Apramycin CAS 37321-09-8

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Model: MOS37321-09-8
CAS: 37321-09-8
Molecular formula: C21H41N5O11
Molecular weight: 539.5771
Refractive index: 1.657
Boiling point: 823°C at 760 mmHg
Flash point: 451.6°C
Density: 1.56g/cm3
Vapour Pressur: 2.11E-31mmHg at 25°C
Category:

Apramycin (CAS: 37321-09-8)

Synonyms (2R,3R,4S,5S,6S)-5-amino-2-{[(2R,3S,4R,4aR,7R,8aS)-7-amino-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy}-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (non-preferred name); 5-amino-2-({7-amino-6-[(4,6-diamino-2,3-dihydroxycyclohexyl)oxy]-4-hydroxy-3-(methylamino)octahydropyrano[3,2-b]pyran-2-yl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (non-preferred name); Aprymycin; 3,7-trideoxy-7-(methylamino)-d-glycero-alpha-d-allo-octadialdo-1,5:8,4-dipyra
Molecular Formula C21H41N5O11
Molecular Weight 539.5771
Density 1.56g/cm3
Boiling point 823°C at 760 mmHg
Refractive index 1.657
Flash point 451.6°C
Vapour Pressur 2.11E-31mmHg at 25°C
EINECS 253-460-1

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

Indication

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

Mechanism of action

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

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

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