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Details

Stereochemistry RACEMIC
Molecular Formula C22H13Cl2I2N2O2.Na.2H2O
Molecular Weight 721.086
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOSANTEL SODIUM DIHYDRATE

SMILES

O.O.[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=LFXWZVWDMPUFBW-UHFFFAOYSA-M
InChI=1S/C22H14Cl2I2N2O2.Na.2H2O/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);;2*1H2/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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
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
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 use of moxidectin or closantel in combination with levamisole in the control of nematodes of sheep in the highlands of central Kenya.
2002 Nov
Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya.
2002 Sep
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 Apr 18
Evolution of high-level, multiple anthelmintic resistance on a sheep farm in Malaysia.
2003 Feb
Analysis of OSPAR priority pharmaceuticals using high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry.
2006 Nov 17
Closantel toxicosis in kid goats.
2006 Oct 21
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
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
Determination of closantel residues in milk and animal tissues by HPLC with fluorescence detection and SPE with oasis MAX cartridges.
2008 Apr
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
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 Jun
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
[Evaluation of the efficacy of antihelmintics compounds on parasitics gastrointestinal nematodes (Strongyloidea) of goats].
2008 Sep
Comparison of the time required to administer three different fluke and worm combination products to commercial beef cattle at housing.
2008 Spring
The potential to control Haemonchus contortus in indigenous South African goats with copper oxide wire particles.
2009 Jun 10
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.
2010 Aug 5
Multiple resistance to anthelmintics by Haemonchus contortus and Trichostrongylus colubriformis in sheep in Brazil.
2010 Dec
Screening of closantel and rafoxanide in animal muscles by HPLC with fluorescence detection and confirmation using MS.
2010 Feb
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010 Feb 3
Polioencephalomalacia associated with closantel overdosage in a goat.
2010 Jun
Assay strategies for the discovery and validation of therapeutics targeting Brugia pahangi Hsp90.
2010 Jun 15
Anthelmintic efficacy and management practices in sheep farms from the state of Rio de Janeiro, Brazil.
2010 Jun 24
A novel high throughput assay for anthelmintic drug screening and resistance diagnosis by real-time monitoring of parasite motility.
2010 Nov 16
Nasal bots...a fascinating world!
2010 Nov 24
Multiple resistance of gastrointestinal nematodes to nine different drugs in a sheep flock in southern Brazil.
2010 Oct 11
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:48:19 GMT 2023
Edited
by admin
on Fri Dec 15 18:48:19 GMT 2023
Record UNII
181924B87F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOSANTEL SODIUM DIHYDRATE
EP  
Official Name English
CLOSANTEL SODIUM DIHYDRATE FOR VETERINARY USE [EP MONOGRAPH]
Common Name English
CLOSANTEL SODIUM DIHYDRATE FOR VETERINARY USE [EP IMPURITY]
Common Name English
5'-CHLORO-4'-(4-CHLORO-.ALPHA.-CYANOBENZYL)-3,5-DI-IODOSALICYL-O-TOLUIDIDE SODIUM DIHYDRATE
Common Name English
Code System Code Type Description
SMS_ID
300000029132
Created by admin on Fri Dec 15 18:48:19 GMT 2023 , Edited by admin on Fri Dec 15 18:48:19 GMT 2023
PRIMARY
FDA UNII
181924B87F
Created by admin on Fri Dec 15 18:48:19 GMT 2023 , Edited by admin on Fri Dec 15 18:48:19 GMT 2023
PRIMARY
PUBCHEM
91886168
Created by admin on Fri Dec 15 18:48:19 GMT 2023 , Edited by admin on Fri Dec 15 18:48:19 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY