Emodepside |
![]() Last updated: 06/09/2025 |
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(Also known as: BAY 44-4400; BAY 44-8; PF 1022-221) |
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A semi-synthetic, anthelmintic depsipeptide veterinary drug | |
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Effective against a number of gastrointestinal nematodes including ascarids and hookworms | |
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Cats; Dogs |
Approval status |
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Approved - legal class and its availability varies with product and application | |
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Approved |
Chemical structure |
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Emodepside exhibits complex stereoisomerism due to multiple chiral centres and its macrocyclic structure. Its isomerism arises from the specific configurations of amino acid and hydroxy acid residues, cis/trans amide bonds, and the overall ring conformation. These stereochemical features are critical for its biological activity, particularly its ability to bind to latrophilin receptors and exert anthelmintic effects. Only certain stereoisomers, especially those derived from the natural fungal metabolite PF1022A, are pharmacologically active, making stereoselective synthesis and purification essential in its production. | |
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C₆₀H₉₀N₆O₁₄ | |
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CC1C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)O1)CC(C)C)C)CC2=CC=C(C=C2)N3CCOCC3)CC(C)C)C)C)CC(C)C)C)CC4=CC=C(C=C4)N5CCOCC5)CC(C)C)C | |
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C[C@@H]1C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O1)CC(C)C)C)CC2=CC=C(C=C2)N3CCOCC3)CC(C)C)C)C)CC(C)C)C)CC4=CC=C(C=C4)N5CCOCC5)CC(C)C)C | |
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ZMQMTKVVAMWKNY-YSXLEBCMSA-N | |
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InChI=1S/C60H90N6O14/c1-37(2)31-47-57(71)77-41(9)53(67)61(11)50(34-40(7)8)60(74)80-52(36-44-17-21-46(22-18-44)66-25-29-76-30-26-66)56(70)64(14)48(32-38(3)4)58(72)78-42(10)54(68)62(12)49(33-39(5)6)59(73)79-51(55(69)63(47)13)35-43-15-19-45(20-16-43)65-23-27-75-28-24-65/h15-22,37-42,47-52H,23-36H2,1-14H3/t41-,42-,47+,48+,49+,50+,51-,52-/m1/s1 | |
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Yes |
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Common Name | Relationship | Link |
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emodepside hydrate | - | ![]() |
General status |
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Antiparasitic, Anthelmintic, Nematicide | |
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Cyclic octadepsipeptides | |
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>950g kg⁻¹ | |
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Semi-synthetic | |
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Acts by stimulation of the presynaptic latrophilin receptor causing paralysis and death of the parasite | |
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[Latrophilin receptor, Binder] | |
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155030-63-0 | |
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Antiparasitic products, insecticides & repellents: Anthelmintics | |
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QP52AA51 | |
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No | |
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1119.39 | |
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cyclo[(R)-2-hydroxypropanoyl-(N-méthyl-L-leucyl)-[(R)-3-[4-(morpholin-4-yl)phényl]-2-hydroxypropanoyl]-(N-méthyl-L-leucyl)-(R)-2-hydroxypropanoyl-(N-méthyl-L-leucyl)-[(R)-3-[4-(morpholin-4-yl)phényl]-2-hydroxypropanoyl]-(N-méthyl-L-leucyl)] | |
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White to pale yellow powder | |
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Commercial |
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Current | |||
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1990, research started | |||
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Usually available as pour-on products or modified-release tablets for oral administration | |||
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Emodepside is synthesised through a multi-step process starting from its natural precursor, PF1022A, a cyclooctadepsipeptide produced by Mycelia sterilia. The first step involves chemical modification of PF1022A, typically by introducing a morpholine moiety at the para-position of the benzyl side chain to enhance pharmacological properties. This is achieved via selective alkylation or acylation reactions using reagents like p-morpholinobenzyl derivatives. The modified intermediate then undergoes macrocyclisation, often facilitated by coupling agents such as T3P/DIPEA or PyBOP/DIPEA, to form the final cyclic structure of emodepside. The product is purified through chromatographic techniques to isolate the correct stereoisomer, ensuring biological activity. This synthesis preserves the complex stereochemistry essential for its anthelmintic function. | |||
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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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5.2 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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4.9 | E3 E = Manufacturers safety data sheets 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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> 500 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
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Aquatic ecotoxicology |
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General |
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High (class III) | - | - | ||||||||
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> 500 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
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5000 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
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Faecal excretion predominates | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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No further information available |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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emodepside | ||
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Record last updated: | 06/09/2025 |
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 |