Compound ID | 1844

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Tobramycin

Synonym(s): Nabramycin factor 6  |  nebramycin VI

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-positive and Gram-negative bacteria, especially Pseudomonas aeruginosa
Description: Streptomyces natural product. Veterinary use, human use primarily in combination therapy in Pseudomonas infections as inhaled therapy in Cystic Fibrosis patients
Institute where first reported: Lilly
Year first mentioned: 1965
Highest developmental phase: Approved by FDA in 1975
Development status: Approved, off-patent
Chemical structure(s):
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Molecular weight: 467.52
Iso. SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@H](O3)CN)O)N)N
InChI Key: NLVFBUXFDBBNBW-PBSUHMDJSA-N
Can. SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)N)O)O)O[C@@H]3[C@@H](C[C@@H]([C@@H](CN)O3)O)N)N
InChI: InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/36294
Guide to Pharmacology: tobramycin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/34998112/
  • https://pubmed.ncbi.nlm.nih.gov/35249787/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3038130/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC429354/

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