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Cefazolin
Systematic (IUPAC) name
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1 H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS number 25953-19-9
ATC code J01DB04 QJ51DA04
PubChem 33255
DrugBank DB01327
ChemSpider 30723
Chemical data
Formula C 14H14N8O4S3  
Mol. mass 454.51 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability NA
Metabolism  ?
Half life 1.8 hours (given IV)
2 hours (given IM)
Excretion Renal, unchanged
Therapeutic considerations
Pregnancy cat. B1(AU) B(US)
Legal status Prescription only
Routes Intravenous, intramuscular
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Cefazolin (INN), also known as cefazoline or cephazolin, is a first generation cephalosporin antibiotic.

The drug is usually administrated either by intramuscular injection (injection into a large muscle) or intravenous infusion (intravenous fluid into a vein).

Contents

Indications

Cefazolin is mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci of Gram positive bacteria. These organisms are common on normal human skin. Resistance to cefazolin is seen in several species of bacteria.

Adverse effects

Side effects from cefazolin are not common. Possible side effects include diarrhea, stomach pain or upset stomach, vomiting, and rash.

Like that of several other cephalosporins, the chemical structure of cefazolin contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[1]

Brands

Cefazolin is marketed under the following brand names: Ancef, Cefacidal, Cefamezin, Cefrina, Elzogram, Faxilen, Gramaxin, Kefazol, Kefol, Kefzol, Kefzolan, Kezolin, Novaporin, and Zolicef.

References

  1. ^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". in Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. pp. 847. ISBN 0-07-143763-0. http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847. Retrieved 2009-07-03.  

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