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Cefotiam

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Cefotiam Basic information
Cefotiam Chemical Properties
  • Boiling point:843℃
  • Density 1.80±0.1 g/cm3(Predicted)
  • RTECS XI0366000
  • Flash point:>110°(230°F)
  • storage temp. Sealed in dry,2-8°C
  • pka2.57±0.50(Predicted)
  • Water Solubility Soluble
  • CAS DataBase Reference61622-34-2(CAS DataBase Reference)
Cefotiam Usage And Synthesis
  • OriginatorCefotiam,Qingdao Ftz United International Inc.
  • UsesAntibacterial
  • DefinitionChEBI: A cephalosporin with ({1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl}sulfanyl)methyl and (2-amino-1,3-thiazol-4-yl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. A third generation beta-lactam cephalospo in antibiotic, it is active against a broad spectrum of both Gram positive and Gram negative bacteria.
  • Manufacturing Process2 mmol of 7-acetamindocephalosporinic acid in phosphate buffer (pH 7), 2 mmol of 1-(2-dimethylaminoethyl-1H-tetrazol-5-thiol and 2.2 mmol of sodium hydrogen carbonate are mixed and resulting solution was stirred at 60°-65°C for 16 hours. After cooling the mixture was adjusted pH 3.6 and hydrochloride of NH2OH was added to give 7-amino-3-[2-(2-dimethylaminoethyl)-2H-tetrazol-5-ylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2- carboxylic acid.
    0.4 g (2 mmol) of 2-(2-aminothiazol-4-yl)acetic acid hydrochloride in 10 ml of dimethylformamide are dissolved, 0.25 g (2.2 mmol) of N-hydroxysuccinimide and 0.412 g (2 mmol) of dicyclohexylcarbodiimide and the solution is allowed to stand at room temperature for 3 hours. The reaction mixture is subjected to filtration under suction to remove the precipitate of N,N'-dicyclohexylurea. The filtrate is added at a stroke to a solution of 2 mmol of above prepared 7- amino-3-[2-(2-dimethylaminoethyl)-2H-tetrazol-5-ylsulfanylmethyl]-8-oxo-5- thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 0.404 g (4 mmol) of triethylamine in 20 ml of dichloromethane and the mixed solution is stirred for 24 hours at room temperature. The solvent is distilled off under reduced pressure and the residue is adjusted pH from to 6 to 7 by adding a 10% aqueous solution of sodium hydrogen carbonate. The resultant solution is chromatographed on column of polystyrene resin (Amberlite XAD-2) and developed with water. The fractions containing the desired product are pooled and freeze-dried to obtain the title product.
  • brand nameCeradon (Takeda).
  • Therapeutic FunctionAntibiotic
  • Antimicrobial activityA semisynthetic cephalosporin formulated as the dihydrochloride for injection and as a prodrug ester, cefotiam hexetil, for oral administration. Activity is similar to that of cefuroxime, but it is somewhat more active against a range of enterobacteria .
    A 30-min intravenous infusion of the dihydrochloride produces a peak serum concentration of 35 mg/L; the corresponding concentration after a 1 g intramuscular dose is 17 mg/L. Oral absorption of the hexetil ester is around 65%. Food delays absorption of the ester. The plasma half-life is 0.6–1.1 h. Around 40% is bound to plasma protein. Urinary excretion is almost complete 4 h after the end of intravenous infusion, but only 50–67% is recovered unchanged; there is substantial non-renal elimination and some evidence of saturation of renal tubular excretion at doses above 2 g. In anuria the plasma elimination half-life rises to 13 h and plasma and renal clearances parallel creatinine clearance. A small amount is excreted in bile. In patients with cholelithiasis given 0.5 or 1 g intravenously, mean concentrations in gallbladder bile and gallbladder wall 30 min after the dose were around 17 and 32 mg/L, respectively. In patients with normal liver function, hepatic bile concentrations can exceed 1 g/L.
    It is generally well tolerated and has been used successfully to treat lower respiratory infections, skin and soft-tissue infection. It is not widely used, but is available in Japan and some other countries.
Cefotiam Preparation Products And Raw materials
Cefotiam(61622-34-2)Related Product Information
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