Apramycin
Chemical compound
- QA07AA92 (WHO) QJ01GB90 (WHO) QJ51GB90 (WHO)
- CA: ℞-only[1]
- (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
- 37321-09-8
N
- 3081545
- DB04626
Y
- 2339128 Y
- 388K3TR36Z
- D02322 Y
- CHEBI:2790 Y
- ChEMBL1230961 N
- DTXSID5045465
- Interactive image
- 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/s1Y
- Key:XZNUGFQTQHRASN-XQENGBIVSA-NY
N
Y (what is this?) (verify)Apramycin (also Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.[2]
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.[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
- ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
- ^ 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.
- ^ "Apramycin". KnowledgeBase: The Antimicrobial Index.
- ^ Aguirre Rivera, Javier; Larsson, Jimmy; Volkov, Ivan L.; Seefeldt, A. Carolin; Sanyal, Suparna; Johansson, Magnus (2021-03-02). "Real-time measurements of aminoglycoside effects on protein synthesis in live cells". Proceedings of the National Academy of Sciences. 118 (9). Bibcode:2021PNAS..11813315A. doi:10.1073/pnas.2013315118. ISSN 0027-8424. PMC 7936356. PMID 33619089.
- v
- t
- e
| Aminoglycosides (initiation inhibitors) |
| ||||||
|---|---|---|---|---|---|---|---|
| Tetracycline antibiotics (tRNA binding) |
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| Steroid antibacterials |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
