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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 |  |
| | 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) |
| | 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 |
| | Cefazedone Preparation Products And Raw materials |
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