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Cefodizime

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Cefodizime Basic information

Product Name:
Cefodizime
Synonyms:
  • Cefodizim
  • CEFODIZIME
  • Cefodizime,CDZM
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-, (6R,7R)-
  • 7-(α-(Z)-Methoxyimino-α-(2-aminothiazol-4-yl)acetamido)-3-((5-carboxymethyl-4-methylthiazol-2-yl)thiomethyl)-3-cephem-4-carboxylic acid
  • 7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((5-(carboxymethyl)-4-methyl-2-thiazolyl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • FIR-221
  • Cefodizme
CAS:
69739-16-8
MF:
C20H20N6O7S4
MW:
584.67
EINECS:
1592732-453-0
Product Categories:
  • Pharmaceutical intermediate
Mol File:
69739-16-8.mol
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Cefodizime Chemical Properties

Melting point:
>170°C (dec.)
alpha 
D25 -55.9°
Density 
1.86±0.1 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
DMSO (Slightly), Methanol (Slightly, Heated)
form 
Solid
pka
pK1 2.85; pK2 3.37; pK3 4.18(at 25℃)
color 
White to Off-White
CAS DataBase Reference
69739-16-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-42/43
Safety Statements 
22-26-36/37/39
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Cefodizime Usage And Synthesis

Chemical Properties

Cefodizime Sodium is a white to light yellowish white crystalline powder. It has no odor or a slightly peculiar odor and has a bitter taste. It is highly soluble in water (around 270g/L) but only sparingly soluble in ethanol or ether.

Uses

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.

Definition

ChEBI: Cefodizime is a cephalosporin compound having 5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It has a role as an antibacterial drug and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a cephalosporin, a member of 1,3-thiazoles and an oxime O-ether.

Preparation

The synthesis of cefodizime involved the following steps:
Dissolve 6.1g of (2-mercapto-4-methylthiazol-5-yl) acetic acid in water and adjust the pH to 6.5 by adding 2 mol/L sodium hydroxide.
Heat the solution to 70°C and then add a solution of 12g of cefotaxime in 75ml of water with stirring.
Keep stirring the mixture at 70°C for 3 hours while maintaining the pH at 6.5 by adding 2 mol/L sodium hydroxide.
Cool the mixture to room temperature and acidify it to pH 2.8.
Filter the resulting precipitate and wash it with water.
Dry the precipitate under vacuum and in the presence of phosphorus pentoxide.
As a result, 10g of cefodizime is obtained.
Cefodizime, an aminothiazolylcephalosporin. V. Synthesis and structure-activity relationships in the cefodizime series. DOI: 10.7164/antibiotics.40.29

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