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)
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 |
---|---|---|
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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Validated method for determination of ultra-trace closantel residues in bovine tissues and milk by solid-phase extraction and liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2007 Dec 21 |
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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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[Evaluation of the efficacy of antihelmintics compounds on parasitics gastrointestinal nematodes (Strongyloidea) of goats]. | 2008 Sep |
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Comparison of the time required to administer three different fluke and worm combination products to commercial beef cattle at housing. | 2008 Spring |
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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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Anthelmintic efficacy and management practices in sheep farms from the state of Rio de Janeiro, Brazil. | 2010 Jun 24 |
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:
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QP52AG09
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closantel
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)