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

Uses

Cefbuperazone is a second-generation cephalosporin antibiotic.

Definition

ChEBI: Cefbuperazone is a second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and {N-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-D-threonyl}amino side groups located at positions 3 and 7beta respectively. It is a peptide and a cephalosporin.

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.