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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H18N8O8S3
Molecular Weight 594.601
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFTIOLENE

SMILES

[H][C@]12SCC(\C=C\SC3=NNC(=O)C(=O)N3CC=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O

InChI

InChIKey=WJXAHFZIHLTPFR-JLRJEBFFSA-N
InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H18N8O8S3
Molecular Weight 594.601
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Ceftiolene (42980RP) is a new cephalosporin with a broad antibacterial spectrum similar to cefotaxime or ceftriaxone. The affinities of ceftiolene for penicillin-binding proteins are very comparable with those of ceftriaxone and cefotaxime for Escherichia coli, and generally greater than those of latamoxef (moxalactam) for the higher molecular weight PBPs of E. coli. Enterobacter cloacae. The affinity of ceftiolene for PBP1 of Staphylococcus aureus is greater than those of cefotaxime or latamoxef but comparable with these antibiotics for PBP3. The bacteriolytic activity of ceftiolene at defined concentrations against Gram-negative organisms is similar to that of ceftriaxone and significantly better than that of the other third-generation cephalosporins tested.

Originator

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
28TV2P33KF
Record Status Validated (UNII)
Record Version