Apramycin

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Apramycin
Apramycin.svg
Systematic (IUPAC) name
(2R,3R,4R,5S,6R)-5-amino-2- [((1R,2R,3R,4R,6R,8R)-8-amino-9- [(1R,2S,3R,4R,6R)-4,6-diamino-2,3- dihydroxy-cyclohexyl]oxy-2-hydroxy- 3-methylamino-5,10- dioxabicyclo[4.4.0]dec-4-yl)oxy]-6- (hydroxymethyl)oxane-3,4-diol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
?
Identifiers
CAS number 37321-09-8 N
ATCvet code QA07AA92 QJ01GB90 QJ51GB90
PubChem CID 3081545
DrugBank DB04626
ChemSpider 2339128 YesY
UNII 388K3TR36Z YesY
KEGG D02322 YesY
ChEBI CHEBI:2790 YesY
ChEMBL CHEMBL1230961 N
Chemical data
Formula C21H41N5O11 
Mol. mass 539.58 g/mol
 N (what is this?)  (verify)

Apramycin (also Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.[1]

Pharmacology[edit]

Indication[edit]

Apramycin is used for the treatment of bacterial infections in animals.

Mechanism of action[edit]

Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria.

Spectrum of bacterial susceptibility and resistance[edit]

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

[2]

References[edit]

  1. ^ Ryden, R; Moore (1977). "BJ". J Antimicrob Chemother 3 (6): 609–613. doi:10.1093/jac/3.6.609. PMID 340441. 
  2. ^ http://antibiotics.toku-e.com/antimicrobial_1728.html