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Cefazolin information


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
  • J01DB04 (WHO) QJ51DB04 (WHO)
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
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 checkY
PubChem CID
  • 33255
DrugBank
  • DB01327 checkY
ChemSpider
  • 30723 checkY
UNII
  • IHS69L0Y4T
KEGG
  • D02299 checkY
ChEBI
  • CHEBI:474053 checkY
ChEMBL
  • ChEMBL1435 checkY
CompTox Dashboard (EPA)
  • DTXSID2022753 Edit this at Wikidata
ECHA InfoCard100.043.042 Edit this at Wikidata
Chemical and physical data
FormulaC14H14N8O4S3
Molar mass454.50 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point198 to 200 °C (388 to 392 °F) (decompose.)
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 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. 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.

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intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agents cefalexin and cefadroxil. Cefalotin sodium is marketed...

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disrupt the synthesis of the peptidoglycan layer of bacterial cell walls. Cefazolin Ancef, Kefzol Cephradine Cephapirin Cephalothin Cefalexin Keflex Cephalosporins...

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Charlton M, Serur D (2006). "Serum sickness-like reaction associated with cefazolin". BMC Clin Pharmacol. 6: 3. doi:10.1186/1472-6904-6-3. PMC 1397863. PMID 16504095...

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Benzathine benzylpenicillin

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sodium. The cephalosporin series includes intermediate 7-ACA, cefazolin sodium, cefazolin acid and ceftriaxone sodium. Meropenem API is also produced....

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Group B streptococcal infection

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