U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18N4O5S3
Molecular Weight 478.565
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFCANEL

SMILES

[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)[C@H](O)C4=CC=CC=C4)C(O)=O

InChI

InChIKey=VDFFPBOAOLQAJV-SUYBPPKGSA-N
InChI=1S/C19H18N4O5S3/c1-9-21-22-19(31-9)30-8-11-7-29-17-12(16(26)23(17)13(11)18(27)28)20-15(25)14(24)10-5-3-2-4-6-10/h2-6,12,14,17,24H,7-8H2,1H3,(H,20,25)(H,27,28)/t12-,14-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H18N4O5S3
Molecular Weight 478.565
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Cefcanel is a semisynthetic third-generation cephalosporin with antibacterial activity. Cefcanel is active against the species E. coli, K. aerogenes and Proteus mirabilis; H. influenzae and M. catarrhalis has reasonable susceptibility. Cefcanel inhibits 90% of S. aureus strains at 2 µg/ml, irrespective of the presence of a β-lactamase. Cefcanel 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
Disposition of oral [14C]cefcanel daloxate hydrochloride in healthy male subjects.
1993 Jan-Feb
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:11:08 GMT 2023
Edited
by admin
on Sat Dec 16 17:11:08 GMT 2023
Record UNII
2F5V2R6VX8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFCANEL
INN   WHO-DD  
INN  
Official Name English
cefcanel [INN]
Common Name English
(6R,7R)-7-((R)-MANDELAMIDO)-3-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Common Name English
Cefcanel [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76158
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
MESH
C022605
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
INN
6292
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID00866067
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
FDA UNII
2F5V2R6VX8
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
PUBCHEM
68666
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
EVMPD
SUB07381MIG
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908354
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
SMS_ID
100000081794
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
CAS
41952-52-7
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY