56842-77-4

Basic information

• Product Name: Cefazolin IMpurity C
• Synonyms: Cefazolin IMpurity C;(6R,7R)-3-methyl-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefazolin EP Impurity C;(6R,7R)-7-(2-(1H-tetrazol-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefazolin USP Impurity H
• CAS NO: 56842-77-4
• Molecular Formula: C₁₁H₁₂N₆O₄S
• Molecular Weight: 324.31578
• Mol File: 56842-77-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Sonicated), TFA (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Cefazolin IMpurity C(CAS DataBase Reference)
• NIST Chemistry Reference: Cefazolin IMpurity C(56842-77-4)
• EPA Substance Registry System: Cefazolin IMpurity C(56842-77-4)

Safety Data

• Hazardous Substances Data: 56842-77-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cefazolin IMpurity C is used as an impurity in the production of Cefazolin, a widely used semi-synthetic antibiotic with potent antibacterial properties. It is essential to monitor and control the levels of this impurity to ensure the safety, efficacy, and quality of the final antibiotic product.
Used in Research and Development:
Cefazolin IMpurity C serves as a valuable compound for researchers in the field of pharmaceuticals and medicinal chemistry. It can be used to study the structure-activity relationship of Cefazolin and its analogs, potentially leading to the development of new and improved antibiotics with enhanced properties.
Used in Quality Control and Regulatory Compliance:
Cefazolin IMpurity C is utilized in the quality control processes of pharmaceutical manufacturers to ensure that the final product meets the required standards and regulations. By analyzing and quantifying the presence of this impurity, manufacturers can maintain the safety and efficacy of Cefazolin and comply with regulatory guidelines.
Used in Drug Interaction Studies:
Cefazolin IMpurity C can be employed in drug interaction studies to investigate potential side effects, toxicity, and synergistic effects when Cefazolin is administered in combination with other medications. This information is crucial for the development of safe and effective drug regimens for patients.

Upstream product

• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 55633-19-7 (1H-tetrazol-1-yl)-2-acetic acid methyl ester 

Relevant articles and documents

Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid

The influence of the substrate structure on the catalytic properties of penicillin G acylase (PGA) from Escherichia coli in kinetically controlled acylations has been studied. In particular, the affinity of different β-lactam nuclei towards the active site has been evaluated considering the ratio between the rate of synthesis (vs) and the rate of hydrolysis of the acylating ester (vhl). 7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-(1-sulfomethyl-1,2,3,4-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (7-SACA) showed a good affinity for the active centre of PGA. The enzymatic acylation of these nuclei with R-methyl mandelate has been studied in order to evaluate different approaches for the enzymatic synthesis of cefonicid. The best results have been obtained in the acylation of 7-SACA. Cefonicid (8) was recovered from the reaction mixture as the disodium salt in 65% yield and about 95% of purity. Furthermore, through acylation of 7-ACA, a "one-pot" chemo-enzymatic synthesis was carried out starting from cephalosporin C using three enzymes in sequence: D-amino acid oxidase (DAO), glutaryl acylase (GA) and PGA. Cefonicid disodium salt was obtained in three steps, avoiding any intermediate purification, in 35% overall yield and about 94% purity. This approach presents several advantages compared with the classical chemical processes.