51627-14-6 Usage
Description
Cefatrizine, also known as Cefadroxil, is a cephalosporin antibiotic that was first prepared in the 1970s. It is characterized by its (1H-1,2,3-triazol-4-ylsulfanyl)methyl and [(2R)-2-amino-2-(4-hydroxyphenyl)]acetamido side-groups. Cefatrizine exhibits excellent activity against gram-positive cocci, inhibiting all except enterococci at minimal inhibitory concentrations below 1 μg/ml. In addition to its antibacterial properties, it has been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which plays a role in regulating apoptosis, autophagy, and ER stress in various types of human cancers.
Uses
Used in Pharmaceutical Industry:
Cefatrizine is used as an antibiotic for the treatment of bacterial infections, particularly those caused by gram-positive cocci. Its excellent activity against these bacteria makes it a valuable option for combating infections.
Used in Anticancer Applications:
Cefatrizine is used as an inhibitor of eEF2K, which is involved in the regulation of apoptosis, autophagy, and ER stress in many types of human cancers. By targeting this enzyme, Cefatrizine may help in the development of novel cancer therapies.
Used in Antidepressant Applications:
Cefatrizine is used as a selective serotonin reuptake inhibitor (SSRI), which helps in the treatment of depression and other mood disorders by increasing the availability of serotonin in the brain.
Originator
Bricef,Bristol Banyu,Japan,1980
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.
Check Digit Verification of cas no
The CAS Registry Mumber 51627-14-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,6,2 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 51627-14:
(7*5)+(6*1)+(5*6)+(4*2)+(3*7)+(2*1)+(1*4)=106
106 % 10 = 6
So 51627-14-6 is a valid CAS Registry Number.
InChI:InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)
