U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H14Cl2N5O5S3.Na
Molecular Weight 570.425
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFAZEDONE SODIUM

SMILES

[Na+].[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=KPHCAENKLGZHCB-VQZRABBESA-M
InChI=1S/C18H15Cl2N5O5S3.Na/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);/q;+1/p-1/t12-,16-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H14Cl2N5O5S3
Molecular Weight 547.435
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Approval Year

PubMed

PubMed

TitleDatePubMed
The hematologic effects of cefonicid and cefazedone in the dog: a potential model of cephalosporin hematotoxicity in man.
1987 Aug
A case of postoperative tuberculous spondylitis with a bizarre course.
2009 Mar
A case of famotidine-induced anaphylaxis.
2010
Investigation of the toxic functional group of cephalosporins by zebrafish embryo toxicity test.
2010 Oct
Determination of cefazedone in human plasma by high performance liquid chromatography-tandem mass spectrometry: Application to a pharmacokinetic study on Chinese volunteers.
2010 Oct 15
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:36:59 GMT 2023
Edited
by admin
on Fri Dec 15 17:36:59 GMT 2023
Record UNII
658X66LF6Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFAZEDONE SODIUM
MART.   WHO-DD  
Common Name English
NSC-304118
Code English
Cefazedone sodium [WHO-DD]
Common Name English
CEFAZEDONE SODIUM SALT
MI  
Common Name English
CEFAZEDONE SODIUM [MART.]
Common Name English
CEFAZEDONE SODIUM SALT [MI]
Common Name English
REFOSPORIN
Common Name English
SODIUM (7R)-7-(2-(3,5-DICHLORO-4-OXO-1-PYRIDYL)ACETAMIDO)-3-(5-METHYL-1,3,4-THIADIAZOL-2-YLTHIOMETHYL)-3-CEPHEM-4-CARBOXYLATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
Code System Code Type Description
EVMPD
SUB01106MIG
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
NCI_THESAURUS
C98216
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID70212931
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
PUBCHEM
23673603
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-293-9
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
FDA UNII
658X66LF6Y
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
SMS_ID
100000084962
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
MERCK INDEX
m1059
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY Merck Index
CAS
63521-15-3
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
NSC
304118
Created by admin on Fri Dec 15 17:36:59 GMT 2023 , Edited by admin on Fri Dec 15 17:36:59 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY