Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H13Cl2I2N2O2.Na |
Molecular Weight | 685.056 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC1=CC(C(C#N)C2=CC=C(Cl)C=C2)=C(Cl)C=C1NC(=O)C3=C([O-])C(I)=CC(I)=C3
InChI
InChIKey=LREGMDNUOGTSIK-UHFFFAOYSA-M
InChI=1S/C22H14Cl2I2N2O2.Na/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);/q;+1/p-1
DescriptionCurator's Comment: description was created based on several sources, including
http://parasitipedia.net/index.php?option=com_content&view=article&id=2505&Itemid=2778
Curator's Comment: description was created based on several sources, including
http://parasitipedia.net/index.php?option=com_content&view=article&id=2505&Itemid=2778
Closantel is a synthetic anti parasitic agent which is highly effective against adults and larvae (6 to weeks old) of liver flukes (Fasciola hepatica), and against several important gastrointestinal roundworms (e.g. Bunostomum, Haemonchus, Oesophagostomum, Ostertagia - Teladorsagia, Strongyloides, Trichostrongylus), as well as against screwworms (maggots of Cochliomyia spp and Chrysomya spp), sheep nasal bots (Oestrus ovis), and sheep keds (Melophagus ovinus). The molecular mode of action closantel is not completely elucidated, but closantel decouples the mitochondrial oxidative phosphorylation, which leads to the inhibition of ATP synthesis, this seems to occur through suppression of the activity of succinate dehydrogenase and fumarate reductase, two enzymes involved in this process. Finally this all cause the death of the parasite. Recently it has been discovered that closantel also inhibits chitinase in Onchocerca volvulus, a filarial nematode causing river blindness in humans. Chitinase is an enzyme involved in larval molting. Its inhibition interrupts their development to adult worms. This drug possesses some side effects: hyper acute anaphylactic reactions in cattle; hypersensitivity reactions; overdoses can cause reduced visibility or blindness, anorexia, lack of coordination and general weakness.
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | CLOSANTEL Approved Usefor veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases |
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Curative | CLOSANTEL Approved Usefor veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases |
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Curative | CLOSANTEL Approved Usefor veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases |
PubMed
Title | Date | PubMed |
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Reduced efficacy of ivermectin, abamectin and moxidectin against field isolates of Haemonchus contortus. | 2001 Dec |
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Anthelmintic resistance on an organized sheep farm in India. | 2001 Jul |
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Blindness in lambs due to inadvertent closantel overdose. | 2002 Jul 6 |
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Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya. | 2002 Sep |
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Epidemiology of Oestrus ovis infection of sheep in Argentina's Western Pampas. | 2004 Dec |
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Myelin vacuolation, optic neuropathy and retinal degeneration after closantel overdosage in sheep and in a goat. | 2007 Feb-Apr |
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Purification, reconstitution, and characterization of the CpxRAP envelope stress system of Escherichia coli. | 2007 Mar 23 |
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Efficacy of 3 anthelmintics in communally grazed sheep as reflected by faecal egg count reduction tests in a semi-arid area of South Africa. | 2008 Mar |
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Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry. | 2009 Nov 13 |
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Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells. | 2010 Aug 5 |
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Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes. | 2010 Feb 3 |
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Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection. | 2010 Sep-Oct |
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Design, synthesis, and biological activities of closantel analogues: structural promiscuity and its impact on Onchocerca volvulus. | 2011 Jun 9 |
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An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide. | 2012 Jan 5 |
Patents
Sample Use Guides
in animals:
CATTLE
Oral Gastrointestinal roundworms: 5-10 mg/kg;
Oral Hypoderma spp: 10 mg/kg;
Subcutaneous Gastrointestinal roundworms: 3 mg/kg;
Subcutaneous Fasciola hepatica: 5 mg/kg;
SHEEP:
Oral Gastrointestinal roundworms: 5-10 mg/kg;
Oral Oestrus ovis: 5 mg/kg;
Oral Fasciola hepatica: 10 mg/kg;
Subcutaneous Gastrointestinal roundworms: 5-10 mg/kg;
GOATS:
Oral Gastrointestinal roundworms: 10 mg/kg;
Subcutaneous Gastrointestinal roundworms: 5 mg/kg
Route of Administration:
Other
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C250
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ACTIVE MOIETY
SUBSTANCE RECORD