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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

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

Molecular Formula C18H19N3O6S
Molecular Weight 405.425
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

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KAFOCIN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.8 μg/mL
0.5 g single, oral
CEPHALOGLYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3 μg × h/mL
0.5 g single, oral
CEPHALOGLYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
0.5 g single, oral
CEPHALOGLYCIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
75%
0.5 g single, oral
CEPHALOGLYCIN plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Sourcing

PubMed

Patents

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)
Substance Class Chemical
Record UNII
HD2D469W6U
Record Status Validated (UNII)
Record Version