Cefazolin

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Cefazolin
Systematic (IUPAC) name
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade namesAncef, Kefzol
AHFS/Drugs.commonograph
Pregnancy cat.B1 (AU) B (US)
Legal status Prescription only
RoutesIntravenous, intramuscular
Pharmacokinetic data
BioavailabilityNA
Metabolism ?
Half-life1.8 hours (given IV)
2 hours (given IM)
ExcretionRenal, unchanged
Identifiers
CAS number25953-19-9 YesY
ATC codeJ01DB04 QJ51DB04
PubChemCID 33255
DrugBankDB01327
ChemSpider30723 YesY
UNIIIHS69L0Y4T YesY
KEGGD02299 YesY
ChEBICHEBI:474053 YesY
ChEMBLCHEMBL1435 YesY
Chemical data
FormulaC14H14N8O4S3 
Mol. mass454.51 g/mol
 YesY (what is this?)  (verify)
 
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Cefazolin
Systematic (IUPAC) name
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade namesAncef, Kefzol
AHFS/Drugs.commonograph
Pregnancy cat.B1 (AU) B (US)
Legal status Prescription only
RoutesIntravenous, intramuscular
Pharmacokinetic data
BioavailabilityNA
Metabolism ?
Half-life1.8 hours (given IV)
2 hours (given IM)
ExcretionRenal, unchanged
Identifiers
CAS number25953-19-9 YesY
ATC codeJ01DB04 QJ51DB04
PubChemCID 33255
DrugBankDB01327
ChemSpider30723 YesY
UNIIIHS69L0Y4T YesY
KEGGD02299 YesY
ChEBICHEBI:474053 YesY
ChEMBLCHEMBL1435 YesY
Chemical data
FormulaC14H14N8O4S3 
Mol. mass454.51 g/mol
 YesY (what is this?)  (verify)

Cefazolin (INN), also known as cefazoline or cephazolin, is a first-generation cephalosporin antibiotic.

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

Indications[edit]

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. Cefazolin is extensively used as prophylaxis antibiotic before wide range of surgical operations.

Spectrum of bacterial susceptibility[edit]

Cefazolin is a broad spectrum antibiotic and can be used to treat different types of infections including urinary tract, skin, and bone infections. The following represents MIC susceptibility data for a few medically significant bacteria.

[1]

Adverse effects[edit]

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

Like those of several other cephalosporins, the chemical structure of cefazolin contains an N-methylthiodiazole (NMTD or 1-MTD) side-chain. As the antibiotic is broken down in the body, it releases free NMTD, 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.[2]

Brands[edit]

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

References[edit]

  1. ^ http://www.toku-e.com/Assets/MIC/Cefazolin%20sodium%20USP.pdf
  2. ^ 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. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03. 

External links[edit]