CEPHALOGLYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H19N3O6S.2H2O
Molecular Weight	441.456
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.[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=KURFSUDYQUKEJZ-SBMYYUOMSA-N

InChI=1S/C18H19N3O6S.2H2O/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);2*1H2/t12-,13-,17-;;/m1../s1

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00689 | https://ncit.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI%20Thesaurus&code=C65307 | https://www.ncbi.nlm.nih.gov/pubmed/7380734

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 Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.drugbank.ca/drugs/DB00689 \| https://www.ncbi.nlm.nih.gov/pubmed/7565098 \| https://ncit.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI%20Thesaurus&code=C65307 \| http://www.genome.jp/dbget-bin/www_bget?D01949	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4385749	Curative		Approved 8429	KAFOCIN Approved Use For treatment of severe infections caused by susceptible bacteria. Launch Date 1970

C_max

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

T_1/2

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

F_unbound

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCTN2 66

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 71	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00689, https://pubmed.ncbi.nlm.nih.gov/10525100/	no

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2DJO
ABI Chem	AC1Q6LOC
AN PharmaTech	AN-5594
AmicBase - Antimicrobial Activities	6135
BOC Sciences	612516
Chem Scene	CS-0006156	http://www.chemscene.com/3577-01-3.html
ChemMol	49400347	http://www.chemmol.com/chemmol/49400347.html
Chemieliva Pharmaceutical Co., Ltd	PBCM1043569
Compound Cloud	166592
Compound Cloud	19150
Glentham Life Sciences	GA2220	http://www.glentham.com/products/product/GA2220/
MedChem Express	HY-16137	https://www.medchemexpress.com/cefaloglycin.html
MuseChem	I005917	https://www.musechem.com/product/I005917.html
NovoSeek	19150
Smolecule	S793587	https://www.smolecule.com/products/s793587
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0143
ZINC	ZINC000003830503	http://zinc15.docking.org/substances/ZINC000003830503
eMolecules	107055846
eMolecules	110034559
eNovation Chemicals	D673812	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673812

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	2930580
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Plasma glutathione peroxidase and its relationship to renal proximal tubule function.	1998 Nov	9851889
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.	2008 Sep 10	18602240
Protein engineering of penicillin acylase.	2010 Jul	22649651

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)

Name

Type

Language

CEPHALOGLYCIN

Official Name

English

39435

Code

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*))), DIHYDRATE

Common Name

English

KEFOCIN

Brand Name

English

7-(D-.ALPHA.-AMINOPHENYLACETAMIDO)-CEPHALOSPORANIC ACID DIHYDRATE

Common Name

English

CEPHALOGLYCIN [ORANGE BOOK]

Common Name

English

CEFALOGLYCIN DIHYDRATE

Common Name

English

CEPHALOGLYCIN [USAN]

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) dihydrate

Common Name

English

KAFOCIN

Brand Name

English

CEPHALOGLYCIN DIHYDRATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357