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HomeProduct name listCefatrizine

Cefatrizine

  • CAS NO.:51627-14-6
  • Empirical Formula: C18H18N6O5S2
  • Molecular Weight: 462.5
  • MDL number: MFCD01940014
  • EINECS: 257-324-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-21 10:59:17
Cefatrizine Structural

What is Cefatrizine?

Description

Cefatrizine was synthesized by BristolMyers Co. and Smith Klein & French Laboratories in 1974. It shows two to four times higher activity against gram-positive and four to eight times higher activity against gram-negative bacteria than cephalexin. Cefatrizine also shows excellent oral absorption, and its in vivo activity is 30 to 500 times higher than that of cephalexin.

Originator

Bricef,Bristol Banyu,Japan,1980

The Uses of Cefatrizine

Cefatrizine 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.

The Uses of Cefatrizine

Antidepressant, Selective serotonin reuptake inhibitor

Definition

ChEBI: 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 Process

A 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 Function

Antibiotic

Antimicrobial activity

A 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 Profile

Moderately toxic byintraperitoneal and subcutaneous routes. An experimentalteratogen. Other experimental reproductive effects. Whenheated to decomposition it emits very highly toxic fumesof NOx and SOx.

Properties of Cefatrizine

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)
pka 2?+-.0.50(Predicted)
Water Solubility  Water: 95 mg/mL (201.02 mM)
CAS DataBase Reference 51627-14-6(CAS DataBase Reference)

Safety information for Cefatrizine

Computed Descriptors for Cefatrizine

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