Closantel
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Basic Info
| Common Name | Closantel(F05781) |
| 2D Structure | |
| FRCD ID | F05781 |
| CAS Number | 57808-65-8 |
| PubChem CID | 42574 |
| Formula | C22H14Cl2I2N2O2 |
| IUPAC Name | N-[5-chloro-4-[(4-chlorophenyl)-cyanomethyl]-2-methylphenyl]-2-hydroxy-3,5-diiodobenzamide |
| InChI Key | JMPFSEBWVLAJKM-UHFFFAOYSA-N |
| InChI | InChI=1S/C22H14Cl2I2N2O2/c1-11-6-15(17(10-27)12-2-4-13(23)5-3-12)18(24)9-20(11)28-22(30)16-7-14(25)8-19(26)21(16)29/h2-9,17,29H,1H3,(H,28,30) |
| Canonical SMILES | CC1=CC(=C(C=C1NC(=O)C2=CC(=CC(=C2O)I)I)Cl)C(C#N)C3=CC=C(C=C3)Cl |
| Isomeric SMILES | CC1=CC(=C(C=C1NC(=O)C2=CC(=CC(=C2O)I)I)Cl)C(C#N)C3=CC=C(C=C3)Cl |
| Synonyms |
N-(5-chloro-4-((4-chlorophenyl)(cyano)methyl)-2-methylphenyl)-2-hydroxy-3,5-diiodobenzamide
Closantel
57808-65-8
Closantelum [INN-Latin]
C22H14Cl2I2N2O2
EINECS 260-967-1
NSC 335306
CHEMBL12131
MLS001332593
CHEBI:77054
|
| Classifies |
Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Diphenylacetonitriles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diphenylacetonitriles |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Diphenylacetonitrile - Benzanilide - Aromatic anilide - Diphenylmethane - Salicylamide - Salicylic acid or derivatives - 3-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Benzoic acid or derivatives - Benzamide - 2-halophenol - 4-halophenol - 2-iodophenol - Benzoyl - 4-iodophenol - Iodobenzene - Halobenzene - Chlorobenzene - Phenol - Toluene - Aryl halide - Aryl iodide - Aryl chloride - Vinylogous acid - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Nitrile - Carbonitrile - Organic nitrogen compound - Organohalogen compound - Organic oxide - Organochloride - Organoiodide - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organopnictogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 663.075 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Complexity | 652 |
| Monoisotopic Mass | 661.852 |
| Exact Mass | 661.852 |
| XLogP | 7.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 30 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cattle,Edible Offal | Japan | 1ppm | |||
| Sheep,Kidney | Japan | 5. oppm | |||
| Cattle,Kidney | Japan | 3.0ppm | |||
| Cattle,Liver | Japan | 1.0ppm | |||
| Sheep,Fat | Japan | 2. oppm | |||
| Cattle,Fat | Japan | 3.0ppm | |||
| Sheep,Muscle | Japan | 1.5ppm | |||
| Cattle,Muscle | Japan | 1.0ppm | |||
| Sheep,Liver | Japan | 1.5ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Liver fluke control on sheep farms in Northern Ireland: A survey of changingmanagement practices in relation to disease prevalence and perceivedtriclabendazole resistance. | Vet Parasitol | 2016 Jan 30 | 26801598 |
| Fasciola hepatica: Histological changes in the somatic and reproductive tissuesof liver fluke following closantel treatment of experimentally-infected sheep. | Vet Parasitol | 2016 Jan 15 | 26790736 |
| Effect In Vitro of Antiparasitic Drugs on Microbial Inhibitor Test Responses for Screening Antibiotic Residues in Goat's Milk. | J Food Prot | 2015 Sep | 26319732 |
| Fasciola hepatica: a comparative survey of adult fluke resistance totriclabendazole, nitroxynil and closantel on selected upland and lowland sheepfarms in Northern Ireland using faecal egg counting, coproantigen ELISA testingand fluke histology. | Vet Parasitol | 2015 Jan 15 | 25529143 |
| Comparative method validation for closantel determination in cattle and sheepmilk according to European Union Volume 8 and Veterinary International Conferenceon Harmonization guidelines. | J Chromatogr A | 2014 Aug 1 | 24656540 |
| Investigation of the persistence of closantel residues in bovine milk followinglactating-cow and dry-cow treatments and its migration into dairy products. | J Agric Food Chem | 2013 Sep 11 | 23992251 |
| [Determination of phenolic and salicylanilide anthelmintics in liquid milk byhigh performance liquid chromatography]. | Se Pu | 2013 Oct | 24432649 |
| Ivermectin residue depletion in food producing species and its presence in animalfoodstuffs with a view to human safety. | Curr Pharm Biotechnol | 2012 May | 22039793 |
| Integrating fasciolosis control in the dry cow management: the effect ofclosantel treatment on milk production. | PLoS One | 2012 | 22916226 |
| Stability during cooking of anthelmintic veterinary drug residues in beef. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011Feb | 21240825 |
| Determination of closantel and rafoxanide in animal tissues by online anionicmixed-mode solid-phase extraction followed by isotope dilution liquidchromatography tandem mass spectrometry. | J Sep Sci | 2011 Jun | 21560244 |
| The comparative efficacy of four anthelmintics against a natural acquiredFasciola hepatica infection in hill sheep flock in the west of Ireland. | Vet Parasitol | 2009 Oct 14 | 19556063 |
| Validated method for determination of ultra-trace closantel residues in bovinetissues and milk by solid-phase extraction and liquid chromatography-electrosprayionization-tandem mass spectrometry. | J Chromatogr A | 2007 Dec 21 | 18001755 |
| Prevalence of benzimidazole resistant nematodes in sheep flocks in Yucatan,Mexico. | Vet Parasitol | 2003 May 15 | 12732464 |
| Comparative anthelmintic activity of strategic sustained low-level administrationof albendazole in feed pellets compared to single doses of closantel andtetramisole against natural ovine parasitic gastroenteritis. | Trop Anim Health Prod | 1999 Aug | 10504099 |
| Comparative pharmacokinetic disposition of closantel in sheep and goats. | J Vet Pharmacol Ther | 1993 Sep | 8230396 |
| The role of multigeneration studies in safety assessment of residues of veterinary drugs and additives. | Ann Ist Super Sanita | 1992 | 1303033 |