CEFAZEDONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H15Cl2N5O5S3
Molecular Weight	548.443
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC3=NN=C(C)S3)=C(N1C(=O)[C@H]2NC(=O)CN4C=C(Cl)C(=O)C(Cl)=C4)C(O)=O

InChI

InChIKey=VTLCNEGVSVJLDN-MLGOLLRUSA-N

InChI=1S/C18H15Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h2-3,12,16H,4-6H2,1H3,(H,21,26)(H,29,30)/t12-,16-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C76157 | https://www.ncbi.nlm.nih.gov/pubmed/39575

Cefazedone is a semisynthetic first-generation cephalosporin with activity against Gram-positive and Gram-negative bacteria. Cefazedone 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. Unlike other cephalosporins cefazedone possesses good activity against gram-positive bacteria

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Penicillin-binding protein 31 Target ID: CHEMBL2362973 Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C76157	Inhibitor 8297

PubMed

Title	Date	PubMed
The hematologic effects of cefonicid and cefazedone in the dog: a potential model of cephalosporin hematotoxicity in man.	1987 Aug	3629586
A case of postoperative tuberculous spondylitis with a bizarre course.	2009 Mar	19884999
Investigation of the toxic functional group of cephalosporins by zebrafish embryo toxicity test.	2010 Oct	20938949

Patents

Sample Use Guides

In Vivo Use Guide

The doses were: i.v. cefazedone 500 mg and 1000 mg; cefazolin 1000 mg; i.m. cefazedone 500 mg, cefazolin 500 mg.

Route of Administration: Parenteral

In Vitro Use Guide

The sensitivity of 67 strains of Neisseria gonorrhoeae isolated from 1977 to 1978 were tested against cefazedone (Refosporen). All strains including three penicillin-resistant beta-lactamase producing Neisseria were sensitive at a range of 0.0078 to 2.0 ug/ml cefazedone.

Name

Type

Language

CEFAZEDONE

Official Name

English

Cefazedone [WHO-DD]

Common Name

English

CEFAZEDONE [MI]

Common Name

English

cefazedone [INN]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((2-(3,5-DICHLORO-4-OXO-1(4H)-PYRIDINYL)ACETYL)AMINO)-3-(((5-METHYL-1,3,4-THIADIAZOL-2-YL)THIO)METHYL)-8-OXO-, (6R,7R)-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

J01DB06