| Identification | More | [Name]
Cefatrizine | [CAS]
51627-14-6 | [Synonyms]
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
CEFATRIZINE
CEFATRIZINE PROPYLENE GLYCOL
antibioticbl-640
antibioticbl-s640
bls640
cephatriazine
eta(r)))-
l)acetyl)amino)-8-oxo-3-((1h-1,2,3-triazol-4-ylthio)methyl)-,(6r-(6-alpha,7-b
s640p
Cephathiamidine
CEFATRIZINE IMPURITY A7-AMINO-(6R,7R)-3-[(2H-1,2,3-TRIAZOL-4-YL)SULFANYL]-METHYL-8-OXO-5-THIA-1-AZABICYCLO[4.2.O]OCT-2-ENE-2-CARBOXYLIC ACID(7-ACA TRIAZOLE) EPC(CRM STANDARD)
CEPHATHIAMIDINUM
(6R,7R)-7-[[2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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
SKF-60771 | [EINECS(EC#)]
257-324-2 | [Molecular Formula]
C21H26N6O7S2 | [MDL Number]
MFCD00274172 | [Molecular Weight]
538.6 | [MOL File]
51627-14-6.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [Originator]
Bricef,Bristol Banyu,Japan,1980 | [Uses]
Antidepressant, Selective serotonin reuptake inhibitor | [Uses]
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. | [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. | [storage]
Store at -20°C |
| Safety Data | Back Directory | [Toxicity]
LD50 in male, female mice, male, female rats (mg/kg): 6880, 6410, 4325, 4325 i.p. (Matsuzaki) |
|
|