Penem

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Class of antibiotics

title: "Penem" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["beta-lactam-antibiotics"] description: "Class of antibiotics" topic_path: "general/beta-lactam-antibiotics" source: "https://en.wikipedia.org/wiki/Penem" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class of antibiotics ::

A penem is a type of β-lactam with an unsaturated five-member heterocycle containing a sulfur atom in a pentacyclic ring fused to the β-lactam ring. Penems do not occur naturally; all are synthetic.{{cite journal|journal=Antimicrobic Newsletter|title= The carbapenems and Penem Antibiotics—a brief review|author=Richard Wise|volume=7|issue= 10|year=1990|pages=73–78| doi=10.1016/0738-1751(90)90045-E}} Related to penems are carbapenems, which have a carbon atom in place of the sulfur atom.

An example is faropenem.

Structure

::figure[src="https://upload.wikimedia.org/wikipedia/commons/5/5a/Faropenem.svg" caption="pmid=17402834 }}"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/9/93/Imipenem.svg" caption="Imipenem, a [[carbapenem]]. Imipenem has a sulfur atom that is not in the pentacyclic ring."] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/a/ab/Penicillin-G.svg" caption="[[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.

Five main penem subgroups — thiopenems, oxypenems, aminopenems, alkylpenems, and arylpenems — have been produced and are distinguished by the side chain (at position 2) of the unsaturated five-membered ring. One structurally distinct penem is BRL 42715. This molecule has no substitution at the above position, but has a bulky group attached to the β-lactam ring, and it displays effective inhibition of class C β-lactamases, but no antimicrobial activity.

One possible consequence of these structural differences of penems from other β-lactams may be reduced immunogenicity and immunogenic cross-reactivity.

References

References

  1. "Medscape.com".
  2. (March 2003). "Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates". [[Journal of Antimicrobial Chemotherapy]].
  3. (2007). "Faropenem: Review of a new oral penem". Expert Review of Anti-Infective Therapy.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

beta-lactam-antibiotics