Milbemycin oxime (Ref: CGA-179246) |
![]() Last updated: 09/09/2025 |
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(Also known as: Milbemycin-A4-oxim ) |
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A broad-spectrum antiparasitic drug producted by the fermentation by Streptomyces hygroscopicus variant aureolacrimosus | |
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Used for the treatment of heartworms, mites, fleas, ticks and nematodes (roundworms, tapeworms, hookworms) | |
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Dogs; Cats |
Approval status |
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Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Milbemycin oxime exhibits isomerism primarily through its oxime functional group and multiple chiral centres. The oxime moiety can exist in E/Z geometrical forms, depending on the spatial arrangement around the C=N bond. Additionally, the compound’s macrolide ring contains several stereocentres, giving rise to various stereoisomers, including enantiomers and diastereomers, which can influence its pharmacological properties. It’s commonly used as a mixture of A3 and A4 derivatives. | |
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C₆₃H₈₈N₂O₁₄ | |
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CCC1C(CCC2(O1)CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)C.CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)OC1C | |
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CC[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]\5[C@@]4([C@@H](C=C(/C5=N/O)C)C(=O)O3)O)C)\C)C.C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]\5[C@@]4([C@@H](C=C(/C5=N/O)C)C(=O)O3)O)C)\C)O[C@@H]1C | |
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CKVMAPHTVCTEMM-ALPQRHTBSA-N | |
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InChI=1S/C32H45NO7.C31H43NO7/c1-6-27-21(4)12-13-31(40-27)17-25-16-24(39-31)11-10-20(3)14-19(2)8-7-9-23-18-37-29-28(33-36)22(5)15-26(30(34)38-25)32(23,29)35;1-18-7-6-8-23-17-36-28-27(32-35)21(4)14-26(31(23,28)34)29(33)37-25-15-24(10-9-19(2)13-18)39-30(16-25)12-11-20(3)22(5)38-30/h7-10,15,19,21,24-27,29,35-36H,6,11-14,16-18H2,1-5H3;6-9,14,18,20,22,24-26,28,34-35H,10-13,15-17H2,1-5H3/b8-7+,20-10+,23-9+,33-28-;7-6+,19-9+,23-8+,32-27-/t19-,21-,24+,25-,26-,27+,29+,31+,32+;18-,20-,22+,24+,25-,26-,28+,30-,31+/m00/s1 | |
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Yes |
General status |
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Anthelmintic agent; Ectoparasiticide | |
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Micro-organism derived substance | |
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>95% | |
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Natural | |
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Opens glutamate sensitive chloride channels in neurons and myocytes of invertebrates, leading to hyperpolarisation of these cells and blocking of signal transfer. | |
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[GABA, Agonist] | |
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129496-10-2 | |
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Antiparasitic products, insecticides and repellents: Milbemycins | |
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QP54AB01 | |
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No | |
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1097.4 | |
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None | |
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mixture of 70% (10E,14E,16E)-(1R,4S,5'S,6R,6'R,8R,13R,20R,24S)-6'-ethyl-24-hydroxy-5',11,13,22-tetramethyl-(3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(tetrahydropyran)-2,21-dione 21-(EZ)-oxime and 30% (10E,14E,16E)-(1R,4S,5'S,6R,6'R,8R,13R,20R,24S)-24-hydroxy-5',6',11,13,22-pentamethyl-(3,7,19-trioxatetracyclo(15.6.1.14,8.020,24)pentacosa-10,14,16,22-tetraene)-6-spiro-2'-(tetrahydropyran)-2,21-dione 21-(EZ)-oxime | |
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(6R,25R)-5-demethoxy-28-deoxy-6,28-epoxy-25-ethyl-5-(hydroxyimino)milbemycin B mixture with (6R,25R)-5-demethoxy-28-deoxy-6,28-epoxy-5-(hydroxyimino)-25-methylmilbemycin B | |
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Crystalline solid |
Commercial |
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Current | |||
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Circa 1972, introduced | |||
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Usually formulated as tablets for oral administration | |||
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The production of milbemycin oxime involves a two-step chemical synthesis starting from milbemycin. First, an oxidation reaction is carried out using oxidising agents like hypochlorite or chlorite, with piperidine nitrogen-oxygen free radicals and halides acting as catalysts. This reaction, conducted in dichloromethane at low temperatures, converts milbemycin into an intermediate known as milbemycin ketone. Next, the ketone undergoes an oximation reaction, where it is treated with hydroxylamine hydrochloride in a 1,4-dioxane solvent, resulting in the formation of milbemycin oxime. | |||
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Milbemycin, itself, is a microbial-based compound produced via fermentation and will typically emit relatively low levels of GHGs during production. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg. However, the conversion to the oxime will increase emissions levels, potentially significantly. |
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Max @ 246nm | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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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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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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> 980 | P4 P = Other non-EU, UK or US Governments and Regulators Rat 4 = Verified data |
Moderate | ||||||||
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Aquatic ecotoxicology |
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0.059 | P4 P = Other non-EU, UK or US Governments and Regulators Cyprinus carpio4 = Verified data |
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> 100 | P4 P = Other non-EU, UK or US Governments and Regulators Daphnia magna4 = Verified data |
Low | ||||||||
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General |
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> 980 | P4 P = Other non-EU, UK or US Governments and Regulators Rat 4 = Verified data |
Moderate | ||||||||
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200 | P3 P = Other non-EU, UK or US Governments and Regulators Rat as product3 = Unverified data of known source |
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> 5.0 | P3 P = Other non-EU, UK or US Governments and Regulators Rat 4 hr3 = Unverified data of known source |
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Metabolised in the liver; biliary excretion | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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Harmful by inhalation and ingestion |
Handling issues |
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Non-corrosive Not expected to auto-ignite; Not highly flammable |
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Health: H302, H332 Environment: H400, H410 |
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Not listed (Not listed) | |||
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None allocated | |||
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milbemycin oxime | ||
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oxime de milbemycine | ||
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Record last updated: | 09/09/2025 |
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 |