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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=C(NC(=O)C2=C([O-])C(I)=CC(I)=C2)C=C(Cl)C(=C1)C(C#N)C3=CC=C(Cl)C=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

Molecular Formula C22H13Cl2I2N2O2
Molecular Weight 662.066
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.
2012-01-05
Design, synthesis, and biological activities of closantel analogues: structural promiscuity and its impact on Onchocerca volvulus.
2011-06-09
Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection.
2010-12-15
Multiple resistance to anthelmintics by Haemonchus contortus and Trichostrongylus colubriformis in sheep in Brazil.
2010-12
Nasal bots...a fascinating world!
2010-11-24
A novel high throughput assay for anthelmintic drug screening and resistance diagnosis by real-time monitoring of parasite motility.
2010-11-16
Multiple resistance of gastrointestinal nematodes to nine different drugs in a sheep flock in southern Brazil.
2010-10-11
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.
2010-08-05
Anthelmintic efficacy and management practices in sheep farms from the state of Rio de Janeiro, Brazil.
2010-06-24
Assay strategies for the discovery and validation of therapeutics targeting Brugia pahangi Hsp90.
2010-06-15
Polioencephalomalacia associated with closantel overdosage in a goat.
2010-06
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010-02-03
Screening of closantel and rafoxanide in animal muscles by HPLC with fluorescence detection and confirmation using MS.
2010-02
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
2009-11-13
The comparative efficacy of four anthelmintics against a natural acquired Fasciola hepatica infection in hill sheep flock in the west of Ireland.
2009-10-14
Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling.
2009-09-22
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.
2009-07-14
The potential to control Haemonchus contortus in indigenous South African goats with copper oxide wire particles.
2009-06-10
[Evaluation of the efficacy of antihelmintics compounds on parasitics gastrointestinal nematodes (Strongyloidea) of goats].
2008-09
The efficacy of an ivermectin/closantel injection against experimentally induced infections and field infections with gastrointestinal nematodes and liver fluke in cattle.
2008-08-17
A comparison of the efficacy of doramectin, closantel and levamisole in the treatment of the 'oriental eye fluke', Philophthalmus gralli, in commercially reared ostriches (Struthio camelus).
2008-06
Determination of closantel residues in milk and animal tissues by HPLC with fluorescence detection and SPE with oasis MAX cartridges.
2008-04
Efficacy of 3 anthelmintics in communally grazed sheep as reflected by faecal egg count reduction tests in a semi-arid area of South Africa.
2008-03
Comparison of the time required to administer three different fluke and worm combination products to commercial beef cattle at housing.
2008
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.
2007-12-21
Purification, reconstitution, and characterization of the CpxRAP envelope stress system of Escherichia coli.
2007-03-23
The effect of a parenteral ivermectin/closantel injection on the growth and reproductive development of early immature Fasciola hepatica in cattle.
2006-11-30
Analysis of OSPAR priority pharmaceuticals using high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry.
2006-11-17
Closantel toxicosis in kid goats.
2006-10-21
Intra-leukocyte expression of two-component systems in Ehrlichia chaffeensis and Anaplasma phagocytophilum and effects of the histidine kinase inhibitor closantel.
2006-08
Pharmacokinetics of a novel closantel/ivermectin injection in cattle.
2006-06
Anthelmintic activity of Azadirachta indica A. Juss against sheep gastrointestinal nematodes.
2006-04-30
Myelin vacuolation, optic neuropathy and retinal degeneration after closantel overdosage in sheep and in a goat.
2006-02-01
Rift Valley fever in small ruminants, Senegal, 2003.
2005-11
Epidemiology of Oestrus ovis infection of sheep in Argentina's Western Pampas.
2004-12
Field trial on the efficacy of an experimental fasciolicide compared with some commercial compounds in naturally infected cattle.
2003-09
The relationship between nasal myiasis and the prevalence of enzootic nasal tumours and the effects of treatment of Oestrus ovis and milk production in dairy ewes of Roquefort cheese area.
2003-04-18
Evolution of high-level, multiple anthelmintic resistance on a sheep farm in Malaysia.
2003-02
Strategic use of moxidectin or closantel in combination with levamisole in the control of nematodes of sheep in the highlands of central Kenya.
2002-11
Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya.
2002-09
Blindness in lambs due to inadvertent closantel overdose.
2002-07-06
Reduced efficacy of ivermectin, abamectin and moxidectin against field isolates of Haemonchus contortus.
2001-12
Anthelmintic resistance on an organized sheep farm in India.
2001-07
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:39:42 GMT 2025
Edited
by admin
on Mon Mar 31 19:39:42 GMT 2025
Record UNII
0ZBS9YC04P
Record Status Validated (UNII)
Record Version
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Name Type Language
CLOSANTEL SODIUM
Common Name English
R-34828
Preferred Name English
5'-CHLORO-4'-(4-CHLORO-.ALPHA.-CYANOBENZYL)-3,5-DI-IODOSALICYL-O-TOLUIDIDE
Common Name 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 Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
Code System Code Type Description
CAS
61438-64-0
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
PUBCHEM
23683671
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
FDA UNII
0ZBS9YC04P
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
NCI_THESAURUS
C96558
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID00977001
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
SMS_ID
300000029131
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
ECHA (EC/EINECS)
262-794-7
Created by admin on Mon Mar 31 19:39:42 GMT 2025 , Edited by admin on Mon Mar 31 19:39:42 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY