Chemistry:Ceftezole

Ceftezole

Clinical data
ATC code	J01DB12 (WHO)
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	26973-24-0
PubChem CID	65755
ChemSpider	59178 Y
UNII	2Z86SYP11W
KEGG	D07656 Y
ChEMBL	ChEMBL1697829
Chemical and physical data
Formula	C13H12N8O4S3
Molar mass	440.47 g·mol−1
3D model (JSmol)	Interactive image
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
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Ceftezole (or ceftezol) is a semisynthetic first-generation cephalosporin antibiotic.

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.

Note

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