Structure via PubChem · Public domain (PubChem)
apramycin
Sign in to saveAlso known as nebramycin factor 2, nebramycin II, 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine, 4-O-(3alpha-amino-6alpha-((4-amino-4-deoxy-alpha-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-D-streptamine, Nebramycin II
Apramycin (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.
Chemical data
- Formula
- C21H41N5O11
- Molecular weight
- 539.6 g/mol
- IUPAC name
- (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol
- 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
- InChIKey
- XZNUGFQTQHRASN-XQENGBIVSA-N
- XLogP
- -7
- Polar surface area
- 284 Ų
- H-bond donors
- 11
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
492 papers- Apramycin has high in vitro activity against Mycobacterium tuberculosis.Journal of medical microbiology · 2024
- Apramycin resistance in epidemic carbapenem-resistant Klebsiella pneumoniae ST258 strains.The Journal of antimicrobial chemotherapy · 2021
- Apramycin Overcomes the Inherent Lack of Antimicrobial Bactericidal Activity in Mycobacterium abscessus.Antimicrobial agents and chemotherapy · 2022
- In vitro activity of apramycin against 16S-RMTase-producing Gram-negative isolates.Journal of global antimicrobial resistance · 2023
- Pharmacodynamic assessment of apramycin against Mycobacterium abscessus in a hollow fibre infection model.The Journal of antimicrobial chemotherapy · 2025
via PubMed
Wikidata facts
- Mass
- 539.28
Show 6 more facts
- chemical formula
- C₂₁H₄₁N₅O₁₁
- World Health Organisation international non-proprietary name
- apramycin
- isomeric 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
- canonical SMILES
- CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O
- subject has role
- bactericide
- found in taxon
- Streptomyces
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Medical uses
- Mechanism of action
- References
Apramycin (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.
== Medical uses == Apramycin can be used to treat bacterial infections in animals caused by Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa. The following shows susceptibility data on medically significant organisms: Escherichia coli - 1 μg/mL - >512 μg/mL (this large range may be due to resistant organisms, typical MIC values are likely in the range of 2 -8 μg/mL. Klebsiella pneumoniae - 2 μg/mL - >256 μg/mL Pseudomonas aeruginosa - 4 μg/mL == Mechanism of action == Traditional knowledge suggests that aminoglycosides bind to the bacterial ribosome, leading to misreading of mRNA and incorporation of incorrect amino acids in the nascent polypeptide chain. However, aminoglycosides, including apramycin, have been shown to not only cause misreading of the genetic code but also significantly slow down the overall rate of protein synthesis in live bacterial cells. This dual effect on both accuracy and efficiency of protein synthesis helps to explain the bactericidal properties of apramycin.
Excerpted from Wikipedia’s “apramycin” article, available under the CC BY-SA 4.0 licence.