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Cefazedone

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Cefazedone Basic information

Product Name:
Cefazedone
Synonyms:
  • (6R,7R)-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-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
  • (6R-trans)-Cefazedone
  • Cefazedone acid
  • (6R,7R)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 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)-
  • (6r-trans)--8-oxo
  • 1(4h)-pyridinyl)acetyl)amino)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)
  • 7-(((3,5-dichloro-4-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicaci
CAS:
56187-47-4
MF:
C18H15Cl2N5O5S3
MW:
548.44
EINECS:
611-363-5
Product Categories:
  • Bases & Related Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Nucleotides
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
Mol File:
56187-47-4.mol
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Cefazedone Chemical Properties

Melting point:
157 - 160°C
Density 
1.78±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
2.61±0.50(Predicted)
form 
Solid
color 
White to Off-White
CAS DataBase Reference
56187-47-4(CAS DataBase Reference)
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Cefazedone Usage And Synthesis

Originator

Cefazedone Sodium,Arocor Holdings Inc.

Uses

Semi-synthetic cephalosporin antibiotic. Antibacterial.

Definition

ChEBI: A cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and [(3,5-dichloro-4-oxopyridin-1(4H)-yl)acetamido side-groups.

Manufacturing Process

A solution of 1 eq. of the tert-butyl ester of 7-aminocephalosporanic acid and 1 eq. of dicyclohexylcarbodiimide in 100 ml of methylene chloride/DMF (1:1) is cooled to 0°C. The mixture is combined with 1 eq. of 3,5-dichloro-4- pyridone-1-acetic acid; after 5 min the ice bath is removed and the mixture agitated for another 30 min at 25°C. The thus-formed urea is filtered off and the filtrate filtered over silica gel (eluent: ethyl acetate/1% methanol). The solvent is concentrated by evaporation, and the thus-obtained tert-butyl ester of 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid is crystallized from ether.
1 eq. of the tert-butyl ester is dissolved in 30 ml of trifluoroacetic acid. After 30 minutes, the solution is evaporated and the thus-produced 7-(3,5-dichloro- 1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid crystallized from ether.
1 eq. of the obtained 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido) cephalosporanic acid is dissolved in 60 ml of saturated aqueous sodium bicarbonate solution at a pH of below 7 and combined with 1 eq. of 5-methyl- 1,3,4-thiadiazole-2-thiol in 20 ml of acetone. The reaction solution is agitated for 2 hours at 80°C and at a pH of 6.3 under a nitrogen atmosphere. The acetone is thereupon removed, the solution is washed with ether and acidified to pH 2. The thus-obtained 3-(1-methyltetrazolyl-5-mercaptomethyl)-7-(3,5- dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)-3-cephem-4-carboxylic acid is filtered off and dried. IR spectrum confirmed the structure of cefazedone.
In practice it is usually used as sodium salt.

Therapeutic Function

Antibiotic

CefazedoneSupplier

Changzhou Red Sun Pharmaceutical Co., Ltd. Gold
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0519-85223897 13766960291
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Adamas Reagent, Ltd.
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BOC Sciences
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1-631-485-4226; 16314854226
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