tazobactam (CHEBI:9421)

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ChEBI Name	tazobactam

ChEBI ID	CHEBI:9421

Definition	A member of the class of penicillanic acids that is sulbactam in which one of the exocyclic methyl hydrogens is replaced by a 1,2,3-triazol-1-yl group; used (in the form of its sodium salt) in combination with ceftolozane sulfate for treatment of complicated intra-abdominal infections and complicated urinary tract infections.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45973

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Formula

C10H12N4O5S

Net Charge

Average Mass

300.29100

Monoisotopic Mass

300.05284

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

InChIKey

LPQZKKCYTLCDGQ-WEDXCCLWSA-N

SMILES

C[C@]1(Cn2ccnn2)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic ) EC 3.5.2.6 (beta-lactamase) inhibitor An EC 3.5.2.* (non-peptide cyclic amide C-N hydrolase) inhibitor that interferes with the action of beta-lactamase (EC 3.5.2.6).

Application(s):	antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases.

ChEBI Ontology
Outgoing	tazobactam (CHEBI:9421) has functional parent sulbactam (CHEBI:9321) tazobactam (CHEBI:9421) has role antiinfective agent (CHEBI:35441) tazobactam (CHEBI:9421) has role antimicrobial agent (CHEBI:33281) tazobactam (CHEBI:9421) has role EC 3.5.2.6 (β-lactamase) inhibitor (CHEBI:35625) tazobactam (CHEBI:9421) is a penicillanic acids (CHEBI:25865) tazobactam (CHEBI:9421) is a triazoles (CHEBI:35727) tazobactam (CHEBI:9421) is conjugate acid of tazobactam(1−) (CHEBI:85193)

Incoming	tazobactam(1−) (CHEBI:85193) is conjugate base of tazobactam (CHEBI:9421)

IUPAC Name

(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-[(1H-1,2,3-triazol-1-yl)methyl]-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Synonym	Source
(2S,3S,5S)-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	ChemIDplus

Last Modified

22 February 2017