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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19N3O6S
Molecular Weight 405.425
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALOGLYCIN ANHYDROUS

SMILES

CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C2=O)C(O)=O

InChI

InChIKey=FUBBGQLTSCSAON-PBFPGSCMSA-N
InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1

HIDE SMILES / InChI

Description

Cephaloglycin, first oral cephalosporin, was introduced in 1965, but is no longer in common use. It is an orally absorbed derivative of cephalosporin C. Cephaloglycin 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.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
KAFOCIN
PMID

PMID

TitleDatePMID
Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin.
1989 Mar 1
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
1990
The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem.
1990 Nov
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.
1996 Jul-Aug
Plasma glutathione peroxidase and its relationship to renal proximal tubule function.
1998 Nov
Treating critical illness: the importance of first doing no harm.
2005 Jun
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.
2008 Sep 10
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.
2010
Protein engineering of penicillin acylase.
2010 Jul
Patent

Patent

Sample Use Guides

In Vivo Use Guide
Each subject received a single oral dose of each of the following: 250, 500, and 1,000 mg of cephaloglycin after an overnight fast
Route of Administration: Oral
In Vitro Use Guide
M. hyorhinis strains were susceptible to cephaloglycin (MIC = 4.1 ug/ml)
Name Type Language
CEPHALOGLYCIN ANHYDROUS
Common Name English
CEFALOGLYCIN [WHO-DD]
Common Name English
CEFALOGLYCIN [JAN]
Common Name English
CEPHALOGLYCIN [MI]
Common Name English
CEFALOGLYCIN
INN   JAN   WHO-DD  
INN  
Official Name English
CEFALOGLYCIN [INN]
Common Name English
(6R,7R)-7-((R)-2-AMINO-2-PHENYLACETAMIDO)-3-(HYDROXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID ACETATE (ESTER)
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((AMINOPHENYLACETYL)AMINO)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))
Common Name English
CEPHALOGLYCIN [HSDB]
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL1200971
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
ECHA (EC/EINECS)
222-696-7
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
WIKIPEDIA
CEFALOGLYCIN
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
MERCK INDEX
M1064
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY Merck Index
EPA CompTox
3577-01-3
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
DRUG BANK
DB00689
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
PUBCHEM
19150
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY SWITZERF
HSDB
3577-01-3
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
CAS
3577-01-3
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
INN
1999
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
NCI_THESAURUS
C76593
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY
EVMPD
SUB06166MIG
Created by admin on Tue Mar 06 12:08:35 UTC 2018 , Edited by admin on Tue Mar 06 12:08:35 UTC 2018
PRIMARY