Tazobactam

Base Information

• Chemical Name: Tazobactam
• CAS No.: 89786-04-9
• Molecular Formula: C10H12N4O5S
• Molecular Weight: 300.295
• Hs Code.: 2941106000
• European Community (EC) Number: 618-303-7
• UNII: SE10G96M8W
• DSSTox Substance ID: DTXSID8023634
• Nikkaji Number: J246.119F
• Wikipedia: Tazobactam
• Wikidata: Q423376
• NCI Thesaurus Code: C62079
• RXCUI: 37617
• Metabolomics Workbench ID: 43592
• ChEMBL ID: CHEMBL404
• Mol file: 89786-04-9.mol

Synonyms:tazobactam;Tazobactam Sodium;YTR 830;YTR 830H;YTR-830;YTR830

Chemical Property of Tazobactam

Chemical Property:

• Appearance/Colour: White or off-white powder
• Vapor Pressure: 5.55E-21mmHg at 25°C
• Melting Point: 115-145℃
• Refractive Index: 1.817
• Boiling Point: 707.1 °C at 760 mmHg
• PKA: 2.33±0.40(Predicted)
• Flash Point: 381.4 °C
• PSA: 127.43000
• Density: 1.92 g/cm³
• LogP: -0.40470
• Storage Temp.: Store at?0-5°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
• Water Solubility.: Soluble in water
• XLogP3: -2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 300.05284067
• Heavy Atom Count: 20
• Complexity: 573

Purity/Quality:

98%min ^*data from raw suppliers

Tazobactam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
• Isomeric SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
• Recent ClinicalTrials: Comparative Study To Determine The Efficacy, Safety, And Tolerability Of Ceftolozane-Tazobactam
• Recent EU Clinical Trials: Efficacy of extended infusion of β-lactam antibiotics for the treatment of febrile neutropenia in hematologic patients (BEATLE study).
• Description: Tazobactam often is coadministered with piperacillin because of tazobactam's ability to inhibit β-lactamases. T azobactam, like other β-lactamase inhibitors, has little or no antibacterial activity. This effect is analogous to that of clavulanic acid and sulbactam.
• Uses: b-lactamase inhibitor Tazobactam is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.
• Therapeutic Function: Antibiotic
• Clinical Use: Tazobactam is a penicillanic acid sulfone that is similar instructure to sulbactam. It is a more potent β-lactamaseinhibitor than sulbactam and has a slightly broader spectrumof activity than clavulanic acid. It has very weak antibacterialactivity. Tazobactam is available in fixed-dose, injectablecombinations with piperacillin, a broad-spectrum penicillinconsisting of an 8:1 ratio of piperacillin sodium to tazobactamsodium by weight and marketed under the trade name Zosyn.The pharmacokinetics of the two drugs are very similar. Bothhave short half-lives (t1/2 ～1 hour), are minimally proteinbound, experience very little metabolism, and are excreted inactive forms in the urine in high concentrations.Approved indications for the piperacillin–tazobactamcombination include the treatment of appendicitis, postpartumendometritis, and pelvic inflammatory disease caused byβ-lactamase–producing E. coli and Bacteroides spp., skin andskin structure infections caused by β-lactamase–producingS. aureus, and pneumonia caused by β-lactamase–producingstrains of H. influenzae.
• Drug interactions: Potentially hazardous interactions with other drugs Reduced excretion of methotrexate - monitor methotrexate levels during concomitant treatment. Enhanced action of vecuronium and similar neuromuscular blocking agents.

Technology Process of Tazobactam

There total 53 articles about Tazobactam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.19%

tazobactam benzyl ester → tazobactam acid (89786-04-9,115546-66-2,124995-08-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; for 1.5h; under 375.038 Torr;

Reference yield: 94.2%

tazobactam 3,5-dinitrobenzyl ester → tazobactam acid (89786-04-9,115546-66-2,124995-08-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In dichloromethane; at 20 - 30 ℃; Temperature;

Reference yield: 94.1%

(2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester (89789-07-1) → tazobactam acid (89786-04-9,115546-66-2,124995-08-0)

Guidance literature:

With 3-methyl-phenol; at 50 ℃; for 4h;

upstream raw materials:

6-bromopenicillanic acid

6-Aminopenicillanic Acid

2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester

Downstream raw materials:

sodium piperacillin

tazobactam sodium

Refernces

• 1、 -. "2 β -triazole methylpenicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam". Paragraph 0058; 0063-0108; 0108; 0111-0115. . Retrieved 2021/11/21.
• 2、 -. "Tazobactam intermediate, preparation method thereof and method for preparing tazobactam by using intermediate (by machine translation)". Paragraph 0097-0102. . Retrieved 2020/11/23.