Carbapenam

Carbapenam
Names
IUPAC name
1-Azabicyclo[3.2.0]heptan-7-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H9NO/c8-6-4-5-2-1-3-7(5)6/h5H,1-4H2
    Key: INAHHIFQCVEWPW-UHFFFAOYSA-N
  • InChI=1/C6H9NO/c8-6-4-5-2-1-3-7(5)6/h5H,1-4H2
    Key: INAHHIFQCVEWPW-UHFFFAOYAR
  • O=C1N2C(C1)CCC2
Properties
C6H9NO
Molar mass 111.144 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

A carbapenam is the parent member of the β-lactams compounds. The parent is of only of theoretical interest, but substituted derivatives are important carbapenem antibiotics, originally inspired by the structure of penicillin. In penicillin, the five-membered ring contains sulfur, whereas carbapenams have a CH2 in place of S. A related class of antibiotics are unsaturated carbapenems. Carbapenam-based antibiotics are widely used, but resistant strains of some pathogens have emerged.

Structure of (3S,5R)-carbapenam-3-carboxylic acid

References

  1. ↑ Dalhoff, A.; Janjic, N.; Echols, R. (2006). "Redefining penems". Biochemical Pharmacology. 71 (7): 1085–1095. doi:10.1016/j.bcp.2005.12.003. PMID 16413506.
  2. ↑ Chen, Ying; Fang, Li; Yang, Yunxing; Yan, Rushuang; Fu, Ying; Shen, Ping; Zhao, Dongdong; Chen, Yan; Hua, Xiaoting; Jiang, Yan; Moran, Robert A.; Van Schaik, Willem; Yu, Yunsong (2021). "Emergence of carbapenem-resistant Klebsiella pneumoniae harbouring bla OXA-48-like genes in China". Journal of Medical Microbiology. 70 (3). doi:10.1099/jmm.0.001306. PMC 8346730. PMID 33507142.