Apramycin

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

Apramycin

Clinical data
Trade names	Apralan
Other names	Nebramycin II
AHFS/Drugs.com	International Drug Names
ATCvet code	QA07AA92 (WHO) QJ01GB90 (WHO) QJ51GB90 (WHO)
Legal status
Legal status	CA: ℞-only[1]
Identifiers
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-dihydroxycyclohexyl]oxy-2-hydroxy-3-methylamino-5,10-dioxabicyclo[4.4.0]dec-4-yl)oxy]-6-(hydroxymethyl)oxane-3,4-diol
CAS Number	37321-09-8 N
PubChem CID	3081545
DrugBank	DB04626 Y
ChemSpider	2339128 Y
UNII	388K3TR36Z
KEGG	D02322 Y
ChEBI	CHEBI:2790 Y
ChEMBL	ChEMBL1230961 N
CompTox Dashboard (EPA)	DTXSID5045465
ECHA InfoCard	100.048.582
Chemical and physical data
Formula	C21H41N5O11
Molar mass	539.583 g·mol−1
3D model (JSmol)	Interactive image
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
NY (what is this?)  (verify)

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.