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

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11NO3S
Molecular Weight 201.243
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLANIC ACID

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)C(C)(C)S2

InChI

InChIKey=RBKMMJSQKNKNEV-RITPCOANSA-N
InChI=1S/C8H11NO3S/c1-8(2)6(7(11)12)9-4(10)3-5(9)13-8/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Rahnella aquatilis bacteremia in a patient with relapsed acute lymphoblastic leukemia.
2001
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
Renal abscess: recovery without hospitalization and drainage.
2001 Aug
Pharmacokinetic and pharmacodynamic profile of high dose extended interval piperacillin-tazobactam.
2001 Aug
Treatment of pulmonary nocardiosis in heart-transplant patients: importance of susceptibility studies.
2001 Dec
[Multicentre clinical trial on efficacy and safety of domestic piperacillin/tazobactam for treatment of acute bacterial infections].
2001 Jan 10
A randomized prospective multicentre trial of cefpirome versus piperacillin-tazobactam in febrile neutropenia.
2001 Jul
Piperacillin, beta-lactam inhibitor plus gentamicin as empirical therapy of a sequential regimen in febrile neutropenia of pediatric cancer patients.
2001 Jul
Inhibition of beta-lactamases by 6,6-bis(hydroxylmethyl)penicillanate.
2001 Jun
Molecular epidemiology of antibiotic-resistant gram-negative bacilli in a neonatal intensive care unit during a nonoutbreak period.
2001 Nov
The effect of a functional group in penicillin derivatives on the interaction with bile salt micelles studied by micellar electrokinetic chromatography.
2001 Oct
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
[Comparison of 2 administration protocols (continuous or discontinuous) of a time-dependent antibiotic, Tazocin].
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
[A multicenter clinical trial of piperacillin/tazobactam in burn infection].
2002 Apr
Synthesis of new C-6 alkyliden penicillin derivatives as beta-lactamase inhibitors.
2002 Apr
Clinical efficacy and pharmacoeconomics of a continuous-infusion piperacillin-tazobactam program in a large community teaching hospital.
2002 Apr
Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as beta-lactamase inhibitors.
2002 Aug
Selection of oxacillin resistance in oxacillin-sensitive Staphylococcus aureus through exposure to ciprofloxacin but not piperacillin/tazobactam.
2002 Aug
Lemierre's disease caused by co-infection of Arcanobacterium haemolyticum and Fusobacterium necrophorum: a case report.
2002 Aug
New and rapid fully automated method for determination of tazobactam and piperacillin in fatty tissue and serum by column-switching liquid chromatography.
2002 Aug 5
Postoperative infection with group A beta-hemolytic Streptococcus after blepharoplasty.
2002 Dec
[Study on water of crystallization in tazobactam].
2002 Feb
Penetration of piperacillin/tazobactam (4 g/500 mg) into synovial tissue.
2002 Feb
Comparison of aqueous and nonaqueous carrier electrolytes for the separation of penicillin V and related substances by capillary electrophoresis with UV and mass spectrometric detection.
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
Role of protein flexibility in enzymatic catalysis: quantum mechanical-molecular mechanical study of the deacylation reaction in class A beta-lactamases.
2002 Feb 27
Clinafloxacin versus piperacillin/tazobactam in the treatment of severe skin and soft-tissue infections in adults at a Veterans Affairs medical center.
2002 Jan
Infecting one animal with two different strains of the same bacteria may cause misleading results.
2002 Jul
Cefepime plus amikacin versus piperacillin-tazobactam plus amikacin for initial antibiotic therapy in haematology patients with febrile neutropenia: results of an open, randomized, multicentre trial.
2002 Jul
Role of alphaArg145 and betaArg263 in the active site of penicillin acylase of Escherichia coli.
2002 Jul 1
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.
2002 Jul 1
Ertapenem once daily versus piperacillin-tazobactam 4 times per day for treatment of complicated skin and skin-structure infections in adults: results of a prospective, randomized, double-blind multicenter study.
2002 Jun 1
[Piperacillin-tazobactam in the treatment of severe nosocomial infections].
2002 Mar
High-resolution X-ray structure of an acyl-enzyme species for the class D OXA-10 beta-lactamase.
2002 Mar 20
Potency and antimicrobial spectrum update for piperacillin/tazobactam (2000): emphasis on its activity against resistant organism populations and generally untested species causing community-acquired respiratory tract infections.
2002 May
Pharmacokinetic and pharmacodynamic evaluation of two dosing regimens for piperacillin-tazobactam.
2002 May
Comparative pharmacokinetic and pharmacodynamic profile of piperacillin/tazobactam 3.375G Q4H and 4.5G Q6H.
2002 May
Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors.
2002 Nov
Antimicrobial prophylaxis for transrectal prostatic biopsy: a prospective study of ciprofloxacin vs piperacillin/tazobactam.
2002 Nov
Factors governing intrinsic chemical reactivity differences between clavulanic and penicillanic acids.
2002 Oct 9
Efficacy and tolerability of prophylactic treatment with intravenous piperacillin/tazobactam in patients undergoing hematopoietic stem cell transplantation.
2002 Sep
Pharmacodynamic profiling of continuously infused piperacillin/tazobactam against Pseudomonas aeruginosa using Monte Carlo analysis.
2002 Sep
General microbiology and in vitro susceptibility of anaerobes isolated from complicated skin and skin-structure infections in patients enrolled in a comparative trial of ertapenem versus piperacillin-tazobactam.
2002 Sep 1
Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions.
2002 Sep 23
Mycotic aneurysm of the descending thoracic aorta caused by Pseudomonas aeruginosa in a solid organ transplant recipient: case report and review.
2002 Spring
Variable susceptibility to piperacillin/tazobactam amongst Klebsiella spp. with extended-spectrum beta-lactamases.
2003 Mar
Patents
Name Type Language
PENICILLANIC ACID
MI  
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-
Systematic Name English
PENICILLANIC ACID [MI]
Common Name English
(2S-CIS)-3,3-DIMETHYL-7-OXO-4-THIA-1- AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-, (2S,5R)-
Systematic Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3- DIMETHYL-7-OXO-, (2S-CIS)-
Systematic Name English
Code System Code Type Description
PUBCHEM
6891
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID90236038
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY
FDA UNII
PIS09H0QIX
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY
CAS
87-53-6
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-750-3
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY
MERCK INDEX
m8470
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY Merck Index
CHEBI
37806
Created by admin on Sat Dec 16 08:18:27 GMT 2023 , Edited by admin on Sat Dec 16 08:18:27 GMT 2023
PRIMARY