A β-lactamase inhibitor
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Alternative(s)
25679Tazobactam
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Tazobactam (sodium salt)

Item No. 17185

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4,4-dioxide 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, monosodium salt
CAS Number
89785-84-2
Synonyms
  • CL-307579
  • YTR 830
Molecular Formula
C10H11N4O5S • Na
Formula Weight
322.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
212 nm
SMILES
O=C(C1)N2[C@]1([H])S([C@](CN3C=CN=N3)(C)[C@@H]2C([O-])=O)(=O)=O.[Na+]
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Tazobactam is a β-lactamase inhibitor with greater activity against Ambler class A serine penicillinases and class C cephalosporinases, including TEM-1, SHV-1, and P99 (IC50s = 97, 150, and 8.5 nM) than class B metallo-β-lactamases and the class D oxacillinase OXA-1 (IC50s = 400,000 and 1,400 nM, respectively).1 However, it also inhibits the class D oxacillinase OXA-2 (IC50 = 10 nM). Tazobactam, in combination with piperacillin, is active against Gram-positive (MIC90s = 2-128 µg/ml) and Gram-negative bacteria (MIC90s = 4-128 µg/ml).2 In a neutropenic mouse model of thigh infection, tazobactam potentiates the activity of ceftolozane against Enterobacteriaceae.3 Formulations containing tazobactam, alone and in combination with piperacillin, have been used in the treatment of β-lacatamase-producing bacteria.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Drawz, S.M., and Bonomo, R.A. Three decades of β-lactamase inhibitors. Clin. Microbiol. Rev. 23(1), 160-201 (2010).

    2. Jones, R.N., Pfaller, M.A., Fuchs, P.C., et al. Piperacillin/tazobactam (YTR 830) combination. Comparative antimicrobial activity against 5889 recent aerobic clinical isolates and 60 Bacteroides fragilis group strains. Diagn. Microbiol. Infect. Dis. 12(6), 489-494 (1989).

    3. Craig, W.A., and Andes, D.R. In vivo activities of ceftolozane, a new cephalosporin, with and without tazobactam against Pseudomonas aeruginosa and Enterobacteriaceae, including strains with extended-spectrum β-lactamases, in the thighs of neutropenic mice. Antimicrob. Agents Chemother. 57(4), 1577-1582 (2013).