Tilmicosin phosphate |
![]() Last updated: 15/09/2025 |
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(Not known by any other names) |
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A semi-synthetic macrolide antibiotic | |
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Used for the treatment and prevention of pneumonia associated with Pasteurella haemolytica, P. multocida, Actinobacillus pleuropneumoniae, mycoplasma species and other microorganisms | |
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Cattle; Sheep; Pigs; Poultry; Rabbits; Fish |
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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Tilmicosin phosphate exhibits geometric and stereoisomerism, primarily due to its macrolide structure and the presence of a piperidinyl side chain. The molecule contains both cis- and trans-isomers, which arise from the orientation of substituents around the double bonds and flexible ring systems within the macrolide core. Tilmicosin typically contains 82–88% cis-isomers and 12–18% trans-isomers, with the cis-isomer being the biologically active form. The phosphate salt form does not introduce additional isomerism. | |
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C₄₆H₈₃N₂O₁₇P | |
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CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(C(C(O2)C)O)N(C)C)O)CCN3CC(CC(C3)C)C)C)C)COC4C(C(C(C(O4)C)O)OC)OC.OP(=O)(O)O | |
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CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O)N(C)C)O)CCN3C[C@@H](C[C@@H](C3)C)C)C)\C)CO[C@H]4[C@@H]([C@@H]([C@@H]([C@H](O4)C)O)OC)OC.OP(=O)(O)O | |
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NESIVXZOSKKUDP-ARVJLQODSA-N | |
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InChI=1S/C46H80N2O13.H3O4P/c1-13-36-33(24-57-46-44(56-12)43(55-11)40(53)31(8)59-46)19-25(2)14-15-34(49)28(5)20-32(16-17-48-22-26(3)18-27(4)23-48)42(29(6)35(50)21-37(51)60-36)61-45-41(54)38(47(9)10)39(52)30(7)58-45;1-5(2,3)4/h14-15,19,26-33,35-36,38-46,50,52-54H,13,16-18,20-24H2,1-12H3;(H3,1,2,3,4)/b15-14+,25-19+;/t26-,27+,28-,29+,30-,31-,32+,33-,35-,36-,38+,39-,40-,41-,42-,43-,44-,45+,46-;/m1./s1 | |
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Yes |
General status |
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Antibiotic, Antibacterial, Antimicrobial, Medicinal drug, Medicated feed additive | |
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Macrolide | |
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Semi-synthetic | |
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Interferes with protein synthesis | |
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[50S rRNA, Antagonist] | |
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137330-13-3 | |
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641-061-9 | |
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5282522 | |
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Antiinfectants for systemic use: Antibacterials for systemic use | |
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QJ01FA91 | |
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No | |
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Allowed substance (Table 1: All food producing species) | |
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967.1 | |
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(4R,5S,6S,7R,9R,11E,13E,15R,16R)-6-[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3R,5S)-3,5-dimethylpiperidin-1-yl]ethyl]-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione;phosphoric acid | |
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Commercial |
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Current | |||
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1996, first registrations | |||
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A wide variety of formulations are available including solutions for injection, granules and premixed medicated feeds | |||
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The production of tilmicosin phosphate begins with the fermentation of Streptomyces fradiae to obtain tylosin, a macrolide antibiotic that serves as the starting material. The tylosin broth is first pretreated and filtered to isolate the active compound, which then undergoes a chemical modification involving ammoniation and hydrolysis to remove specific functional groups and generate tilmicosin, a semi-synthetic derivative. This intermediate is then subjected to a phosphorylation reaction, typically by reacting tilmicosin with phosphoric acid in an organic solvent such as acetone or chloroform under controlled temperature and pH conditions. The resulting tilmicosin phosphate is crystallised, washed and dried. | |||
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As microbial-based products tend to use fermentation-based production processes rather than chemical synthesis, they typically have a lower fossil fuel input in formulation and active ingredient creation, and also have reduced downstream emissions due to biodegradability and minimal soil disruption, their life-cycle GHG emissions are expected to be low. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg. |
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3.80 X 1002 | Calculated | - | |||||||
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2.58 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source |
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May be introduced into the environment via the spreading of waste products from treated animals |
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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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Fate indices |
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450 | V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Estimated1 = Estimated data with little or no verification |
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Not available | - |
Known soil and groundwater metabolites |
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Other known metabolites |
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tilmicosin sulphate | - | Rat | - | ||||
N-desmethyl tilmicosin | - | Animal | - |
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Terrestrial ecotoxicology |
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> 800 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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> 4710 mg kg feed⁻¹ | E4 E = Manufacturers safety data sheets Anas platyrhynchos4 = Verified data |
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> 918 | E3 E = Manufacturers safety data sheets Eisenia foetida 28 day3 = Unverified data of known source |
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Aquatic ecotoxicology |
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851 | E4 E = Manufacturers safety data sheets Oncorhynchus mykiss4 = Verified data |
Low | ||||||||
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57.3 | E4 E = Manufacturers safety data sheets Daphnia magna4 = Verified data |
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0.35 | E4 E = Manufacturers safety data sheets Raphidocelis subcapitata4 = Verified data |
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General |
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High (class III) | - | - | ||||||||
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> 800 | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) Rat5 = Verified data used for regulatory purposes |
Moderate | ||||||||
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Very little metabolism, excreted unchanged predominately in the faeces | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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Health issues |
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Severe allergen Cardiovascular toxicant |
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May emit toxic fumes when heated to decomposition | |||
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Not listed (Not listed) | |||
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tilmicosin phosphate | ||
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tilmicosine | ||
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tilmicosina | ||
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Record last updated: | 15/09/2025 |
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 |