89786-04-9 Usage
Description
Tazobactam acid, a member of the penicillanic acid class, is a β-lactamase inhibitor with little or no antibacterial activity on its own. It is often coadministered with other β-lactam antibiotics, such as piperacillin, to enhance their effectiveness by inhibiting β-lactamases. Tazobactam is used in the form of its sodium salt and is characterized by its white or off-white powder appearance.
Uses
Used in Pharmaceutical Industry:
Tazobactam acid is used as a β-lactamase inhibitor for enhancing the effectiveness of β-lactam antibiotics. It is particularly used in combination with ceftolozane sulfate for the treatment of complicated intra-abdominal infections and complicated urinary tract infections. Its ability to inhibit β-lactamases allows for a more potent and targeted approach to treating bacterial infections, overcoming the resistance posed by these enzymes.
Originator
CL-307579,China Pharm Chemical Co.,,China
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
2 β - Azidomethyl penicillanic acid dibenzoate. Preparation method of tazobactam intermediate and tazobactam
-
, (2021/11/21)
The invention provides a preparation method of 2 β -azipenicillanic acid dibenzoate, tazobactam intermediate and tazobactam. The preparation method comprises the following steps: carrying out free radical reaction in a solvent by using a reaction raw material comprising a double-sulfur open-loop compound, a stacked nitrogen source and an oxidant to obtain a product system comprising 2 β - azidomethyl penicillanic acid dibenzoate. By radical addition of the carbon-carbon double bonds of the double-sulfur ring-opening compound through the azide free radical, high-efficiency and high-selectivity synthesis of the disulphide ring-opening compound directly to 2 β - azimaapenem naphthenate is successfully realized through intramolecular radical substitution. Further, 2 β - azidomethyl penicillanic acid dibenzoate is taken as a key intermediate for synthesizing tazobactam, the yield of tazobactam is improved, and the cost is reduced.
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.
