TAZ

TAZOBACTAM

Created:2000-11-21
Last modified:  2025-04-30

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Chemical Details

Formal Charge0
Atom Count32
Chiral Atom Count3
Bond Count34
Aromatic Bond Count5
2D diagram of TAZ

Chemical Component Summary

NameTAZOBACTAM
Systematic Name (OpenEye OEToolkits)(2~{S},3~{S},5~{R})-3-methyl-4,4,7-tris(oxidanylidene)-3-(1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC10 H12 N4 O5 S
Molecular Weight300.291
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs14.52O=S1(=O)C2CC(=O)N2C(C(=O)O)C1(C)Cn1ccnn1
SMILESCACTVS3.385C[C]1(Cn2ccnn2)[CH](N3[CH](CC3=O)[S]1(=O)=O)C(O)=O
SMILESOpenEye OEToolkits3.1.0.0CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)Cn3ccnn3
Canonical SMILESCACTVS3.385 C[C@]1(Cn2ccnn2)[C@@H](N3[C@@H](CC3=O)[S]1(=O)=O)C(O)=O
Canonical SMILESOpenEye OEToolkits3.1.0.0 C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)Cn3ccnn3
InChIInChI1.06 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
InChIKeyInChI1.06 LPQZKKCYTLCDGQ-WEDXCCLWSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB01606 
NameTazobactam
Groups approved
DescriptionTazobactam is an antibiotic of the beta-lactamase inhibitor class that prevents the breakdown of other antibiotics by beta-lactamase enzyme producing organisms. It is combined with [Piperacillin] and [Ceftolozane] for the treatment of a variety of bacterial infections. Piperacillin-tazobactam was initially approved by the FDA in 1994, and ceftolozane-tazobactam was approved by the FDA in 2014[FDA label], providing wider antibacterial coverage for gram-negative infections. In June 2019, ceftolozane-tazobactam was approved by the FDA for treating hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia, which are significant causes of morbidity and mortality in hospitalized patients.[L6673]
Synonyms
  • Tazobactam
  • Tazobactamum
  • Tazobactam sodium
Brand Names
  • Piperacillin Sodium / Tazobactam Sodium
  • PIPERACILLIN SODIUM and TAZOBACTAM SODIUM
  • Zerbaxa
  • Zosyn
  • Zosyn in Galaxy Containers
IndicationTazobactam is used in combination with piperacillin or ceftolozane to broaden the spectrum of piperacillin antibacterial action, treating susceptible infections. As with any other antibiotic, tazobactam should only be used for infections that are either proven or strongly suspected to be susceptible to the tazobactam containing drug. **Tazobactam-piperacillin** When combined with piperacillin, it is used to treat a variety of infections, including those caused by aerobic and facultative gram-positive and gram-negative bacteria, in addition to gram-positive and gram-negative anaerobes. Some examples of infections treated with piperacillin-tazobactam include cellulitis, diabetic foot infections, appendicitis, and postpartum endometritis infections.[L4417] Certain gram-negative bacilli infections with beta-lactamase producing organisms cannot be treated with piperacillin-tazobactam, due to a gene mutation conferring antibiotic resistance.[A179266] **Tazobactam-ceftolozane** Tazobactam is used in combination with [ceftolozane] for the treatment of infections caused by designated susceptible microorganisms in adult and pediatric patients:[L41618] - Complicated Intra-abdominal Infections (cIAI), used in combination with [metronidazole] - Complicated Urinary Tract Infections (cUTI), including pyelonephritis - Hospital-acquired Bacterial Pneumonia and Ventilator-associated Bacterial Pneumonia (HABP/VABP)
Categories
  • Amides
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
  • Aza Compounds
ATC-CodeJ01CG02
CAS number89786-04-9

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Beta-lactamaseMKKLIFLIVIALVLSACNSNSSHAKELNDLEKKYNAHIGVYALDTKSGKE...unknowninhibitor
Beta-lactamase TEMMSIQHFRVALIPFFAAFCLPVFAHPETLVKVKDAEDQLGARVGYIELDLN...unknowninhibitor
Beta-lactamase Ohio-1MRYFRLCIISLLATLPLRVHAGPQPLEQIKLSESQLSGSVGMIEMDLARP...unknowninhibitor
Beta-lactamase SHV-1MRYIRLCIISLLATLPLAVHASPQPLEQIKLSESQLSGRVGMIEMDLASG...unknowninhibitor
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 17754193