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T2820

Sigma-Aldrich

Tazobactam sodium salt

β-lactamase inhibitor

Synonym(s):

CL-298741, YTR-830H, [2S-(2α, 3β, 5α)]-3-Methyl-7-oxo-3(1H,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide

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About This Item

Empirical Formula (Hill Notation):
C10H11N4NaO5S
CAS Number:
89785-84-2
Molecular Weight:
322.27
MDL number:
MFCD00917472
UNSPSC Code:
51101500
PubChem Substance ID:
329826726
NACRES:
NA.85

Quality Level

100

form

powder or crystals

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

cell wall synthesis | interferes

SMILES string

[Na+].C[C@]2(Cn1ccnn1)[C@@H](N3[C@@H](CC3=O)S2(=O)=O)C([O-])=O

InChI

1S/C10H12N4O5S.Na/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h2-3,7-8H,4-5H2,1H3,(H,16,17);/q;+1/p-1/t7-,8+,10+;/m1./s1

InChI key

RFMIKMMOLPNEDG-QVUDESDKSA-M

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General description

Chemical structure: ß-lactam

Application

Tazobactam is an antibacterial penicillin derivative which inhibits the action of bacterial β-lactamases. It is used in combination with piperacillin and other β-lactam antibiotics to broaden their spectrum and enhance their effect. It is used for bacterial β-lactamase and penicillinase inhibition studies.

Biochem/physiol Actions

Tazobactam is a β -Lactamase inhibitor. When used with β-lactam antibiotics I, it enhances their effect.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro antimicrobial activity of piperacillin/tazobactam in comparison with other broad-spectrum β-lactams. .
Roland, R. K., et al.
The Journal of Infectious Diseases, 4, 226-226 (2000)
R A Bonomo et al.
Biochimica et biophysica acta, 1547(2), 196-205 (2001-06-19)
The CMY-2 beta-lactamase, a plasmid determined class C cephalosporinase, was shown to be susceptible to inhibition by tazobactam (K(i)=40 microM). The reaction product(s) of CMY-2 beta-lactamase with the beta-lactamase inhibitor tazobactam were analyzed by electrospray ionization/mass spectrometry (ESI/MS) to characterize
Gioia S Babini et al.
The Journal of antimicrobial chemotherapy, 51(3), 605-612 (2003-03-05)
MICs of piperacillin/tazobactam are conventionally determined by varying the concentration of piperacillin in the presence of a fixed 4 mg/L tazobactam. When tested in this way, the MIC distribution for Klebsiella isolates with extended-spectrum beta-lactamases (ESBLs) is strongly bimodal, such
Craig Knox et al.
Nucleic acids research, 39(Database issue), D1035-D1041 (2010-11-10)
DrugBank (http://www.drugbank.ca) is a richly annotated database of drug and drug target information. It contains extensive data on the nomenclature, ontology, chemistry, structure, function, action, pharmacology, pharmacokinetics, metabolism and pharmaceutical properties of both small molecule and large molecule (biotech) drugs.
Johannes Zander et al.
Clinical chemistry and laboratory medicine, 53(5), 781-791 (2014-10-11)
Recent studies have demonstrated highly variable blood concentrations of piperacillin, tazobactam, cefepime, meropenem, ciprofloxacin and linezolid in critically ill patients with a high incidence of sub-therapeutic levels. Consequently, therapeutic drug monitoring (TDM) of these antibiotics has to be considered, requiring

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