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词条 Penem
释义

  1. Structure

  2. References

  3. Further reading

{{distinguish|penam}}

A penem is a type of unsaturated β-lactam with a sulfur atom in the five-membered ring. Penems do not occur naturally; all are synthetic.[1] Related to penems are carbapenems. Where penems have a sulfur, carbapenems have another carbon.[2]

An example is faropenem.[3]

Structure

{{See also|Beta-lactam#Nomenclature|l1=β-Lactam nomenclature}}

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

1. ^{{cite journal|journal=Antimicrobic Newsletter|title=The carbapenems and Penem Antibiotics—a brief review|author=Richard Wise|volume=7|year=1990|pages=73-78|doi=10.1016/0738-1751(90)90045-E}}
2. ^{{cite web |url=http://www.medscape.com/viewarticle/464632_2 |title=Medscape.com |website= |accessdate=}}
3. ^{{cite journal |vauthors=Milazzo I, Blandino G, Caccamo F, Musumeci R, Nicoletti G, Speciale A |title=Faropenem, a new oral penem: antibacterial activity against selected anaerobic and fastidious periodontal isolates |journal=Journal of Antimicrobial Chemotherapy |volume=51 |issue=3 |pages=721–5 |date=March 2003 |pmid=12615878 |doi= 10.1093/jac/dkg120|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12615878}}

Further reading

  • {{cite journal |vauthors=Sasaki A, Goda K, Enomoto M, Sunagawa M |title=Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by (2 + 2) cycloaddition of diketene and Schiff bases |journal=Chemical & Pharmaceutical Bulletin |volume=40 |issue=5 |pages=1094–7 |date=May 1992 |pmid=1394625 |doi= 10.1248/cpb.40.1094|url=}}
{{Cell wall disruptive antibiotics}}

1 : Beta-lactam antibiotics

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