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Cefluprenam

From Wikipedia, the free encyclopedia
Cefluprenam
Names
IUPAC name
(6R,7R)-3-[(E)-3-[(2-amino-2-oxoethyl)-ethyl-methylazaniumyl]prop-1-enyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Other names
Antibiotic E 1077
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1 ☒N
    Key: XAKKNLNAJBNLPC-MAYKBZFQSA-N ☒N
  • InChI=1/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1
    Key: XAKKNLNAJBNLPC-MAYKBZFQBE
  • O=C2N1/C(=C(/C=C/C[N+](CC(=O)N)(CC)C)CS[C@@H]1[C@@H]2NC(=O)C(=N\OCF)/c3nc(sn3)N)C([O-])=O
Properties
C20H25FN8O6S2
Molar mass556.59 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Cefluprenam is a fourth generationcephalosporin.[1] It was patented in 2008 by now defunctCubist Pharmaceuticals.[2] A 1997 clinical trial illustrated that Cefluprenam is highly effective against bacterial pneumonia.[3]

References

[edit]
  1. ^PubChem."Cefluprenam".pubchem.ncbi.nlm.nih.gov. Retrieved2022-08-03.
  2. ^EU patent 2379580B1, Pearson, Lee Andre; Metcalf, A. Chester & Li, Jing, "Novel antibacterial agents for the treatment of gram positive infections", published 2011-10-26, issued 2013-10-23 
  3. ^Shimada, K.; Ohmichi, M.; Sasaki, H.; Watanabe, A.; Sato, K.; Nagai, K.; Konishi, K.; Ohta, T.; Matsuura, Y.; Ikeda, H.; Igarashi, K. (August 1997)."[Usefulness of 7 day therapy with cefluprenam in the management of respiratory tract infections]".Kansenshogaku Zasshi. The Journal of the Japanese Association for Infectious Diseases.71 (8):770–787.doi:10.11150/kansenshogakuzasshi1970.71.770.ISSN 0387-5911.PMID 9311195.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
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  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other


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