Cefazolin

"Ancef" redirects here. For the similarly spelled trade name, see Encef.
Cefazolin
Clinical data
Pronunciation/səˈfæzələn/[1]
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 Edit this at Wikidata
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 checkY
  • Key:MLYYVTUWGNIJIB-BXKDBHETSA-N checkY
  (verify)

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections.[2] Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections.[2] It is also used to prevent group B streptococcal disease around the time of delivery and before surgery.[2] It is typically given by injection into a muscle or vein.[2]

Common side effects include diarrhea, vomiting, yeast infections, and allergic reactions.[2] 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.[3] It is relatively safe for use during pregnancy and breastfeeding.[2][4] Cefazolin is in the first-generation cephalosporin class of medication and works by interfering with the bacteria's cell wall.[2]

Cefazolin was patented in 1967 and came into commercial use in 1971.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication.[2]

  1. ^ "Cefazolin". Merriam-Webster.com Dictionary. Merriam-Webster. Retrieved 2016-01-21.
  2. ^ a b c d e f g h "Cefazolin Sodium". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
  3. ^ "NEJM Journal Watch: Summaries of and commentary on original medical and scientific articles from key medical journals". www.jwatch.org. Retrieved 2023-01-20.
  4. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 84. ISBN 9781284057560.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN 9783527607495. Archived from the original on 2017-09-10.
  6. ^ US patent 3516997, Takano T, Kurita M, Nikaido H, Mera M, Konishi N, Nakagawa R, "3,7-disubstituted cephalosporin compounds and preparation thereo", published 1970-06-23, issued 1970-06-23, assigned to Fujisawa Pharmaceutical Co Ltd 
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.