Penam

Penam
Names
IUPAC name
(5R)-4-thia-1-azabicyclo[3.2.0]heptan-7-one
Other names
1-Aza-7-oxo-4-thiabicyclo[3.2.0]heptane
Identifiers
3D model (JSmol)
4374479
ChEBI
ChemSpider
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
  • InChI=1S/C5H7NOS/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2/t5-/m1/s1
    Key: WSHJJCPTKWSMRR-RXMQYKEDSA-N
  • C1CSC2N1C(=O)C2
Properties
C5H7NOS
Molar mass 129.18 g·mol−1
Related compounds
Related compounds
 clavam
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Benzylpenicillin, an example of a penam
Not to be confused with penem.

Penams are the primary skeleton structures that define the penicillin subclass of the broader β-lactam family of antibiotics and related compounds. They are bicyclic ring systems containing a β-lactam moiety fused with a five-member thiazolidine ring. [1] Due to ring strain and limitations on amide resonance, the structure is unstable and highly susceptible to catalytic cleavage at the amide bond.[2] Benzylpenicillin (penicillin G) is the natural product parent that contains the penam structure.

  1. ^ Novak, Igor; Chua, Pei Juan (2006-09-01). "Computational Study of Pharmacophores: β-Lactams". The Journal of Physical Chemistry A. 110 (35): 10521–10524. Bibcode:2006JPCA..11010521N. doi:10.1021/jp063162b. ISSN 1089-5639. PMID 16942059.
  2. ^ Patrick, Graham (2017-03-23), "5. Pharmaceuticals and medicinal chemistry", Organic Chemistry: A Very Short Introduction, Oxford University Press, pp. 71–89, doi:10.1093/actrade/9780198759775.003.0005, ISBN 978-0-19-875977-5