Isepamicin
Chemical compound
- J01GB11 (WHO)
- (2S)-3-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-[(6-amino-6-deoxy-D-glucopyranosyl)oxy]-2-{[3-deoxy-4-C-methyl-3-(methylamino)-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl)-2-hydroxypropanamide
- 58152-03-7
Y
- 3037209
- 2301019
N
- G7K224460P
- ChEMBL272080
N
- DTXSID1048380
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- Interactive image
- C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O
InChI
- InChI=1S/C22H43N5O12/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-/m0/s1
N
- Key:UDIIBEDMEYAVNG-ZKFPOVNWSA-N
N
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Isepamicin (also 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
![](http://upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Isepamicin_synthesis.svg/500px-Isepamicin_synthesis.svg.png)
Gentamicin B [36889-15-3] (1) benzyl N-[(2S)-3-(2,5-dioxopyrrolidin-1-yl)-2-hydroxy-3-oxopropyl]carbamate, PC70561099 (2) (3)
References
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 508. ISBN 9783527607495.
- ^ "Critically important antimicrobials for human medicine" (PDF). World Health Organization. 2012.
- ^ Serradell, MN; Blancafort, P.; Roberts, PJ; Castaer, J.; SCH-21420. Drugs Fut 1979, 4, 7, 525.
- ^ John J. Wright, U.S. patent 4,029,882 (1977 to Merck Sharp and Dohme Corp).
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Aminoglycosides (initiation inhibitors) |
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Tetracycline antibiotics (tRNA binding) |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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