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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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Non-stochastic and stochastic linear indices of the molecular pseudograph's atom-adjacency matrix: a novel approach for computational in silico screening and "rational" selection of new lead antibacterial agents.
2006 Feb
Patents
Name Type Language
CEFSUMIDE
INN  
INN  
Official Name English
cefsumide [INN]
Common Name English
CEFSULMID [JAN]
Common Name English
(6R,7R)-7-((2R)-2-AMINO-2-(M-METHANESULFONAMIDOPHENYL)ACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
Code System Code Type Description
CAS
54818-11-0
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
EVMPD
SUB07421MIG
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
FDA UNII
3642W81J7A
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
PUBCHEM
68718
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
NCI_THESAURUS
C76037
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
WIKIPEDIA
Cefsumide
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID301023907
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL2375142
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
SMS_ID
100000081812
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
MESH
C012135
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY
INN
4297
Created by admin on Fri Dec 15 16:12:24 GMT 2023 , Edited by admin on Fri Dec 15 16:12:24 GMT 2023
PRIMARY