Cefazedone

Base Information

• Chemical Name: Cefazedone
• CAS No.: 56187-47-4
• Molecular Formula: C18H15Cl2N5O5S3
• Molecular Weight: 548.452
• European Community (EC) Number: 611-363-5
• UNII: 7Y86X0D799
• DSSTox Substance ID: DTXSID50204733
• Nikkaji Number: J11.127I
• Wikipedia: Cefazedone
• Wikidata: Q5057222
• NCI Thesaurus Code: C76157
• Metabolomics Workbench ID: 154558
• ChEMBL ID: CHEMBL2107636
• Mol file: 56187-47-4.mol

Synonyms:7-(2-(3,5-dichloro-4-oxo-1- pyridyl)acetamido)-3-(5-methyl-1,3,4-thiadiazol- 2-ylthiomethyl)-3-cephem-4-carboxylic acid;cefazedone;cefazedone sodium;cefazedone, monosodium salt;EMD 30 087;EMD30087;Refosporen;Refosporin

Chemical Property of Cefazedone

Chemical Property:

• Appearance/Colour: White to yellowish white powder
• Refractive Index: 1.719
• PKA: 2.61±0.50(Predicted)
• PSA: 213.33000
• Density: 1.78 g/cm³
• LogP: 2.17470
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 546.9612375
• Heavy Atom Count: 33
• Complexity: 984

Purity/Quality:

99% ^*data from raw suppliers

Cefazedone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=C(C(=O)C(=C4)Cl)Cl)SC2)C(=O)O
• Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=C(C(=O)C(=C4)Cl)Cl)SC2)C(=O)O
• Uses: Semi-synthetic cephalosporin antibiotic. Antibacterial.
• Therapeutic Function: Antibiotic

Technology Process of Cefazedone

There total 7 articles about Cefazedone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

C12H13Cl2NO4 + C11H12N4O3S3*ClH → cefazedone (56187-47-4)

Guidance literature:

With triethylamine; In acetonitrile; at 0 - 5 ℃; for 0.5h; pH=6.8;

Reference yield: 93.86%

C15H12BrCl2N3O5S + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → cefazedone (56187-47-4)

Guidance literature:

With triethylamine; In ethanol; for 10h; Solvent; Reagent/catalyst; Reflux;

Reference yield: 93.0%

2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid (56187-37-2) + (6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (30246-33-4) → cefazedone (56187-47-4)

Guidance literature:

With ortho-iodophenylboronic acid; In toluene; Solvent; Reflux;

upstream raw materials:

2-(3,5-dichloro-4-oxopyridine-1(4H)-yl)acetic acid

(6R,7R)-7-amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3-deacetyloxy-7-aminocephalosporanic acid

2-mercapto-5-methyl-1,3,4-thiadiazole

Downstream raw materials:

(6R,7R)-3-[[(5-methyl-1,3,4-thiadiazolyl-2-yl)thio]methyl]-7-[2-(3,5-dichloro-4-pyridone-1-acetylamido)]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt

Refernces

• 1、 -. "Synthesis technology of cefazedone". . . Retrieved 2019/11/21.
• 2、 Gericke,Rogalski. "New 4-pyridonyl-acetamido-cephalosporins and related compounds". . p. 362 - 369. Retrieved 2007/10/08.