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Cefatrizine

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Cefatrizine Basic information
Cefatrizine Chemical Properties
  • Boiling point:948.1±65.0 °C(Predicted)
  • Density 1.3806 (rough estimate)
  • refractive index 1.7000 (estimate)
  • pka2?+-.0.50(Predicted)
  • CAS DataBase Reference51627-14-6(CAS DataBase Reference)
Safety Information
  • ToxicityLD50 in male, female mice, male, female rats (mg/kg): 6880, 6410, 4325, 4325 i.p. (Matsuzaki)
Cefatrizine Usage And Synthesis
  • OriginatorBricef,Bristol Banyu,Japan,1980
  • UsesAntidepressant, Selective serotonin reuptake inhibitor
  • DefinitionChEBI: A cephalosporin compound having (1H-1,2,3-triazol-4-ylsulfanyl)methyl and [(2R)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. An antibacterial drug first prepared in the 1970s, it has more recently been found to be n inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of human cancers.
  • Manufacturing ProcessA total 6.5 g (1 1.55 mmol) of 7-[D-α-t-butoxycarbonylamino-α-(p-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4- carboxylic acid was dissolved in 175 ml (98 to 100% formic acid under anhydrous conditions. The mixture was stirred at room temperature for 2.5 hours. Part of the solution, 125 ml, was evaporated under reduced pressure to an amber oil. The oil was then azeotroped 3 times with 70 ml of toluene under reduced pressure. The residue was suspended in an 80:20 H2O-CH3OH solution (700 ml) and stirred for 0.5 hour until most of the solid dissolved, then filtered. The filtration was treated with 1.59 of (Darko) charcoal for about 20 minutes. The charcoal was filtered off through a Celite pad. The solution was then freeze-dried in 9 separate 100 ml round bottom flasks. The freeze-dried material weighed 2.415 g. It was recrystallized in batches of 0.200 g as described above to yield a total of 0.923 g 7-[D-α-amino-α-(p-hydroxyphenyl) acetamidol-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid. NMR was consistent, indicating the presence of 0.33 mol of CH3OH.
  • Therapeutic FunctionAntibiotic
  • Antimicrobial activityA semisynthetic cephalosporin formulated for oral use. The spectrum is similar to that of cefalexin but it is more active against H. influenzae. Wide strain variations in susceptibility have been reported.
    It is only partially absorbed when given by mouth. A 500 mg oral dose achieves a concentration of c. 6 mg/L after 1–2 h. The normal half-life of 2.5 h is extended to 5.5 h in end-stage renal failure. Distribution resembles that of cefalexin. It crosses the placenta readily. Plasma protein binding is 40–60%.
    Urinary recovery in 6 h is 35% of an oral dose, producing urinary levels of 50–1500 mg/L. It is presumed that the remainder is metabolized, but no metabolites have been identified.
    Apart from some mild diarrhea, it is well tolerated. It is available in Japan.
  • Safety ProfileModerately toxic byintraperitoneal and subcutaneous routes. An experimentalteratogen. Other experimental reproductive effects. Whenheated to decomposition it emits very highly toxic fumesof NOx and SOx.
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