 Home > Encyclopedia > Ceftiolene

Ceftiolene

Ceftiolene structure

CAS No:
77360-52-2
Formula:
C20H18N8O8S3
Chemical Name:
Ceftiolene
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1E)-2-[[1,4,5,6-tetrahydro-5,6-dioxo-4-(2-oxoethyl)-1,2,4-triazin-3-yl]thio]ethenyl]-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[2-[[1,4,5,6-tetrahydro-5,6-dioxo-4-(2-oxoethyl)-1,2,4-triazin-3-yl]thio]ethenyl]-,[6R-[3(E),6α,7β(Z)]]-;(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1E)-2-[[1,4,5,6-tetrahydro-5,6-dioxo-4-(2-oxoethyl)-1,2,4-triazin-3-yl]thio]ethenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Ceftiolene;RP 42980;Cefatiolene;Cefathiolene
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Ceftiolene is a cephalosporin compound having (E)-2-{[5,6-dioxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]sulfanyl}ethenyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups; a third-generation cephalosporin antibiotic. It has a role as an antibacterial drug.|Ceftiolene is a semisynthetic, broad-spectrum, third-generation cephalosporin with antibacterial activity. Ceftiolene 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.

Ceftiolene Basic Attributes

Molecular Weight：

594.608

Exact Mass：

594.60

UNII：

28TV2P33KF

NCI Thesaurus Code：

C76175

Characteristics

PSA：

305

XLogP3：

-1.3

Drug Information

MeSH Entry Terms：

cefatiolene

Ceftiolene Use and Manufacturing

A third-generation cephalosporin; β-lactam antibiotic.

Computed Properties

Molecular Weight:594.6
XLogP3:-1.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:10
Exact Mass:594.04097308
Monoisotopic Mass:594.04097308
Topological Polar Surface Area:305
Heavy Atom Count:39
Complexity:1240
Defined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes