Chemistry:Isepamicin

From HandWiki

Isepamicin (isepamycin) is an aminoglycoside antibiotic.

It was patented in 1973 and approved for medical use in 1988.[1] It has been identified by the World Health Organization as a Critically Important Antimicrobial for human use.[2]

Synthesis

Isepamicin can be synthesized by derivatization of gentamicin B (1) with benzyl N-[(2S)-3-(2,5-dioxopyrrolidin-1-yl)-2-hydroxy-3-oxopropyl]carbamate (2), followed by deprotection.[3][4][5][6]

Synthesis of isepamicin from gentamicin B

References

  1. (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 508. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA508. 
  2. "Critically important antimicrobials for human medicine.". World Health Organization. 2012. http://apps.who.int/iris/bitstream/10665/77376/1/9789241504485_eng.pdf. 
  3. Serradell, MN; Blancafort, P.; Roberts, PJ; Castaer, J.; SCH-21420. Drugs Fut 1979, 4, 7, 525.
  4. John J. Wright, U.S. Patent 4,029,882 (1977 to Merck Sharp and Dohme Corp).
  5. Thieme
  6. ChemDrug