CAS 119783-91-4

5-Deoxy-5-fluoroarbekacin

Description:

5-Deoxy-5-fluoroarbekacin is a synthetic aminoglycoside antibiotic that is structurally related to arbekacin, which is used primarily for its antibacterial properties. This compound exhibits a modified sugar moiety, where the hydroxyl group at the 5-position is replaced by a fluorine atom, enhancing its stability and potentially its efficacy against certain bacterial strains. The presence of the fluorine atom may also influence its pharmacokinetic properties, such as absorption and distribution within biological systems. 5-Deoxy-5-fluoroarbekacin is particularly noted for its activity against Gram-positive bacteria, including some strains resistant to other antibiotics. Its mechanism of action involves binding to the bacterial ribosome, inhibiting protein synthesis, which is crucial for bacterial growth and replication. As with other aminoglycosides, the use of this compound may be associated with potential nephrotoxicity and ototoxicity, necessitating careful monitoring during treatment. Overall, 5-Deoxy-5-fluoroarbekacin represents a significant advancement in the development of antibiotics aimed at combating resistant bacterial infections.

Formula: C₂₂H₄₃FN₆O₉

InChI: InChI=1/C22H43FN6O9/c23-14-18(37-21-9(26)2-1-8(6-25)35-21)10(27)5-11(29-20(34)12(31)3-4-24)19(14)38-22-17(33)15(28)16(32)13(7-30)36-22/h8-19,21-22,30-33H,1-7,24-28H2,(H,29,34)/t8-,9+,10-,11+,12-,13+,14-,15-,16+,17+,18+,19-,21+,22+/m0/s1

Synonyms:

• (S)-O-3-Amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-N1-(4-amino-2-hydroxy-1-oxobutyl)-2,5-dideoxy-5-fluoro-D-streptamine
• 5-Deoxy-5-epi-5-fluoro-arbekacin
• D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-N1-(4-amino-2-hydroxy-1-oxobutyl)-2,5-dideoxy-5-fluoro-, (S)-
• (2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl)oxy]-3-fluorocyclohexyl}-2-hydroxybutanamide