Apramycin

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

Apramycin

Clinical data
Trade names	Apralan
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- dihydroxy-cyclohexyl]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.

References

1. "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
2. Ryden R, Moore BJ (November 1977). "The in vitro activity of apramycin, a new aminocyclitol antibiotic". The Journal of Antimicrobial Chemotherapy. 3 (6): 609–613. doi:10.1093/jac/3.6.609. PMID 340441.
3. "Apramycin". KnowledgeBase: The Antimicrobial Index.
4. Aguirre Rivera J, Larsson J, Volkov IL, Seefeldt AC, Sanyal S, Johansson M (March 2021). "Real-time measurements of aminoglycoside effects on protein synthesis in live cells". Proceedings of the National Academy of Sciences of the United States of America. 118 (9). Bibcode:2021PNAS..11813315A. doi:10.1073/pnas.2013315118. PMC 7936356. PMID 33619089.