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Compound

Tazobactam

Also called Tazobactam acid

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Overview

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. WP

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] WP

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

Chemistry

Formula
C10H12N4O5S PC
CAS number
89786-04-9 PC
Molar mass (g/mol)
300.29 PC
IUPAC name (computed by PubChem)
(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid PC
SMILES
C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3 PC
InChIKey
LPQZKKCYTLCDGQ-WEDXCCLWSA-N PC
PubChem CID
123630
IUPAC name
(2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo WP

Harm reduction information

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Sources

  1. Journal / agency Yang Y, Rasmussen BA, Shlaes DM. Class A beta-lactamases--enzyme-inhibitor interactions and resistance. Pharmacology & Therapeutics. August 1999. doi:10.1016/S0163-7258(99)00027-3 · PMID 10511459
  2. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.