Tazobactam

Tazobactam

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	B
Routes of administration	Intravenous
Legal status
Legal status	℞ (Prescription only)
Identifiers
CAS Number	89786-04-9
ATC code	J01CG02 (WHO)
PubChem	CID 123630
DrugBank	DB01606
ChemSpider	110216
UNII	SE10G96M8W
KEGG	D00660
ChEBI	CHEBI:9421
ChEMBL	CHEMBL404
Chemical data
Formula	C10H12N4O5S
Molar mass	300.289 g/mol
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 Key:LPQZKKCYTLCDGQ-WEDXCCLWSA-N
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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.

Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, one of the preferred antibiotic treatments for nosocomial pneumonia caused by 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.

See also

• Ceftolozane
• Sulbactam

References

1. Yang Y, Rasmussen BA, Shlaes DM (1999). "Class A beta-lactamases—enzyme-inhibitor interactions and resistance". Pharmacol Ther. 83: 141–151. doi:10.1016/S0163-7258(99)00027-3.