Tazobactam acid
[CAS# 89786-04-9]

Identification

• Classification: API >> Antibiotics >> Beta-lactamase inhibitor
• Name: Tazobactam acid
• Synonyms: (2S,3S,5R)-3-Methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Molecular Formula: C₁₀H₁₂N₄O₅S
• Molecular Weight: 300.29
• CAS Registry Number: 89786-04-9
• EC Number: 618-303-7
• SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3

Properties

• Solubility: 10 mM (DMSO) (Expl.)
• Density: 1.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.818, Calc.^*
• Boiling Point: 707.1±70.0 °C (760 mmHg), Calc.^*
• Flash Point: 381.4±35.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Dander
• Risk Statements: H317-H334-H373-H400-H411
• Safety Statements: P233-P260-P261-P271-P272-P273-P280-P284-P302+P352-P304+P340-P319-P321-P333+P317-P342+P316-P362+P364-P391-P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Respiratory sensitization	Resp. Sens.	1	H334
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Tazobactam acid is a chemical compound used primarily in the treatment of bacterial infections. It is a beta-lactamase inhibitor that is often combined with antibiotics such as piperacillin to combat infections caused by antibiotic-resistant bacteria. The discovery of tazobactam can be traced back to the 1980s, when it was developed as part of efforts to counter the increasing threat of bacterial resistance to beta-lactam antibiotics.

Tazobactam acid works by inhibiting beta-lactamase enzymes, which are produced by certain bacteria to degrade beta-lactam antibiotics like penicillins and cephalosporins. By inhibiting these enzymes, tazobactam enhances the effectiveness of the co-administered antibiotics, allowing them to work more effectively against resistant strains. This mechanism of action has made tazobactam a valuable component in the treatment of infections caused by resistant pathogens, including Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae.

The combination of tazobactam with piperacillin is marketed under the brand name Zosyn, and it is widely used in hospitals to treat a variety of infections, including pneumonia, intra-abdominal infections, and urinary tract infections. The effectiveness of this combination therapy has made it a standard treatment option for patients with severe infections caused by resistant organisms. Tazobactam acid itself is not used as a standalone antibiotic, as its primary role is to enhance the activity of piperacillin.

In addition to its clinical uses, research into the development of newer beta-lactamase inhibitors, such as tazobactam, continues. These inhibitors play a critical role in combating the growing issue of antimicrobial resistance, and innovations in this area are essential for developing new therapies to treat difficult-to-treat infections.

Tazobactam acid’s role in modern medicine highlights the importance of combating bacterial resistance, which remains one of the most significant challenges in infectious disease treatment. With ongoing advancements in research, the use of tazobactam and similar compounds will continue to evolve, offering hope for more effective treatments for resistant infections.

References

2007. Biochemical Characterization of PER-2 and Genetic Environment of bla PER-2. Antimicrobial Agents and Chemotherapy, 51(7).
DOI: 10.1128/aac.01395-06

2005. Quantitation and stability of piperacillin and tazobactam in plasma and ultrafiltrate from patients undergoing continuous venovenous hemofiltration by HPLC. Biomedical chromatography : BMC, 19(4).
DOI: 10.1002/bmc.482

2003. Piperacillin-tazobactam is more effective than ceftriaxone plus gentamicin in febrile neutropenic patients with hematological malignancies: a randomized comparison. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer, 11(6).
DOI: 10.1007/s00520-003-0463-7