Apramycin

Apramycin

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
Identifiers
CAS Registry Number	37321-09-8 N
ATCvet code	QA07AA92 QJ01GB90 QJ51GB90
PubChem	CID 3081545
DrugBank	DB04626 Y
ChemSpider	2339128 Y
UNII	388K3TR36Z Y
KEGG	D02322 Y
ChEBI	CHEBI:2790 Y
ChEMBL	CHEMBL1230961 N
Chemical data
Formula	C21H41N5O11
Molecular mass	539.58 g/mol
SMILES 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 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  Y Key:XZNUGFQTQHRASN-XQENGBIVSA-N  Y
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

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

^[2]

References