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
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
Molecular Formula | C18H19N3O6S |
Molecular Weight | 405.425 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4887297/ |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALOGLYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4887297/ |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALOGLYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4887297/ |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALOGLYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
75% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4887297/ |
0.5 g single, oral dose: 0.5 g route of administration: Oral experiment type: SINGLE co-administered: |
CEPHALOGLYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4385749
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/697348
Curator's Comment: All strains of group A streptococci
(Streptococcus pyogenes) and Diplococcus pneumoniae were inhibited by 0.4
ug of cephaloglycin per ml. https://www.ncbi.nlm.nih.gov/pubmed/4385749
M. hyorhinis strains were susceptible to cephaloglycin (MIC = 4.1 ug/ml)
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:17:02 GMT 2023
by
admin
on
Fri Dec 15 16:17:02 GMT 2023
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Record UNII |
HD2D469W6U
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C357
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CHEMBL1200971
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572
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222-696-7
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CEFALOGLYCIN
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m1064
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DB00689
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19150
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100000081376
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3577-01-3
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1999
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C76593
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SUB06166MIG
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS | |||
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SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
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ACTIVE MOIETY |