Compound ID | 262

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TS2037 (derivative of arbekicin)

Synonym(s): 5,4″-diepi-arbekacin

Class: Aminoglycoside

Agent Type: Synthetic; Small molecule;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Unknown
Target Pathogen: Active against methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa infections
Description: Synthetic compound derived from arbekacin; Maebashi K, Usui T, Hiraiwa Y, Akiyama Y, Otsuka K, et al. Synthesis and biological evaluation of TS2037, a novel aminoglycoside antibiotic. 44th-ICAAC 2004;202.
Institute where first reported: Meiji Seika Kaisha (Meiji Seika Pharma., Japan)
Year first mentioned: 2004
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Despite having the most potent antibacterial activity of the series, the nephrotoxicity needed improvement
Chemical structure(s):
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Molecular weight: 550.64
Iso. SMILES: O[C@@H]1[C@H](N)[C@@H](O)[C@@H](O[C@H]2[C@H](CC([C@@H](O)CCN)=O)C[C@H](C)[C@@H](O[C@@H]3[C@H](N)CC[C@@H](CN)O3)[C@H]2O)O[C@@H]1CO
InChI Key: KSMABBXQJLPPEX-HJISSGRMSA-N
Can. SMILES: C[C@H]1C[C@@H](CC(=O)[C@H](CCN)O)[C@@H]([C@@H]([C@@H]1O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)O)O[C@@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)N)O
InChI: InChI=1S/C24H46N4O10/c1-10-6-11(7-15(31)14(30)4-5-25)22(38-24-19(33)17(28)18(32)16(9-29)36-24)20(34)21(10)37-23-13(27)3-2-12(8-26)35-23/h10-14,16-24,29-30,32-34H,2-9,25-28H2,1H3/t10-,11-,12-,13+,14-,16+,17-,18-,19+,20+,21+,22-,23+,24+/m0/s1
External links:
Citations:
  • https://www.nature.com/articles/s41429-017-0002-2
  • https://www.nature.com/articles/s41429-017-0002-2

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