Compound ID | 1872

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Tazobactam

Synonym(s): YTR 830

Class: Beta-lactamase inhibitor

Agent Type: Semisynthetic; Small molecule; Direct acting; Antibiotic adjuvant;
Mechanism of action: Binds irreversibly to beta-lactamases, mainly class A enzymes
Combined with other compounds: Yes
Description: Semisynthetic, derived from sulbactam; only available as a combination product, multiple fixed combinations, parenteral application; penicillanic acid sulfone; no intrinsic antibacterial activity
Institute where first reported: Wyeth Pharmaceuticals
Year first mentioned: 1982
Highest development stage: Approved by FDA in 1993
Development status: Approved
Chemical structure(s):
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Molecular weight: 300.29
Iso. SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
InChI Key: LPQZKKCYTLCDGQ-WEDXCCLWSA-N
Can. SMILES: C[C@]1(CN2C=CN=N2)[C@H](C(=O)O)N3C(=O)C[C@H]3S1(=O)=O
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/123630
Guide to Pharmacology: tazobactam
Citations:
  • https://pubs.acs.org/doi/10.1021/acs.jmedchem.9b01279
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC179968/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2806661/
  • https://journals.asm.org/doi/epdf/10.1128/AAC.29.6.980

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