Iboxamycin

Iboxamycin
Names
IUPAC name
(4S,5aS,8S,8aR)-N-{(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-4-(2-methylpropyl)-3,4,5,5a,6,7,8,8a-octahydro-2H-oxepino[2,3-c]pyrrole-8-carboxamide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H39ClN2O6S/c1-10(2)7-12-5-6-30-19-13(8-12)9-24-15(19)21(29)25-14(11(3)23)20-17(27)16(26)18(28)22(31-20)32-4/h10-20,22,24,26-28H,5-9H2,1-4H3,(H,25,29)/t11-,12-,13-,14+,15-,16-,17+,18+,19+,20+,22+/m0/s1
    Key: JPCLUJPDWMBCAA-SUTQZAMLSA-N
  • C[C@@H]([C@H]([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)SC)O)O)O)NC(=O)[C@@H]2[C@H]3[C@@H](C[C@@H](CCO3)CC(C)C)CN2)Cl
Properties
C22H39ClN2O6S
Molar mass 495.07 g·mol−1
Related compounds
Related compounds
 Cresomycin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Iboxamycin is a synthetic lincosamide or oxepanoprolinamide antibiotic. It binds to the bacterial ribosome in both Gram-negative and Gram-positive bacteria and it has been found to effective against bacteria which are resistant to other antibiotics that target the large ribosomal subunit. It was developed by combining an oxepanoproline unit with the aminooctose residue of clindamycin.[1]

Iboxamycin is effective against ESKAPE bacteria, methicillin-resistant Staphylococcus aureus (MRSA), Enterococcus, Clostridioides difficile,[1] and Listeria monocytogenes,[2] indicating an extended spectrum when compared to clindamycin.[1] Isotopic labeling of iboxamycin with tritium indicated that it binds 70 times more tightly to the ribosome than clindamycin.[3]

Iboxamycin can be administered orally and is safe when administered to mice.[1] It is a bacteriostatic antibiotic.[1]

See also

  • Cresomycin - a similar antibiotic developed from iboxamycin

References

  1. ^ a b c d e Mitcheltree, Matthew J.; Pisipati, Amarnath; Syroegin, Egor A.; Silvestre, Katherine J.; Klepacki, Dorota; Mason, Jeremy D.; Terwilliger, Daniel W.; Testolin, Giambattista; Pote, Aditya R.; Wu, Kelvin J. Y.; Ladley, Richard Porter; Chatman, Kelly; Mankin, Alexander S.; Polikanov, Yury S.; Myers, Andrew G. (2021). "A synthetic antibiotic class overcoming bacterial multidrug resistance". Nature. 599 (7885): 507–512. Bibcode:2021Natur.599..507M. doi:10.1038/s41586-021-04045-6. ISSN 0028-0836. PMC 8549432. PMID 34707295.
  2. ^ Brodiazhenko, Tetiana; Turnbull, Kathryn Jane; Wu, Kelvin J Y; Takada, Hiraku; Tresco, Ben I C; Tenson, Tanel; Myers, Andrew G; Hauryliuk, Vasili (17 June 2022). "Synthetic oxepanoprolinamide iboxamycin is active against Listeria monocytogenes despite the intrinsic resistance mediated by VgaL/Lmo0919 ABCF ATPase". JAC-Antimicrobial Resistance. 4 (3) dlac061. doi:10.1093/jacamr/dlac061. ISSN 2632-1823. PMC 9204466. PMID 35733912.
  3. ^ Wu, Kelvin J.Y.; Klepacki, Dorota; Mankin, Alexander S.; Myers, Andrew G. (July 2023). "A method for tritiation of iboxamycin permits measurement of its ribosomal binding". Bioorganic & Medicinal Chemistry Letters. 91 129364. doi:10.1016/j.bmcl.2023.129364. PMC 10408240. PMID 37295615.


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