Cefatrizine

Cefatrizine Basic information
Product Name:Cefatrizine
Synonyms:CEFATRIZINE;CEFATRIZINE PROPYLENE GLYCOL;7-[2-(4-hydroxyphenyl)-2-aminoacetamido]-3-(1,2,3-triazole-4-ylthio)methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;antibioticbl-640;antibioticbl-s640;bls640;cephatriazine;eta(r)))-
CAS:51627-14-6
MF:C18H18N6O5S2
MW:462.5
EINECS:257-324-2
Product Categories:
Mol File:51627-14-6.mol
Cefatrizine Structure
Cefatrizine Chemical Properties
Boiling point 948.1±65.0 °C(Predicted)
density 1.3806 (rough estimate)
refractive index 1.7000 (estimate)
storage temp. Store at -20°C
solubility DMSO: 95 mg/mL (201.02 mM);Ethanol: 23 mg/mL (48.67 mM)
pka2?+-.0.50(Predicted)
Water Solubility Water: 95 mg/mL (201.02 mM)
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)
MSDS Information
Cefatrizine Usage And Synthesis
OriginatorBricef,Bristol Banyu,Japan,1980
UsesCefatrizine is a new orally administered cephalosporin with excellent activity against gram-positive cocci, inhibiting all except enterococci at minimal inhibitory concentrations below 1 μg/ml.
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.
Cefatrizine Preparation Products And Raw materials
Raw materialsFormic acid
7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid CEFADROXIL Cephalexin Zileuton Cefatrizine P.G Jp13 7-TACA / for Cefatrizine 5-Methylmercapto-1,2,3-triazole Cefatrizine CEFATRIZINE PROPYLENE GLYCOL EPC(CRM STANDARD),CEFATRIZINE PROPYLENE GLYCOL EPC(CRM STANDARD) CEFATRIZINE PROPYLENE GLYCOL,CEFATRIZINE PROPYLENE GLYCOL,propyleneglycol-cefatrizin 7-TACA for cefatrizine P.G Cefatrizine propylene glycolate 7-amino-3-(1,2,3-triazole-4-ylthio)methyl cephalosporanic acid Inter.cefatrizine (7-TACA) CEFATRIZINE IMPURITY A

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