89786-04-9 Usage
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.
Chemical Properties
White or off-white powder
Originator
CL-307579,China Pharm Chemical Co.,,China
Uses
Different sources of media describe the Uses of 89786-04-9 differently. You can refer to the following data:
1. b-lactamase inhibitor
2. Tazobactam is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.
Definition
ChEBI: 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 complicat
d intra-abdominal infections and complicated urinary tract infections.
Therapeutic Function
Antibiotic
Antimicrobial activity
Tazobactam exhibits little useful antimicrobial activity,
although weak activity against Acinetobacter spp. and Borrelia
burgdorferi has been reported.
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.
Veterinary Drugs and Treatments
Although veterinary experience is limited with piperacillin or piperacillin/
tazobactam, these drugs have expanded coverage against
many bacteria and may be suitable for empiric use until culture and
susceptibility data are available, or for surgical prophylaxis when
gram-negative or mixed aerobic/anaerobic infections are concerns.
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.
Metabolism
Piperacillin is metabolised to a minor microbiologically
active desethyl metabolite. Tazobactam is metabolised
to a single metabolite that has been found to be
microbiologically inactive.
Piperacillin and tazobactam are eliminated via the
kidney by glomerular filtration and tubular secretion.
Piperacillin, tazobactam, and desethyl piperacillin are also
secreted into the bile.
Check Digit Verification of cas no
The CAS Registry Mumber 89786-04-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,7,8 and 6 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 89786-04:
(7*8)+(6*9)+(5*7)+(4*8)+(3*6)+(2*0)+(1*4)=199
199 % 10 = 9
So 89786-04-9 is a valid CAS Registry Number.
InChI:InChI=1/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
89786-04-9Relevant articles and documents
Application of Continuous Flow in Tazobactam Synthesis
Sun, Tiemin,Wang, Jiasheng,Wu, Chengjun,Xin, Yunting,Zhou, Shuhao
, p. 1648 - 1657 (2021/07/19)
Tazobactam is a β-lactamase inhibitor. In this work, a combination of continuous flow and batch experiments for the synthesis of tazobactam has been developed. The first three steps and the preparation of the peroxyacetic acid are continuously carried out in the microreactors, which improves the procedure safety and efficiency. There is also a final step of the deprotection reaction in the microreactor, which can increase the yield and reduce the formation of impurities. Under optimized process conditions, the total yield of the target product reached 37.09% (30.93% in batch). The continuous flow method not only greatly reduces the reaction time but also significantly improves procedure safety and increases the yield.
2 β -triazole methylpenicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam
-
, (2021/11/21)
The invention provides a preparation method of 2 β -triazole methyl penicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: reacting a reaction raw material comprising a double-sulfur ring opening compound, 1, 2, 3 - triazole and first oxidizing agent in first solvent to obtain a product system comprising 2 β - triazole methylpenicillanic acid dibenzoate. The structural formula of 2 β -triazole methylpenicillanic acid dibenzoate is shown. Under the action first oxidizing agent 1, 2 and 3 - triazole are used for directly closing the bicyclic ring opening compound, and the efficient and high-selectivity synthesis of the bis-sulfur ring-opening compound directly to the key intermediate 2 β - triazole methylpenicillanic acid dibenzoate is successfully realized. Further, 2 β - triazole methyl penicillanic acid dibenzoate is used as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.
Synthesis method of tazobactam acid
-
, (2019/11/04)
The invention provides a synthesis method of tazobactam acid, and the method comprises the following steps: performing deamination reaction on 6-APA to obtain a compound A; selectively oxidizing the compound A by a Ce(OTf)4/H2O2 oxidation system to obtain a compound B; reacting the compound B with acetic anhydride to obtain a compound C; reacting the compound C with hydrazine hydrate to obtain a compound D; reacting the compound D with methanesulfonyl chloride to obtain a compound E, reacting the compound E with triazole to obtain a compound F, and performing oxidation reaction on the compoundF to obtain the tazobactam acid. The method has the advantages of simple operation steps, cheap and easily available reaction raw materials, short reaction steps, high purity of obtained intermediateproducts and products, purity of the final product tazobactam acid white solid powder of more than 99.5%, high total molar yield, suitability for industrial production, and wide application prospect.
