Cefodizime

Cefodizime is a third generation cephalosporin antibiotic with a broad spectrum of antibacterial activity. Cefodizime has no renal toxic effect, good tolerance and immune regulation activity, and is widely used in the treatment of severe infections of the respiratory and urinary tracts[1][2].

Method 1: Use cefotaxime as raw material. 6.1g (2-mercapto-4-methylthiazol-5-yl)acetic acid was dissolved in water, adjusted to Ph value 6.5 with 2mol/L, sodium hydroxide. Heat to 70°C and add a solution of 12g of cefotaxime in 75ml of water with stirring. Stirring was continued for 3h at 70°C, and the Ph value was kept at 6.5 by adding 2mol/L sodium hydroxide. Cool to room temperature and acidify to Ph=2.8. The filtered precipitate was washed with water and dried in the presence of vacuum and phosphorus pentoxide to obtain 10 g of cefodizime. Method 2: Use 7-ACA as raw material. 10g 7-ACA tosylate and 4.7g (2-mercapto-4-methylthiazol-5-yl)acetic acid were suspended in 200ml of water, and the Ph value was adjusted to 6.5-6.8 with 1mol/L sodium hydroxide. Stir at 60°C for 3h, and keep Ph value 6.5 ~ 6.8. After cooling to room temperature, the reaction solution was shaken with ethyl acetate three times, and the ethyl acetate was discarded each time. The water layer was acidified with 2mol/L hydrochloric acid to Ph=4.0. The precipitate was removed by filtration, and the precipitate was washed with water. The washing liquid and the filtrate are combined and stirred with 200 ml of acetone. The precipitate was collected by filtration, washed with acetone, and dried in vacuo to obtain 6.7 g of compound (I). 7.54g 2-(Z)-methoxyimino-2-(2-aminothiazol-4-yl)acetic acid was dissolved in 100ml of dimethylformamide, and 5.7g of 1-hydroxybenzotriazole-hydrate (HOBT) was added ?H2O) and 8.5g of dicyclohexylcarbodiimide (DCCI), after stirring at room temperature for 4h, the resulting dicyclohexylurea was removed by filtration. 15g of finely ground compound (I) was added and stirring was continued for 18h. After the reaction solution was filtered, 380 ml of water was added. The precipitate was removed by filtration, and 450 ml of water was added to the filtrate. The crystals were collected by filtration and washed with water to obtain 6 g of cefodizime.

Cefodizime is a third generation cephalosporin with a broad spectrum of antibacterial activity. Cefodizime maybe useful in the treatment of otitis media, sinusitis and gynaecological infections, and for the prophylaxis or treatment of surgical infections.

Molecular Weight:584.7
XLogP3:0.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:10
Exact Mass:584.02763169
Monoisotopic Mass:584.02763169
Topological Polar Surface Area:305
Heavy Atom Count:37
Complexity:1030
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes