Compound ID | 1845

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Apramycin

Synonym(s): EBL-1003

Class: Aminoglycoside

Spectrum of activity: Gram-negative
Details of activity: Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-negative bacteria
Description: Streptomyces natural product. Veterinary use, redeveloped for human use
Institute where first reported: Juvabis (human use)
Year first mentioned: 1979
Highest development stage: Phase 1 for human use (as of 2022)
Development status: Approved for veterinary use, off-patent
Chemical structure(s):
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Molecular weight: 539.58
Iso. SMILES: CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O
InChI Key: XZNUGFQTQHRASN-XQENGBIVSA-N
Can. SMILES: CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@@H](O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)O2)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)N)O)O)O
InChI: InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3081545
Guide to Pharmacology: apramycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/6374024/
  • https://www.clinicalmicrobiologyandinfection.com/article/S1198-743X(22)00259-2/fulltext
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7885111/
  • https://febs.onlinelibrary.wiley.com/doi/full/10.1111/j.1432-1033.1979.tb13295.x?sid=nlm%3Apubmed

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