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| | Cefazolin sodium salt Chemical Properties |
| Melting point | 190 °C | | refractive index | 20 ° (C=10, H2O) | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | H2O: 50 mg/mL, clear, colorless | | form | crystalline powder | | color | White to Off-White | | Sensitive | Light Sensitive | | Merck | 14,1917 | | BRN | 3585038 | | Stability: | Stable, but may be heat sensitive - store in cool conditions. May discolour upon exposure to light - store in the dark. Incompatible with strong oxidizing agents. | | InChIKey | LJIOGPYKTPCRAP-MVOALHSDNA-N | | SMILES | C(C1=C(CS[C@]2([H])[C@H](NC(=O)CN3N=NN=C3)C(=O)N12)CSC1=NN=C(C)S1)(=O)O.[NaH] |&1:5,7,r| | | LogP | 1.133 (est) | | CAS DataBase Reference | 27164-46-1(CAS DataBase Reference) |
| | Cefazolin sodium salt Usage And Synthesis |
| Brand Name(s) in US | Ancef, Kefzol, and generic
| | Chemical Properties | White to off-white powder | | Originator | Cefamedin,Fujisawa,Japan,1971 | | Uses | Semi-synthetic antibiotic derived from 7-amino-cepphalosporanic acid. An antibacterial | | Uses | enzyme inhibitor, Gaucher's disease therapy | | Uses | Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial. | | 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. | | 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. | | Brand name | Ancef (GlaxoSmithKline);
Kefzol (Lilly). | | Therapeutic Function | Antibacterial | | Biological Activity | cefazolin is a semisynthetic antibiotic with a broad spectrum of antibacterial activity. cefazolin has exhibited high activity against gram-positive bacteria and gram-negative bacteria [1]. | | 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. | | 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. | | in vitro | in cultured mg-63 human osteosarcoma cell line, cefazolin (100 μg/ml) showed little or no effect on osteoblast replication. cefazolin (200μg/ml) significantly decreased cell replication, and 10,000 μg/ml caused cell death [2]. | | in vivo | in patients with normal and various degrees of compromised renal function, administration of cefazolin significantly decreased the urinary concentration and percentage of the dose excreted in the urine [3]. the half-life of cefazolin in serum of normal persons was 1.9 hr and as long as 35 hr in severely uremic patients. in uremic patients, cefazolin was well tolerated [4]. | | references | [1] kariyone k, harada h, kurita m, et al. cefazolin, a new semisynthetic cephalosporin antibiotic. i[j]. the journal of antibiotics, 1970, 23(3): 131-136.
[2] edin m l, miclau t, lester g e, et al. effect of cefazolin and vancomycin on osteoblasts in vitro[j]. clinical orthopaedics and related research, 1996, 333: 245-251.
[3] levison m e, levison s p, ries k, et al. pharmacology of cefazolin in patients with normal and abnormal renal function[j]. journal of infectious diseases, 1973, 128(supplement 2): s354-s357.
[4] craig w a, welling p g, jackson t c, et al. pharmacology of cefazolin and other cephalosporins in patients with renal insufficiency[j]. journal of infectious diseases, 1973, 128(supplement 2): s347-s353. |
| | Cefazolin sodium salt Preparation Products And Raw materials |
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