Apramycin

Chemical compound From Wikipedia, the free encyclopedia

Apramycin (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.[2]

Trade namesApralan
Other namesNebramycin II
AHFS/Drugs.comInternational Drug Names
ATCvet code
Quick facts Clinical data, Trade names ...
Apramycin
Clinical data
Trade namesApralan
Other namesNebramycin II
AHFS/Drugs.comInternational Drug Names
ATCvet code
Legal status
Legal status
Identifiers
  • (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-dihydroxycyclohexyl]oxy-2-hydroxy-3-methylamino-5,10-dioxabicyclo[4.4.0]dec-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4-diol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.582 Edit this at Wikidata
Chemical and physical data
FormulaC21H41N5O11
Molar mass539.583 g·mol−1
3D model (JSmol)
  • O3[C@H](O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O)[C@@H](NC)[C@@H](O)[C@H]4O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O)[C@H]2O)[C@H](N)C[C@H]34
  • 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 checkY
  • Key:XZNUGFQTQHRASN-XQENGBIVSA-N checkY
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Medical uses

Apramycin can be used to treat bacterial infections in animals caused by Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa.[citation needed] 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[3]

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.[4] This dual effect on both accuracy and efficiency of protein synthesis helps to explain the bactericidal properties of apramycin.

References

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