1150883-75-2

Usage

Uses

Used in Pharmaceutical Industry:
(αS,2S,3R)-5-Carboxy-4-[[(3S,5S)-5-[[(3-carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4-dihydro-α-[(1R)-1-hydroxyethyl]-3-methyl-2H-pyrrole-2-acetic Acid is used as an impurity in the production of Ertapenem (E635000) for the pharmaceutical industry. Ertapenem is a broad-spectrum antibiotic used to treat various bacterial infections. The presence of (αS,2S,3R)-5-Carboxy-4-[[(3S,5S)-5-[[(3-carboxyphenyl)aMino]carbonyl]-3-pyrrolidinyl]thio]-3,4-dihydro-α-[(1R)-1-hydroxyethyl]-3-Methyl-2H-pyrrole-2-acetic Acid as an impurity may affect the efficacy, safety, or quality of the final product, making it crucial to monitor and control its levels during the manufacturing process.

Upstream product

• 153832-46-3 ertapenem 

Relevant academic research and scientific papers

A New Mechanism for β-Lactamases: Class D Enzymes Degrade 1β-Methyl Carbapenems through Lactone Formation

β-Lactamases threaten the clinical use of carbapenems, which are considered antibiotics of last resort. The classical mechanism of serine carbapenemase catalysis proceeds through hydrolysis of an acyl-enzyme intermediate. We show that class D β-lactamases also degrade clinically used 1β-methyl-substituted carbapenems through the unprecedented formation of a carbapenem-derived β-lactone. β-Lactone formation results from nucleophilic attack of the carbapenem hydroxyethyl side chain on the ester carbonyl of the acyl-enzyme intermediate. The carbapenem-derived lactone products inhibit both serine β-lactamases (particularly class D) and metallo-β-lactamases. These results define a new mechanism for the class D carbapenemases, in which a hydrolytic water molecule is not required.

?-LACTONE COMPOUNDS

The present invention relates to certain β-lactone compounds that may be useful as inhibitors of bacterial beta-lactamases. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising t