Diamfenetide |
![]() Last updated: 16/09/2025 |
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(Also known as: diamiphenethide; acemidophene) |
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An anthelminitic substance used to control trematode and other flatworm infestations | |
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Liver fluke (Fasciola hepatica); Flatworms | |
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Sheep; Cattle; Humans |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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Diamfenetide exhibits structural isomerism, particularly positional and conformational isomerism, due to its flexible ether-linked aromatic framework. The molecule contains two acetamide groups attached to para-substituted phenyl rings, which are connected via ethylenedioxy bridges. This arrangement allows for multiple conformers based on the rotation around the ether and amide bonds. | |
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C₂₀H₂₄N₂O₅ | |
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CC(=O)NC1=CC=C(C=C1)OCCOCCOC2=CC=C(C=C2)NC(=O)C | |
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JNEZCZPNQCQCFK-UHFFFAOYSA-N | |
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InChI=1S/C20H24N2O5/c1-15(23)21-17-3-7-19(8-4-17)26-13-11-25-12-14-27-20-9-5-18(6-10-20)22-16(2)24/h3-10H,11-14H2,1-2H3,(H,21,23)(H,22,24) | |
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Yes |
General status |
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Anthelmintic; Antiparasitic | |
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Benzamide derivative | |
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Synthetic | |
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Substance causing irreversible paralysis in flukes as well as affecting the fluke's metabolism, leading to an increase in glucose metabolism products and a decrease in ATP levels. | |
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[Metabolic interference and neuromuscular disruption] | |
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36141-82-9 | |
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252-886-5 | |
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37384 | |
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Anthelmintics | |
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None allocated | |
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No | |
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372.4 | |
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N,N′-{oxybis[(ethane-2,1-diyl)oxy-4,1-phenylene]}diacetamide | |
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4′,4‴-[oxybis(ethyleneoxy)]diacetanilide | |
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N,N′-[oxybis(2,1-ethanediyloxy-4,1-phenylene)]bis[acetamide] | |
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Off-white coloured, odourless solid |
Commercial |
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Obsolete | |||
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1970s, synthesised as a flukicide; 1980s, first vet use; 2013, not approved UK | |||
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Was typically formulated as an oral suspension or drench | |||
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The production of diamfenetide involves a condensation reaction between beta,beta′-dichloroethyl ether and acetaminophen (paracetamol). First, diethylene glycol is reacted with thionyl chloride in the presence of pyridine to produce the dichloroethyl ether intermediate. This reactive ether is then coupled with two equivalents of acetaminophen under controlled conditions, forming the final bis-acetamide structure of diamfenetide. The reaction typically proceeds in an organic solvent such as ethanol or acetone, followed by purification through crystallisation. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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140 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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661.8 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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354.1 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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3.22 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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1.595 | 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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Fate indices |
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Known metabolites |
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Terrestrial ecotoxicology |
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> 20000 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
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Aquatic ecotoxicology |
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General |
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> 20000 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
Low | ||||||||
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Intraperitoneal LD₅₀ > 6300 mg kg⁻¹ | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
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Eliminated via hepatic metabolism, followed by renal excretion of its active metabolite | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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No information available |
Handling issues |
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Will emit toxic gases if heated Incompatible with strong oxidising agents |
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Health: H315, H317, H319 Environment: H412 |
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Stable under ambient conditions |
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diamfenetide | ||
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diamfenetidium | ||
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diamfenetida | ||
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Record last updated: | 16/09/2025 |
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 |