CHEBI:9421 - tazobactam

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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 0
Average Mass 300.29100
Monoisotopic Mass 300.053
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.
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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]-6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
INNs Sources
tazobactam ChemIDplus
tazobactamum ChemIDplus
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
Manual Xrefs Databases
2572 DrugCentral
C07771 KEGG COMPOUND
D00660 KEGG DRUG
DB01606 DrugBank
LSM-5323 LINCS
TAZ PDBeChem
Tazobactam Wikipedia
View more database links
Registry Numbers Types Sources
4787944 Reaxys Registry Number Reaxys
89786-04-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
25098503 PubMed citation Europe PMC
25512410 PubMed citation Europe PMC
25529765 PubMed citation Europe PMC
25609660 PubMed citation Europe PMC
25662788 PubMed citation Europe PMC
25670823 PubMed citation Europe PMC
Last Modified
22 February 2017