Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H14Cl2I2N2O2 |
Molecular Weight | 663.074 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=JMPFSEBWVLAJKM-UHFFFAOYSA-N
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)
Molecular Formula | C22H14Cl2I2N2O2 |
Molecular Weight | 663.074 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|
Anthelmintic resistance on an organized sheep farm in India. | 2001 Jul |
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Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya. | 2002 Sep |
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Field trial on the efficacy of an experimental fasciolicide compared with some commercial compounds in naturally infected cattle. | 2003 Sep |
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Anthelmintic activity of Azadirachta indica A. Juss against sheep gastrointestinal nematodes. | 2006 Apr 30 |
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Intra-leukocyte expression of two-component systems in Ehrlichia chaffeensis and Anaplasma phagocytophilum and effects of the histidine kinase inhibitor closantel. | 2006 Aug |
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Pharmacokinetics of a novel closantel/ivermectin injection in cattle. | 2006 Jun |
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Analysis of OSPAR priority pharmaceuticals using high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry. | 2006 Nov 17 |
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The effect of a parenteral ivermectin/closantel injection on the growth and reproductive development of early immature Fasciola hepatica in cattle. | 2006 Nov 30 |
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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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The efficacy of an ivermectin/closantel injection against experimentally induced infections and field infections with gastrointestinal nematodes and liver fluke in cattle. | 2008 Aug 17 |
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The comparative efficacy of four anthelmintics against a natural acquired Fasciola hepatica infection in hill sheep flock in the west of Ireland. | 2009 Oct 14 |
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Multiple resistance to anthelmintics by Haemonchus contortus and Trichostrongylus colubriformis in sheep in Brazil. | 2010 Dec |
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Screening of closantel and rafoxanide in animal muscles by HPLC with fluorescence detection and confirmation using MS. | 2010 Feb |
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Assay strategies for the discovery and validation of therapeutics targeting Brugia pahangi Hsp90. | 2010 Jun 15 |
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A novel high throughput assay for anthelmintic drug screening and resistance diagnosis by real-time monitoring of parasite motility. | 2010 Nov 16 |
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Nasal bots...a fascinating world! | 2010 Nov 24 |
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Multiple resistance of gastrointestinal nematodes to nine different drugs in a sheep flock in southern Brazil. | 2010 Oct 11 |
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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
Substance Class |
Chemical
Created
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admin
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Record UNII |
EUL532EI54
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Validated (UNII)
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