure].	2001-06	11530392
Infections caused by Flavimonas oryzihabitans.	2001-04	11780462
[Multicentre clinical trial on efficacy and safety of domestic piperacillin/tazobactam for treatment of acute bacterial infections].	2001-01-10	11798851
[Surveillance of bacterial resistance in Shanghai].	2001-01-10	11798844
Peritonitis in automated peritoneal dialysis: antibiotic therapy and pharmacokinetics.	2001	11887820
[Use of the Etest method for antimicrobial susceptibility testing of obligate anaerobes].	2001	11757426
Piperacillin/tazobactam: a pharmacoeconomic review of its use in moderate to severe bacterial infections.	2001	11735679

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 17:52:09 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:09 GMT 2025`
Record UNII	X00B0D5O0E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIPERACILLIN HYDRATE

Preferred Name

English

PIPERACILLIN

Official Name

English

PIPERACILLIN HYDRATE [JAN]

Common Name

English

PIPERACILLIN MONOHYDRATE [EP MONOGRAPH]

Common Name

English

PIPERACILLIN [VANDF]

Common Name

English

PIPERACILLIN [USP MONOGRAPH]

Common Name

English

PIPERACILLIN MONOHYDRATE

Official Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-(((4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL)AMINO)PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOHYDRATE, (2S,5R,6R)-

Common Name

English

Piperacillin monohydrate [WHO-DD]

Common Name

English

(2S,5R,6R)-6-(((2R)-2-(((4-ETHYL-2,3-DIOXOPIPERAZIN-1-YL)CARBONYL)AMINO)-2-PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID HYDRATE

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175497