25953-19-9 Usage
Description
Cefazolin is a cephalosporin antibiotic derived from 7-amino-cephalosporanic acid, characterized by a thio-linked thiadiazole ring at the C-3 position and a tetrazoylmethylene unit at C-7. It is known for its lower irritation upon injection, longer half-life compared to cephapirin, and comparative instability, requiring protection from heat and light.
Uses
Used in Pharmaceutical Industry:
Cefazolin is used as an antibacterial agent for systemic infections. It is effective in treating a wide range of bacterial infections due to its ability to disrupt bacterial cell wall synthesis, leading to cell lysis and death. Its longer half-life and lower irritation upon injection make it a preferred choice in the treatment of various infections.
Additionally, Cefazolin's chemical properties, such as its needle-like structure, may have potential applications in other industries, although the provided materials do not specify any such uses.
Originator
Cefamedin,Fujisawa,Japan,1971
Manufacturing Process
7-Aminocephalosporanic acid is converted to its sodium salt and acylated with
1H-tetrazole-1-acetyl chloride. The acetoxy group is then displaced by
reaction with 5-methyl-1,3,4-thiadiazole-2-thiol in buffer solution. The product
acid is converted to the sodium salt by NaHCO3.
Therapeutic Function
Antibacterial
Antimicrobial activity
Enterobacter, Klebsiella, Providencia, Serratia spp.
and Pr. vulgaris are all resistant. B. fragilis is resistant, but
other anaerobes are susceptible.
Pharmacokinetics
Distribution
The volume of distribution is the smallest of the cephalosporins
in group 1, perhaps an indication of relative confinement
to the plasma space. It crosses inflamed synovial
membranes, but the levels achieved are well below those
of the simultaneous serum levels and entry to the CSF is
poor. In patients receiving 10 mg/kg by intravenous bolus,
mean concentrations in cancellous bone were 3.0 mg/kg
when the mean serum concentration was 33 mg/L, giving
a bone:serum ratio of 0.09. Some crosses the placenta,
but the concentrations found in the fetus and membranes
are low.
Metabolism and excretion
It is not metabolized. Around 60% of the dose is excreted
in the urine within the first 6 h, producing concentrations
in excess of 1 g/L. Excretion is depressed by probenecid.
The renal clearance is around 65 mL/min and declines in
renal failure, when the half-life may rise to 40 h, although levels
in the urine sufficient to inhibit most urinary pathogens
are still found. It is moderately well removed by hemodialysis
and less well by peritoneal dialysis.
Levels sufficient to inhibit a number of enteric organisms
likely to infect the biliary tract are found in T-tube bile (17–31
mg/L after a 1 g intravenous dose), but this is principally due
to the high serum levels of the drug and the total amounts
excreted via the bile are small.
Clinical Use
Cefazolin has been widely used in surgical prophylaxis,
especially in biliary tract (because of the moderately high
concentrations achieved in bile), orthopedic, cardiac and
gynecological surgery.
Side effects
Side effects are those common to other cephalosporins
,including rare bleeding disorders and encephalopathy
in patients in whom impaired excretion or direct instillation
leads to very high CSF levels. Neutropenia has been
described and hypoprothrombinemic bleeding has been
attributed to the side chain.
Synthesis
Cefazolin, (6R-trans)-3[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-
7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabycyclo[4.2.0]oct-2-en-2-carboxylic acid
(32.1.2.7), is synthesized by reacting 7-aminocephalosporanic acid with a mixed anhydride (32.1.2.6), which is the result of a reaction of tetrazolylacetic acid with pivalic
(trimethylacetic) acid chloride. Further reaction with 2-mercapto-5-methyl-1,3,4-thiadiazole results in a substitution of the 3-acetoxy group with a mercaptothiadiazol group, giving cefazolin (32.1.2.7).
Check Digit Verification of cas no
The CAS Registry Mumber 25953-19-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,9,5 and 3 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 25953-19:
(7*2)+(6*5)+(5*9)+(4*5)+(3*3)+(2*1)+(1*9)=129
129 % 10 = 9
So 25953-19-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
25953-19-9Relevant articles and documents
Chemoenzymatic one-pot synthesis of cefazolin from cephalosporin C in fully aqueous medium, involving three consecutive biotransformations catalyzed by D-aminoacid oxidase, glutaryl acylase and penicillin G acylase
Fernandez-Lafuente, Roberto,Guisan, Jose M.,Pregnolato, Massimo,Terreni, Marco
, p. 4693 - 4696 (1997)
A new chemoenzymatic synthesis of Cefazolin through the correct assembly of three biotransformations catalyscd by D-aminoacid oxidase, glutaryl acylase and penicillin G acylase is described. This multienzymatic synthesis has been performed from the natural Cephalosporin C in fully aqueous medium without intermediate purification stages. Almost quantitative yields have been achieved in all the enzymatic reactions.
Cefazolin sodium or composition thereof, preparation method thereof, preparations thereof and novel indication for genital system infection
-
, (2019/11/13)
The present invention provides cefazolin sodium or a composition thereof, a preparation method thereof, preparations thereof and use. The preparation method has high repeatability and a stable and reliable production process. The prepared cefazolin sodium or the composition thereof has a low impurity content, facilitating improvement in raw material quality and quality of corresponding preparations, and improvement in safety and clinical curative effects of preparations. The cefazolin sodium or the composition thereof can be used for preparing medicines treating genital system infection.
ORAL NEUROTHERAPEUTIC CEFAZOLIN COMPOSITIONS
-
Page/Page column 19, (2008/06/13)
The treatment of neurological disorders using cefazolin compositions and pharmaceutical compositions including oral dosage forms that include cefazolin compositions are described.