5935-65-9

Basic information

• Product Name: (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Des-acetyl Cephalothin;(6R)-3-(Hydroxymethyl)-8-oxo-7α-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(7R)-3-(Hydroxymethyl)-7β-(2-thienylacetylamino)cepham-3-ene-4-carboxylic acid;(7R)-3-(Hydroxymethyl)-7β-[(2-thienyl)acetylamino]cepham-3-ene-4-carboxylic acid;Cefalonium Impurity B;(7R)-3-(hydroxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefalotin Impurity B
• CAS NO: 5935-65-9
• Molecular Formula: C₁₄H₁₄N₂O₅S₂
• Molecular Weight: 354.40136
• EINECS: 227-690-8
• Mol File: 5935-65-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.8g/cm³
• Refractive Index: 1.729
• Storage Temp.: -20°C Freezer
• Solubility: Dioxane (Very Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(5935-65-9)
• EPA Substance Registry System: (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(5935-65-9)

Safety Data

• Hazardous Substances Data: 5935-65-9(Hazardous Substances Data)

Usage

Uses

Deacetylcephalothin (Cefalotin EP Impurity B) is an intermediate and the free acid analogue of Deacetylcephalothin Sodium Salt (D198210), which is an impurity in the synthesis of Cefalonium (C236800) and an analog of Cephalothin (C261150) a first-generation cephalosporin antibiotic used as a long-acting intramammary cerate for infusion of dairy cows.

InChI:InChI=1/C17H13IN2O4S/c1-2-23-11-5-3-10(4-6-11)20-16(22)13(15(21)19-17(20)25)9-12-7-8-14(18)24-12/h3-9H,2H2,1H3,(H,19,21,25)/b13-9+

Upstream product

• 58-71-9 sodium cephalothin 
• 957-68-6 7-Aminocephalosporanic acid 
• 19432-68-9 methyl 2-thiopheneacetate 
• 153-61-7 cephalothin 
• 39098-97-0 2-thienylacetic acid chloride 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Downstream Products

• 29126-13-4 3-hydroxymethyl-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 5575-21-3 (6R,7R)-3-[(4-formamido-1-pyridinyl)methyl]-8-oxo-7-[(2-acetylamino-2-yl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 10590-10-0 cefoxitin lactone 
• 135508-68-8 3-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 135508-69-9 (6R,7R)-8-Oxo-3-pentafluorophenyloxycarbonyloxymethyl-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 

Relevant articles and documents

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Progress towards a stable cephalosporin-halogenated phenazine conjugate for antibacterial prodrug applications

Resistant bacteria successfully evade the action of conventional antibiotic therapies during infection, often leading to significant illness and death. Our lab has discovered halogenated phenazine (HP) analogues which demonstrate potent antibacterial activities through a unique iron-starving mechanism. Herein, we describe synthetic efforts towards a stable cephalosporin-HP conjugate prodrug with the aim of translating HPs into useful clinical agents. Cephalosporin-antibiotic conjugates offer multiple advantages for antibacterial design, including the release of active agents through the targeting of intracellular cephalosporinase following selective ring-opening of the beta-lactam warhead. During these studies, carbonate-linked cephalosporin-HP conjugate 16 was synthesized; however, we were unable to successfully remove the ester group required for cephalosporinase processing. Cephalosporin-HP 16 was then utilized as a probe to investigate the stability of the carbonate linker in antibacterial assays and, as predicted, this compound proved to be inactive against Staphylococcus aureus (MIC > 100 μM). The lack of 16’s antibacterial activity can be attributed to the carbonate linker remaining intact throughout the MIC assay, thus not liberating the active HP moiety. These efforts have led to a more stable cephalosporin-HP conjugate joined through a carbonate linker compared to a highly unstable ether linked analogue we previously reported.

Synthesizing and purifying method of cefalonium

The invention discloses a synthesizing and purifying method of cefalonium and belongs to the technical field of medicine production. The method comprises a synthesizing step and a purifying step, wherein the synthesizing step comprises a synthesizing step of a cefalonium intermediate and a synthesizing step of a cefalonium coarse product. The method is characterized by comprising the step of obtaining a cefalonium fine product through the purifying step by means of the synthesizing step of the cefalonium intermediate and the synthesizing step of the cefalonium coarse product by taking D-7ACA as a raw material. The method disclosed by the invention has the beneficial effects that the process is slow in reaction and relatively high in safety; by introducing a catalyst, the reaction time is shortened greatly, and the production efficiency is increased; and the production cost is lowered greatly by successfully replacing 7-ACA by D-7ACA.