CEFSUMIDE

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 Search

SMILES

CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CC=CC(NS(C)(=O)=O)=C3)C2=O)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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16270182 | https://www.ncbi.nlm.nih.gov/pubmed/15781398 | https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19741128&CC=DE&NR=2422385A1&KC=A1

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

Title	Date	PubMed
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.	2006-02	16270182

Patents

Name

Type

Language

CEFSUMIDE

Official Name

English

CEFSULMID [JAN]

Preferred Name

English

cefsumide [INN]

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