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	300.289 g/mol 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. In simple terms, it is an ingredient that can be added to certain antibiotics to make them less vulnerable to bacteria's antimicrobial resistance.

Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, used in infections due 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]

References

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.
Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.

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[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.

[2] Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.

Tazobactam

See also

References