121020-94-8

Basic information

• Product Name: (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS NO: 121020-94-8
• Molecular Formula: C₁₄H₁₅N₅O₆S₂
• Molecular Weight: 413.4288
• Mol File: 121020-94-8.mol
• Article Data: 14

Chemical Properties

• Density: 1.922g/cm³
• Refractive Index: 1.843
• CAS DataBase Reference: (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(121020-94-8)
• EPA Substance Registry System: (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(121020-94-8)

Safety Data

• Hazardous Substances Data: 121020-94-8(Hazardous Substances Data)

Upstream product

• 137-42-8 sodium N-methyldithiocarbamate 
• 73384-59-5 Ceftriaxone 
• 63527-52-6 cefotaxime 
• 758680-79-4 cefotaxime 
• 86329-79-5 Kenicef 
• 60846-21-1 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid 
• 60846-23-3 cefotaxime sodium salt 

Downstream Products

• 112601-22-6 7β-[2-(2-aminothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-[(imidazo[1,2-a]pyridinium-1-yl)methyl]-3-cephem-4-carboxylate 
• 112601-22-6 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-(imidazo[1,2-a]pyridinium-1-yl)-methyl-3-cephem-4-carboxylate 

Relevant articles and documents

Kinetics and mechanism of degradation of cefotaxime sodium in aqueous solution

The degradation kinetics and mechanism of a potent new cephalosporin, cefotaxime sodium, in aqueous solution were investigated at pH 0-10 at 25° and an ionic strength of 0.5. The degradation rates were determined by high-pressure liquid chromatography and were observed to follow pseudo first-order kinetics with respect to cefotaxime sodium concentration. The data suggested that the rate of degradation was influenced significantly by solvolytic, hydrogen ion, and hydroxide ion catalysis. No primary salt effects were observed in the acid or neutral regions; however, a positive salt effect was observed at pH 8.94. Buffer catalysis due to the buffer species employed was not seen during the kinetic studies. The pH-rate profile at 25° indicated that the maximum stability of cefotaxime sodium occurred in the pH 4.5-6.5 region. In aqueous solution, cefotaxime was shown to degrade by two parallel reactions; de-esterification at the C-3 position and β-lactam cleavage. Good agreement between the the theoretical pH-rate profile and the experimental data support the proposed degradation process.

Controlled hydrolysis of ceftiofur sodium, a broad-spectrum cephalosporin; isolation and identification of hydrolysis products

Ceftiofur sodium is the salt of (6R,7R)-7-{[(2-amino-4-thiazoyl)-Z- (methoxyimino)acetyl]amino}-3-{[(2-furanylcarbonyl)thio]methyl}-8-oxo-5- thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. This compound is very susceptible to acid, alkaline-, and enzyme-catalyzed hydrolysis, producing a number of unstable degradation products. In this report, we describe the preparation and identification of the hydrolysis products that are formed under controlled alkaline conditions. The primary hydrolysis product was desfuroyl ceftiofur, which is the most abundant metabolite in bovine blood. Desfuroyl ceftiofur was carefully oxidized with H2O2 to prepare the disulfide dimer, a urinary metabolite of ceftiotur sodium in the rat and cattle. Under acidic conditions, desfuroyl ceftiofur was converted to the corresponding thiolactone. The preparation of desacetyl cefotaxime, which is the oxygen analog of desfuroyl ceftiofur, is also described. Furoic acid was readily formed by hydrolytic cleavage of the thioester bond. Thiofuroic acid, formed by the less common cleavage on the alkyl side of the thioester bond, was also isolated.

Cephem compounds, their production and use

This invention relates to a compound of the formula: STR1 wherein Q is nitrogen or CH; R1 is hydrogen or a lower alkyl group which may be substituted; and ring A is a pyridine or pyridazine ring which is substituted at the ring-constituting car