Apramycin
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 457812269
| 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
| image = Apramycin.svg
| alt =
| tradename = Apralan
| Drugs.com = {{drugs.com|international|apramycin}}
| pregnancy_AU =
| pregnancy_category =
| routes_of_administration =
| legal_AU =
| legal_CA = Rx-only
| legal_CA_comment = {{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=Health Canada | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}
| legal_UK =
| legal_US =
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| synonyms = Nebramycin II
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 37321-09-8
| CAS_supplemental =
| ATCvet = yes
| ATC_prefix = A07
| ATC_suffix = AA92
| ATC_supplemental = {{ATCvet|J01|GB90}} {{ATCvet|J51|GB90}}
| PubChem = 3081545
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04626
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2339128
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 388K3TR36Z
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02322
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2790
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1230961
| C=21 | H=41 | N=5 | O=11
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XZNUGFQTQHRASN-XQENGBIVSA-N
}}
Apramycin (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.{{cite journal | vauthors = Ryden R, Moore BJ | title = The in vitro activity of apramycin, a new aminocyclitol antibiotic | journal = The Journal of Antimicrobial Chemotherapy | volume = 3 | issue = 6 | pages = 609–613 | date = November 1977 | pmid = 340441 | doi = 10.1093/jac/3.6.609 }}
Medical uses
Apramycin can be used to treat bacterial infections in animals caused by Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa.{{cn|date=March 2023}} 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{{cite web | title = Apramycin | url = http://antibiotics.toku-e.com/antimicrobial_1728.html | work = KnowledgeBase: The Antimicrobial Index }}
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.{{cite journal | vauthors = Aguirre Rivera J, Larsson J, Volkov IL, Seefeldt AC, Sanyal S, Johansson M | title = Real-time measurements of aminoglycoside effects on protein synthesis in live cells | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 118 | issue = 9 | date = March 2021 | pmid = 33619089 | pmc = 7936356 | doi = 10.1073/pnas.2013315118 | bibcode = 2021PNAS..11813315A | doi-access = free }} This dual effect on both accuracy and efficiency of protein synthesis helps to explain the bactericidal properties of apramycin.