CEPHALOGLYCIN MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H19N3O6S.H2O
Molecular Weight	423.44
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=FFOHOZBDRVVZIM-PFBPGKLMSA-N

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

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

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 1.39968E10

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
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.	1990	2083978
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

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 Created by `admin` on `Fri Dec 15 15:08:11 UTC 2023` Edited by `admin` on `Fri Dec 15 15:08:11 UTC 2023`
Record UNII	KR2KCF5IBM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CEPHALOGLYCIN MONOHYDRATE

Common Name

English

CEPHALOGLYCIN HYDRATE

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((AMINOPHENYLACETYL)AMINO)-8-OXO-, MONOHYDRATE, (6R-(6.ALPHA.,7.BETA.(R*)))-

Systematic Name

English

Code System Code Type Description

PUBCHEM

70610481

Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023

PRIMARY

FDA UNII

KR2KCF5IBM

Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023

PRIMARY

DRUG BANK

DBSALT001840

Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023

PRIMARY

CAS

22202-76-2

Created by admin on Fri Dec 15 15:08:11 UTC 2023 , Edited by admin on Fri Dec 15 15:08:11 UTC 2023

PRIMARY

Related Record Type Details


					HD2D469W6U

CEPHALOGLYCIN ANHYDROUS

ANHYDROUS->SOLVATE

Related Record Type Details


					HD2D469W6U

CEPHALOGLYCIN ANHYDROUS

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: 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

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator