Apramycin |
Last updated: 20/03/2024 |
(Also known as: nebramycin II) |
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An antibiotic and antibacterial compound used in veterinary medicine | |
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Current | |
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1980s, first clinical use | |
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Typically used for the treatment of colibacillosis and salmonella in calves and bacterial enteritis in pigs and lambs | |
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Pigs; Lambs; Cattle; Chickens; Rabbits |
Approval status |
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Approved | |
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Approved |
Chemical structure |
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Isomeric | |
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C₂₁H₄₁N₅O₁₁ | |
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CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O | |
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CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O | |
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XZNUGFQTQHRASN-XQENGBIVSA-N | |
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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 | |
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Yes |
General status |
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Antibiotic, Antimicrobial, Antibacterial | |
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Aminoglycoside | |
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- | |
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- | |
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Synthetic | |
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Inhibitor of protein synthesis in bacteria both in vivo and in vitro | |
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[16S rRNA] | |
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37321-09-8 | |
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253-460-1 | |
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- | |
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- | |
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3081545 | |
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Antiinfectants for systemic use: Antibacterials for intramammary use; Alimentary tract & metabolism: Intestinal antiinfectants; Antiinfectants for systemic use: Antibacterials for systemic use | |
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QJ51GB90; QA07AA92; QJ01GB90 | |
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No | |
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Allowed substance (Table 1: Bovine, Ovine, Pocine, Chicken, Rabbit) | |
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539.58 | |
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- | |
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(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4αR,6S,7R,8αS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4α,6,7,8,8α-octahydropyrano[3,2-β]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol | |
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D-Streptamine,O-4-amino-4-deoxy-a-D-glucopyranosyl-(1®8)-O-(8R)-2-amino-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranosyl-(1®4)-2-deoxy- | |
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Colourless, needle-shaped crystals | |
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Formulations |
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Apravet Premix medicated feed | Huvepharma N.V. | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
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Often formulated as medicated feeds or as powders to be added to feed or drinking water |
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300000 | E3 E = Manufacturers safety data sheets 3 = Unverified data of known source |
High | ||||||||
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189 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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823 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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451.6 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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5.01 X 10-04 | Calculated | - | |||||||
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-3.3 | E3 E = Manufacturers safety data sheets 3 = Unverified data of known source |
Low | ||||||||
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1.56 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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8.5 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Main route into the environment from treated pigs is via animal urine and faeces. |
Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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- | E3 E = Manufacturers safety data sheets 3 = Unverified data of known source |
Non-mobile | |||||||
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500755 | ||||||||||
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Literature values Koc range 341900 - 659609 mL g⁻¹ | ||||||||||
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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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> 4160 | P3 P = Other non-EU, UK or US Governments and Regulators Rat as sulphate variant3 = Unverified data of known source |
Low | ||||||||
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1669 | E3 E = Manufacturers safety data sheets Colinus virginianus3 = Unverified data of known source |
Moderate | ||||||||
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> 100 | R4 R = Peer reviewed scientific publications Eisenia foetida4 = Verified data |
Low | ||||||||
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Aquatic ecotoxicology |
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300 | E3 E = Manufacturers safety data sheets Oncorhynchus mykiss3 = Unverified data of known source |
Low | ||||||||
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101.6 | E3 E = Manufacturers safety data sheets Daphnia magna3 = Unverified data of known source |
Low | ||||||||
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General |
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High (class III) | - | - | ||||||||
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> 4160 | P3 P = Other non-EU, UK or US Governments and Regulators Rat as sulphate variant3 = Unverified data of known source |
Low | ||||||||
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Intravenous LD₅₀ = 280 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
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Apramycin is rapidly absorbed when administered orally and is excreted via the kidneys without metabolisation | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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Possible kidney toxicant |
Handling issues |
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When heated to decomposition it emits acrid smoke and irritating fumes Corrosive |
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Health: H315 Environment: H410 |
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Not listed (Not listed) | |||
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apramycin | ||
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apramycine | ||
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apramicina | ||
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Record last updated: | 20/03/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |