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Brand Name(s) in US
Ancef, Kefzol, and generic
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Chemical Properties
White to off-white powder
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Originator
Cefamedin,Fujisawa,Japan,1971
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Uses
Semi-synthetic antibiotic derived from 7-amino-cepphalosporanic acid. An antibacterial
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Uses
Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial.
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Uses
enzyme inhibitor, Gaucher's disease therapy
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Definition
ChEBI: A cephalosporin organic sodium salt having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups.
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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.
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brand name
Ancef (GlaxoSmithKline);
Kefzol (Lilly).
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Therapeutic Function
Antibacterial
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Clinical Use
Cefazolin (Ancef, Kefzol) is one of a series of semisyntheticcephalosporins in which the C-3 acetoxy function has beenreplaced by a thiol-containing heterocycle—here, 5-methyl-2-thio-1,3,4-thiadiazole. It also contains the somewhatunusual tetrazolylacetyl acylating group. Cefazolin wasreleased in 1973 as a water-soluble sodium salt. It is activeonly by parenteral administration.
Cefazolin provides higher serum levels, slower renalclearance, and a longer half-life than other first-generationcephalosporins. It is approximately 75% protein bound inplasma, a higher value than for most other cephalosporins.Early in vitro and clinical studies suggest that cefazolin ismore active against Gram-negative bacilli but less activeagainst Gram-positive cocci than either cephalothin orcephaloridine. Occurrence rates of thrombophlebitis followingintravenous injection and pain at the site of intramuscularinjection appear to be the lowest of the parenteralcephalosporins.
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Veterinary Drugs and Treatments
In the United States, there are no cefazolin products approved for
veterinary species but it has been used clinically in several species
when an injectable, first generation
cephalosporin is indicated. It is
used for surgical prophylaxis, and for variety of systemic infections
(including orthopedic, soft tissue, sepsis) caused by susceptible bacteria.
Most commonly given every 6 – 8 hours via parenteral routes,
cefazolin constant rate intravenous infusion protocols are being
developed as cefazolin is a time (above MIC)-dependent antibiotic,
and serum/tissue concentrations can remain above MIC.
