Cefazedone
- CAS NO.:56187-47-4
- Empirical Formula: C18H15Cl2N5O5S3
- Molecular Weight: 548.44
- MDL number: MFCD00864865
- EINECS: 611-363-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-13 17:19:14
What is Cefazedone?
Originator
Cefazedone Sodium,Arocor Holdings Inc.
The Uses of Cefazedone
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
Properties of Cefazedone
Melting point: | 157 - 160°C |
Density | 1.78±0.1 g/cm3(Predicted) |
storage temp. | 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) |
Safety information for Cefazedone
Computed Descriptors for Cefazedone
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