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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H20N4O6S2
Molecular Weight 440.494
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFSUMIDE

SMILES

[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC(NS(C)(=O)=O)=C3)C(O)=O

InChI

InChIKey=OFKRKCHCYWQZLY-XHBSWPGZSA-N
InChI=1S/C17H20N4O6S2/c1-8-7-28-16-12(15(23)21(16)13(8)17(24)25)19-14(22)11(18)9-4-3-5-10(6-9)20-29(2,26)27/h3-6,11-12,16,20H,7,18H2,1-2H3,(H,19,22)(H,24,25)/t11-,12-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H20N4O6S2
Molecular Weight 440.494
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cefsumide is an antibiotic of the cephalosporin group patented by Fujisawa Pharmaceutical Co. Cefsumide 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.

Originator

Approval Year

PubMed

Substance Class Chemical
Record UNII
3642W81J7A
Record Status Validated (UNII)
Record Version