Cefbuperazone

Cefbuperazone is a second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and {N-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-D-threonyl}amino side groups located at positions 3 and 7beta respectively. It is a peptide and a cephalosporin.|Cefbuperazone is a semisynthetic second-generation cephalosporin with antibacterial activity. Cefbuperazone 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.

Reaction of 4-ethyl-2, 3-dioxo-1-piperazinecarboxylic acid chloride (I) with D-threonine to obtain compound (II). Then react with compound (III) to obtain compound (IV). After introducing the 7-position methoxy group with lithium methoxide, the benzhydryl group is removed by hydrolysis with trifluoroacetic acid to obtain cefrazone.

Used for septicemia, chronic bronchitis, pneumonia, pulmonary purulent disease, endocarditis, cholecystitis caused by sensitive bacteria such as Escherichia coli, Serratia, common and exotic Proteus, Haemophilus influenzae, pneumococcus , Peritonitis, cystitis, etc.

Molecular Weight:627.7
XLogP3:-1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:10
Exact Mass:627.15296588
Monoisotopic Mass:627.15296588
Topological Polar Surface Area:280
Heavy Atom Count:42
Complexity:1210
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes