Ceftezole

Ceftezole (or ceftezol) is a semisynthetic first-generation cephalosporin antibiotic.[1]

Ceftezole
Clinical data
ATC code
Identifiers
IUPAC name
  • (6R,7R)-8-oxo-7-{[2-(tetrazol-1-yl)acetyl]amino}-
    3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-
    1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.113.941
Chemical and physical data
FormulaC13H12N8O4S3
Molar mass440.47 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cn3nnnc3)CSc4nncs4)C(=O)O
InChI
  • InChI=1S/C13H12N8O4S3/c22-7(1-20-4-14-18-19-20)16-8-10(23)21-9(12(24)25)6(2-26-11(8)21)3-27-13-17-15-5-28-13/h4-5,8,11H,1-3H2,(H,16,22)(H,24,25)/t8-,11-/m1/s1 Y
  • Key:DZMVCVMFETWNIU-LDYMZIIASA-N Y

Ceftezole binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Ceftezole is having (1,3,4-thiadiazol-2-ylsulfanyl)methyl and [2-(1H-tetrazol-1-yl)acetamido side groups located at positions 3 and 7 respectively. It is a cephalosporin and a member of thiadiazoles.

References
  1. Berger SA (2021). "Ceftezole". GIDEON Guide to Antimicrobial Agents. Los Angeles: Gideon Informatics, Incorporated. p. 301. ISBN 978-1-4988-2958-8.

Note
  •  This article incorporates public domain material from Ceftezole (compound). National Center for Biotechnology Information - the National Library of Medicine - PubChem®.


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