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Cephaloridine

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Cephaloridine Basic information
Cephaloridine Chemical Properties
  • Melting point:184°C
  • alpha D +47.7° (c = 1.25 in water)
  • Density 1.3230 (rough estimate)
  • refractive index 1.6390 (estimate)
  • storage temp. 2-8°C
  • pka3.2(at 25℃)
  • Water Solubility >20g/L(21 ºC)
Safety Information
Cephaloridine Usage And Synthesis
  • OriginatorCeporin,Glaxo,UK,1964
  • UsesAntibacterial agent.
  • DefinitionChEBI: A cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C.
  • Manufacturing Process7-Aminocephalosporanic acid (5.00 g) which passed through a 100-mesh sieve was suspended in boiling ethyl acetate (200 ml), and 2-thienylacetyl chloride (Cagniant, Bull. Soc. Chim. France, 1949, 847) (4.42 g, 1.5 equiv.) was added in ethyl acetate (20 ml). The mixture was boiled under reflux for 40 minutes, cooled, and filtered. Aniline (5.03 ml) was added, and after 1 hour the mixture was extracted with 3% sodium hydrogen carbonate solution (1 x 150 ml, 2 x 100 ml, 1 x 50 ml) and the alkaline extracts washed with ethyl acetate (3 x 100 ml). The aqueous solution was acidified to pH 1.2, and extracted with ethyl acetate (2 x 150 ml). The ethyl acetate extract was washed with water (4 x 40 ml), dried (MgSO4), and concentrated in vacuo to low volume. The crude 7-2'-thienylacetamidocephalosporanic acid (2.5 g) which separated was collected by filtration. Evaporation of the filtrate gave a further 2.68 g (71%) of the product, which was purified by crystallization from ethyl acetate, then aqueous acetone, MP 150°C to 157°C (decomp.).
    7-2'-Thienylacetamidocephalosporanic acid (7.0 g) was suspended in water (60 ml) and stirred with pyridine (7 ml) until the acid dissolved. The resulting solution (pH 5.9) was kept at 35°C for 3 days, then filtered and extracted with methylene chloride (4 x 60 ml). The methylene chloride extract was back-extracted with a little water and the total aqueous solutions were then percolated through a column of Dowex 1 x 8 resin, (100 to 200 mesh, 150 g) in the acetate form at pH 4.3. The column was washed with water until the optical rotation of the eluate fell to zero and the eluate (500 ml) was freeze-dried. The residual white solid was dissolved in the minimum volume of methanol and after a few minutes the pyridine derivative crystallized; this is the cephaloridine product.
  • brand nameKefloridin (Lilly); Loridine (Lilly);Cepalorin;Faredina;Latorex;Lauridin.
  • Therapeutic FunctionAntibacterial
  • World Health Organization (WHO)Cefaloridine, a semi-synthetic cephalosporin antibiotic, was introduced into medicine in 1964 for the treatment of bacterial infections. It is considered to be the most toxic of the cephalosporins, and for this reason is now seldom used. Nevertheless, it still remains available in certain countries and the World Health Organization is not aware of restrictive actions taken elsewhere.
  • HazardModerately to very toxic.
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