Cefazolin

Cefazolin
Clinical data


Pronunciation	/sɪˈfæzələn/
Trade names	Ancef, Cefacidal, other
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Routes of administration	intravenous, intramuscular
ATC code	J01DB04 (WHO) QJ51DB04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	NA
Metabolism	?
Biological half-life	1.8 hours (given IV) 2 hours (given IM)
Excretion	kidney, unchanged
Identifiers
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
CAS Number	25953-19-9^Y
PubChem CID	33255
DrugBank	DB01327^Y
ChemSpider	30723^Y
UNII	IHS69L0Y4T
KEGG	D02299^Y
ChEBI	CHEBI:474053^Y
ChEMBL	CHEMBL1435^Y
ECHA InfoCard	100.043.042
Chemical and physical data
Formula	C₁₄H₁₄N₈O₄S₃
Molar mass	454.51 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nnc(s4)C)C(=O)O
InChI 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

Cefazolin, also known as cefazoline and cephazolin, is an 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 around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

Common side effects include diarrhea, vomiting, yeast infections, and allergic reactions. It is not recommended in people who have a history of anaphylaxis to penicillin. 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, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is about 1.20 to 1.41 USD per day. In the United States a course of treatment costs 25 to 50 USD.