Carbapenam

Carbapenam
Names
	IUPAC name 1-Azabicyclo[3.2.0]heptan-7-one
Identifiers
CAS Number	23806-36-2 ; 73429-58-0 (R) ; 67506-08-5 (S) ;
3D model (JSmol)	Interactive image;
ChemSpider	477976;
PubChem CID	549337;
UNII	3S6CW82TW8;
CompTox Dashboard (EPA)	DTXSID10338487 ;
	InChI 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;
	SMILES O=C1N2C(C1)CCC2;
Properties
Chemical formula	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). Infobox references

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.^[1] Carbapenam-based antibiotics are widely used, but resistant strains of some pathogens have emerged.^[2]

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

References

^ 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.
^ 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.

[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.

[1]

[2]