Cefazolin

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

"Ancef" redirects here. For the similarly spelled trade name, see Encef.
Cefazolin
Clinical data
Pronunciation/səˈfæzələn/
Trade namesAncef, Cefacidal, other
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B1
Routes of
administration		intravenous, intramuscular
Drug classFirst-generation cephalosporin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNA
Metabolism?
Elimination half-life1.8 hours (given IV)
2 hours (given IM)
Excretionkidney, unchanged
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.042
Chemical and physical data
FormulaC14H14N8O4S3
Molar mass454.50 g·mol−1
3D model (JSmol)
Melting point198 to 200 °C (388 to 392 °F) (decompose.)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O
  • InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1 Y
  • Key:MLYYVTUWGNIJIB-BXKDBHETSA-N Y
  (verify)

Common side effects include diarrhea, vomiting, yeast infections, and allergic reactions. Historically, it was thought to be contraindicated in patients with allergies to penicillin, although several recent studies have refuted this and it is proven to be safe in almost all patients, including those with known penicillin allergies. It is relatively safe for use during pregnancy and breastfeeding. Cefazolin is in the first-generation cephalosporin class of medication and works by interfering with the bacteria's cell wall.

Cefazolin was patented in 1967 and came into commercial use in 1971. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

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