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Backbone structure of a carbapenem. Carbapenems are a class of very effective antibiotic agents most commonly used for treatment of severe bacterial infections.This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections.
β-Lactam antibiotics (beta-lactam antibiotics) are antibiotics that contain a β-lactam ring in their chemical structure. This includes penicillin derivatives ( penams ), cephalosporins and cephamycins ( cephems ), monobactams , carbapenems [ 1 ] and carbacephems . [ 2 ]
Imipenem, a carbapenem. Imipenem has a sulfur atom that is not in the pentacyclic ring. Benzylpenicillin, a penicillin. The double bond is absent in the pentacyclic ring. Penem molecules do not occur naturally, and production of penems is an entirely synthetic process.
The β-lactam core structures. (A) A penam.(B) A carbapenam.(C) An oxapenam.(D) A penem.(E) A carbapenem.(F) A monobactam.(G) A cephem.(H) A carbacephem.(I) An oxacephem. This is a list of common β-lactam antibiotics—both administered drugs and those not in clinical use—organized by structural class.
Penicillin core structure. The β-lactam ring is part of the core structure of several antibiotic families, the principal ones being the penicillins, cephalosporins, carbapenems, and monobactams, which are, therefore, also called β-lactam antibiotics. Nearly all of these antibiotics work by inhibiting bacterial cell wall biosynthesis.
Thienamycin was the first among the naturally occurring class of carbapenem antibiotics to be discovered and isolated. [3] Carbapenems are similar in structure to their antibiotic “cousins” the penicillins. Like penicillins, carbapenems contain a β-lactam ring (cyclic amide) fused to a five-membered ring. Carbapenems differ in structure ...
The structure is locked in a puckered (i.e. bent) shape due to the pyramidal geometry of the bridgehead nitrogen. The pyramidalization (χ = 54°) and twist of the C-N bond (τ = 18°) is caused by the strain from the lone pair's exclusion from planarity with the cyclic rings and electrostatic repulsion effects.
Structure of the carbapenem backbone. Carbapenems are a class of beta-lactam antibiotics that are capable of killing most bacteria by inhibiting the synthesis of one of their cell wall layers. The carbapenems were developed to overcome antibiotic resistance mediated by bacterial beta-lactamase enzymes.