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ChemicalBook--->CAS DataBase List--->56187-47-4

56187-47-4

56187-47-4 Structure

56187-47-4 Structure
IdentificationMore
[Name]

Cefazedone
[CAS]

56187-47-4
[Synonyms]

CEFAZEDONE SODIUM
REFOSPORIN
SODIUM-7-[3,5-DICHLORO-4-DIHYDROPYRIDYLACETYLAMINO]-3-[[(5-METHYL-1,3,4-THIADIAZOLYL)-THIO]METHYL]-3-CEPHEM-4-CARBOXYLATE
(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
cefazedone
REFOSPORIN[SODIUM-7-[3,5-DICHLORO-4-DIHYDROPYRIDYLACETYLAMINO]-3-[[(5-METHYL-1,3,4-THIADIAZOLYL)-THIO]METHYL]-3-CEPHEM-4-CARBOXYLATE]
(6R,7R)-7-(2-(3,5-Dichloro-4-oxo-1(4H)-pyridyl)acetamido)-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,7R)-7-[(3,5-Dichloro-4-oxo-1(4H)-pyridyl)acetylamino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]octan-2-ene-2-carboxylic acid
(6R,7R)-7-[2-(3,5-Dichloro-4-oxo-1(4H)-pyridyl)acetylamino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Refosporen
[EINECS(EC#)]

611-363-5
[Molecular Formula]

C18H14Cl2N5NaO5S3
[MDL Number]

MFCD01682029
[Molecular Weight]

570.43
[MOL File]

56187-47-4.mol
Chemical PropertiesBack Directory
[Melting point ]

157 - 160°C
[density ]

1.78±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

2.61±0.50(Predicted)
[color ]

White to Off-White
[CAS DataBase Reference]

56187-47-4(CAS DataBase Reference)
Hazard InformationBack Directory
[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
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