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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
Structure of CLOSANTEL SODIUM

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

HIDE SMILES / InChI

Description
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CLOSANTEL

Approved Use

for veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases
Curative
CLOSANTEL

Approved Use

for veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases
Curative
CLOSANTEL

Approved Use

for veterinary use on CATTLE, SHEEP and GOATS against flukes, roundworms and myiases
PubMed

PubMed

TitleDatePubMed
Reduced efficacy of ivermectin, abamectin and moxidectin against field isolates of Haemonchus contortus.
2001 Dec
Anthelmintic resistance on an organized sheep farm in India.
2001 Jul
Blindness in lambs due to inadvertent closantel overdose.
2002 Jul 6
Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya.
2002 Sep
Epidemiology of Oestrus ovis infection of sheep in Argentina's Western Pampas.
2004 Dec
Myelin vacuolation, optic neuropathy and retinal degeneration after closantel overdosage in sheep and in a goat.
2007 Feb-Apr
Purification, reconstitution, and characterization of the CpxRAP envelope stress system of Escherichia coli.
2007 Mar 23
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
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.
2010 Aug 5
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010 Feb 3
Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection.
2010 Sep-Oct
Design, synthesis, and biological activities of closantel analogues: structural promiscuity and its impact on Onchocerca volvulus.
2011 Jun 9
An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.
2012 Jan 5
Patents

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
In Vitro Use Guide
Unknown
Name Type Language
CLOSANTEL SODIUM
Common Name English
5'-CHLORO-4'-(4-CHLORO-.ALPHA.-CYANOBENZYL)-3,5-DI-IODOSALICYL-O-TOLUIDIDE
Common Name English
R-34828
Code English
BENZAMIDE, N-(5-CHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)-2-METHYLPHENYL)-2-HYDROXY-3,5-DIIODO-, MONOSODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
Code System Code Type Description
CAS
61438-64-0
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
PRIMARY
PUBCHEM
23683671
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
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FDA UNII
0ZBS9YC04P
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
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NCI_THESAURUS
C96558
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID00977001
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
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SMS_ID
300000029131
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
262-794-7
Created by admin on Fri Dec 15 19:14:33 GMT 2023 , Edited by admin on Fri Dec 15 19:14:33 GMT 2023
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