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cefaloglycin

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cefaloglycin Basic information
cefaloglycin Chemical Properties
  • Melting point:236.5°C (rough estimate)
  • Boiling point:217.4°C (rough estimate)
  • Density 1.3328 (rough estimate)
  • refractive index 1.6390 (estimate)
  • storage temp. 2-8°C
  • pkapKa 1.71(H2O t=25±2 I=0.1 ) (Uncertain);7.29(H2O t=25±2 I=0.1 ) (Uncertain)
  • Water Solubility 10.5g/L(25 ºC)
Safety Information
cefaloglycin Usage And Synthesis
  • OriginatorKefglycin,Shionogi,Japan,1969
  • UsesCefaloglycin is a first-generation cephalosporin antibiotic.
  • UsesAntibacterial.
  • DefinitionChEBI: A cephalosporin antibiotic containing at the 7beta-position of the cephem skeleton an (R)-amino(phenyl)acetamido group.
  • Manufacturing Processdl-Phenylglycine is resolved in a conventional manner by reaction with cinchonine, fractional crystallization of the resulting diastereoisomers, and acidification to release the phenylglycine enantiomorphs. D-phenylglycine, thus prepared, is reacted with carbobenzoxy chloride in a conventional manner to produce N-carbobenzoxy-D-phenylglycine.
    A 0.60 g portion of N-carbobenzoxy-D-phenylglycine is dissolved in 10 ml of dry tetrahydrofuran. The solution is cooled in an ice-salt bath, and to it is added 0.29 ml of triethylamine with stirring over a period of 10 minutes, followed by 0.29 ml of isobutyl chloroformate, after which stirring is continued for 10 minutes at -5°C. During this time, 0.57 g of 7-aminocephalosporanic acid and 0.29 ml of triethylamine are dissolved in 5 ml of tetrahydrofuran and 5 ml of water, and the solution is centrifuged to remove a dark sludge. The clarified solution is cooled in ice and slowly added to the reaction mixture, and stirring is continued in the ice bath for 0.5 hour, followed by one hour at room temperature.
    The reaction product mixture is a homogenous solution having a pH of about 6. It is evaporated under vacuum to a semisolid residue. To the residue are added 35 ml of water and a few drops of triethylamine to raise the pH to 8. The aqueous solution obtained thereby is extracted successively with 50 ml and 35 ml portions of ethyl acetate, the pH being adjusted to 2 at each extraction with hydrochloric acid. The extracts are combined, filtered, dried over sodium sulfate, stripped of solvent, and evaporated under vacuum. The product is 7-(N-carbobenzoxy-D-α-aminophenylacetamido)cephalosporanic acid in the form of a yellow-white amorphous solid weighing 1.10 g.
    Of this material 1.0 g is dissolved in 150 ml of warm 95% ethyl alcohol. To the solution is added 1.0 g of 5% palladium on carbon catalyst, and the mixture is hydrogenated at room temperature and atmospheric pressure by bubbling hydrogen into it for 3 hours with stirring. The hydrogenation product is filtered. The solid phase, comprising the catalyst and the desired product, is suspended in ethyl acetate and water and adjusted to pH 2 with hydrochloric acid. The suspension is filtered to remove the catalyst. The aqueous phase is separated from the filtrate, and is evaporated under vacuum to recover the desired product, 7-(D-α-aminophenylacetamido)cephalosporanicacid.
  • brand nameKafocin (Lilly).
  • Therapeutic FunctionAntibacterial
cefaloglycin Preparation Products And Raw materials
cefaloglycin (3577-01-3)Related Product Information
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