76610-84-9

Basic information

• Product Name: Cefbuperazone
• Synonyms: 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((2-(((4-ethyl-2,3-dio;methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-,(6r-(6-alpha,7-alpha,7(2r*,3s*));xo-1-piperazinyl)carbonyl)amino)-3-hydroxy-1-oxobutyl)amino)-7-methoxy-3-(((1-;CEFBUPERAZONE;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R,3S)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-3-hydroxy-1-oxobutyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7S)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-3-hydroxy-1-oxobutyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6α,7α,7(2R*,3S*)]]-;(6R,7S)-7-((2R,3S)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Keiperazon
• CAS NO: 76610-84-9
• Molecular Formula: C22H29N9O9S2
• Molecular Weight: 627.65
• EINECS: 1308068-626-2
• Mol File: 76610-84-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 118-120° (dec)
• Appearance: /
• Density: 1.772 g/cm³
• Refractive Index: 1.778
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Hygroscopic
• CAS DataBase Reference: Cefbuperazone(CAS DataBase Reference)
• NIST Chemistry Reference: Cefbuperazone(76610-84-9)
• EPA Substance Registry System: Cefbuperazone(76610-84-9)

Safety Data

• Hazardous Substances Data: 76610-84-9(Hazardous Substances Data)

Usage

Description

Cefbuperazone, a second-generation cephalosporin antibiotic, is a semi-synthetic β-lactam antibiotic derived from the cephalosporin class. It is characterized by the presence of [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and N-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-D-threonylamino side groups at positions 3 and 7β, respectively. As a peptide and cephalosporin, Cefbuperazone exhibits broad-spectrum antimicrobial activity, making it a valuable pharmaceutical agent in treating various infections.

Uses

Used in Pharmaceutical Industry:
Cefbuperazone is used as a broad-spectrum antibiotic for the treatment of a wide range of bacterial infections. Its effectiveness against both Gram-positive and Gram-negative bacteria, including some antibiotic-resistant strains, makes it a crucial component in the management of various infections.
Used in Hospital Settings:
In hospitals, Cefbuperazone is utilized as an antibiotic for the treatment of severe infections, such as pneumonia, urinary tract infections, skin and soft tissue infections, and bone and joint infections. Its broad-spectrum activity allows for effective treatment of infections caused by multiple bacterial species.
Used in Community-Acquired Infections:
Cefbuperazone is also used in the treatment of community-acquired infections, such as respiratory tract infections, including bronchitis and pneumonia, as well as skin and soft tissue infections. Its broad-spectrum coverage makes it a suitable choice for empiric therapy when the causative pathogen is unknown.
Used in Combination Therapy:
In some cases, Cefbuperazone may be used in combination with other antibiotics to enhance the treatment of complex or resistant infections. This combination therapy can help to broaden the antimicrobial spectrum and improve the overall effectiveness of the treatment.
Overall, Cefbuperazone's versatility and broad-spectrum activity make it an essential antibiotic in the pharmaceutical industry for the treatment of various bacterial infections across different settings.

Antimicrobial activity

Cefbuperazone is a semisynthetic cephamycin antibiotic with properties similar to those of cefoxitin, but somewhat more active against B. fragilis and enterobacteria. It is not hydrolyzed by common β-lactamases and as a result its activity is not affected by inoculum size. It is not active against cefoxitin-resistant strains. It is available in Japan.

InChI:InChI=1/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1

Relevant articles and documents

Synthesis method of cefbuperazone

The invention discloses a synthesis method of cefbuperazone. The synthesis method comprises the following steps: (1) synthesizing an intermediate I, (2) carrying out an acylation reaction process, (3)removing a protecting group, (4) purifying an intermediate III, and (5) carrying out alcoholysis and purification treatment. According to the synthesis method of cefbuperazone, through scientific rawmaterial selection and design of synthesis process conditions, triethylamine is adopted as an acid-binding agent, so that the reaction stability is effectively improved, and the generation of byproducts is reduced; the m-cresol is adopted to carry out the reaction of removing the diphenyl methyl protecting group, so that the quality and the yield of the product are effectively improved; the synthesis method is stable in reaction process, safe, controllable, good in product quality, high in yield and suitable for industrial mass production.