Tazobactam

Tazobactam
Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by INN;
Pregnancy; category	B;
Routes of; administration	Intravenous
ATC code	J01CG02 (WHO) ;
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	89786-04-9 ;
PubChem CID	123630;
DrugBank	DB01606 ;
ChemSpider	110216 ;
UNII	SE10G96M8W;
KEGG	D00660 ;
ChEBI	CHEBI:9421 ;
ChEMBL	ChEMBL404 ;
CompTox Dashboard (EPA)	DTXSID8023634 ;
ECHA InfoCard	100.108.321
Chemical and physical data
Formula	C10H12N4O5S
Molar mass	300.29 g·mol−1
3D model (JSmol)	Interactive image;
	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, 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 was patented in 1982 and came into medical use in 1992.^[2]

References

^ Yang Y, Rasmussen BA, Shlaes DM (August 1999). "Class A beta-lactamases--enzyme-inhibitor interactions and resistance". Pharmacology & Therapeutics. 83 (2): 141–151. doi:10.1016/S0163-7258(99)00027-3. PMID 10511459.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.