Tazobactam

Tazobactam is a pharmaceutical drug that inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. It is commonly used as its sodium salt, tazobactam sodium. In simple terms, it is an ingredient that can be added to certain antibiotics to make them less vulnerable to bacteria's antimicrobial resistance.

Not to be confused with Teixobactin.
Tazobactam
Clinical data
AHFS/Drugs.comInternational Drug Names
License data
Pregnancy
category
  • B
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.108.321
Chemical and physical data
FormulaC10H12N4O5S
Molar mass300.29 g·mol−1
3D model (JSmol)
SMILES
  • O=S2(=O)[C@]([C@@H](N1C(=O)C[C@H]12)C(=O)O)(Cn3nncc3)C
InChI
  • InChI=1S/C10H12N4O5S/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)/t7-,8+,10+/m1/s1 Y
  • Key:LPQZKKCYTLCDGQ-WEDXCCLWSA-N Y
 NY (what is this?)  (verify)

Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, used in infections due to Pseudomonas aeruginosa. Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express β-lactamase and would normally degrade piperacillin.[1]

Tazobactam is a heavily modified penicillin and a sulfone.

Tazobactam was patented in 1982 and came into medical use in 1992.[2]

See also

References
  1. Yang Y, Rasmussen BA, Shlaes DM (1999). "Class A beta-lactamases—enzyme-inhibitor interactions and resistance". Pharmacol. Ther. 83 (2): 141–151. doi:10.1016/S0163-7258(99)00027-3. PMID 10511459.
  2. Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.


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