• Cefazolin sodium, USP packaged and labeled.

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SKU: C006

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Description

Cefazolin sodium, USP is a first generation cephalosporin.  It is a semi-synthetic, broad-spectrum β -lactam with bactericidal activity.  Cefazolin sodium is sparingly soluble in aqueous solution. (0.47 mg/mL).

    CAS Number

    27164-46-1

    Molecular Formula

    C14H13N8NaO4S3

    Molecular Weight

    476.49

    Mechanism of Action

    Like β-lactams, cephalosporins interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to cephalosporins is commonly due to cells containing plasmid encoded β-lactamases.

    Storage Conditions

    -20°C

    Tariff Code

    2941.90.5000

    Spectrum

    Cefazolin sodium is effective against Gram-positive and Gram-negative bacteria, especially those species causing skin infections.

Applications

    Eukaryotic Cell Culture Applications

    The reducing power of the cell involves Glucose-6-phosphate dehydrogenase (G6PD). The reprograming of nicotinamide adenine dinucleotide (NAD homeostasis is reported to be an important step in cancer progression. Rat erythrocyte G6PD enzyme was studied in vitro with cefazolin and it was found that the enzyme increased upon exposure to cefazolin (Temel et al, 2018).

    The toxicity of cephalosporin to rabbit kidney cells in vitro was compared to their known nephrotoxic potential in vivo. Researchers found that when they added a microsomal S9 fraction from rabit kidney was added to the culture, cephalothin was desacetylated and its toxicity to kidney cells was reduced. Desacetyl‐cephalothin was relatively nontoxic to rabbit renal tissue in vitro (Hottendorf et al, 1987).

    Microbiology Applications

    Cefazolin sodium is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:

    • Staphylococcus aureus 0.25 µg/mL -32 µg/mL
    • Staphylococcus epidermidis ≤0.06 µg/mL - >128 µg/mL
    • For a complete list of cefazolin MIC values, click here.

    Media Supplement

    Colistin is routinely used as a selection agent in several types of isolation media:

    Columbia Blood AgarCampylobacter selective supplement (Butzler)

Specifications

    Form

    Powder

    Appearance

    White or almost white powder

    Source

    Semi-synthetic

    Impurity Profile

    Impurity A| (6R,7R)-7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|30246-33-4|C11H12N4O3S3|344.44| Impurity B| (6R,7R)-7-[(2,2-dimethylpropanoyl)amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid||C16H20N4O4S3|428.55| Impurity C| (6R,7R)-3-methyl-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|56842-77-4|C11H12N6O4S|324.32| Impurity D| (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|32510-61-5|C13H14N6O6S|382.36| Impurity E| MMTD|29490-19-5|C3H4N2S2|132.2| Impurity G| (5aR,6R)-6-[(1H-tetazol-1-ylacetyl)amino-5a,6-dihydro 3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)-dione||C11H10N6O4S|322.30| Impurity H| 7-ACA|957-68-6|C10H12N2O5S|272.28| Impurity I| cefazoloic acid; 2-[carboxy[(1H-tetrazol-1-ylacetyl)amino]methyl]-5-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid||C14H16N8O5S3|472.53| Impurity J| hydrolysed cefazoloic acid; 2-[carboxy[(1H-tetrazol-1-ylacetyl)amino]methyl]-5-(hydroxymethyl)-5,6-dihydro-2H-1,3-thiazine-4-carboxylic acid||C11H14N6O6S|358.33| Impurity K| Cefazolinamide; (6R,7R)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxamide||C14H15N9O3S3|453.53| Impurity L| (6R,7S)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)sulphanyl]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1H-Tetrazole-1-acetic acid|21732-17-2|C3H4N4O2|128.09|

    Water Content (Karl Fischer)

    ≤6.0%

    pH

    4.0-6.0

    Optical Rotation

    -10° to -24°

    Assay

    (On Dried Basis): 89.1-110.1%

References

    References

    Georgopapadakou, NH (1992) Mechanisms of Action of Cephalosporin 3'-quinolone Esters, Carbamates, and Tertiary Amines in Escherichia Coli. 37(3): 559-565. Antimicrob. Agents and Chemother.

    Hottendorf GH, Laska DA, Williams PD & Ford SM (1987) Role of desacetylation in the detoxification of cephalothin in renal cells in culture, Journal of Toxicology and Environmental Health, 22(1): 101-111 PMID 3612832

    Pedroso TM and Salgado HRN (2014) Development and validation of a microbiological assay by turbidimetry to determine the potency of cefazolin sodium in the lyophilized powder form. Anal. Methods 6:1391-1396

    Reller LB, Karney WW, Beaty HN, Holmes KK, Turck M (1973) Evaluation of cefazolin, a new cephalosporin antibiotic. Antimicrob Agents Chemother. 3(4):488-97. PMID 4790605

    Ries K, Matthew E. Levison ME and Kaye D (1973) Clinical and In Vitro Evaluation of Cefazolin, a New Cephalosporin Antibiotic. Antimicrob. Agents and Chemother. 3 (2) 168-174 PMID 4790605

    Temel Y, Ayna A, Shafeeq IH and Ciftci M (2018) In vitro effects of some antibiotics on glucose-6-phosphate dehydrogenase from rat (Rattus norvegicus) erythrocyte. Drug and Chem. Toxicol. Jun 27:1-5. PMID 29947262

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