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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
Structure of CLOSANTEL

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)

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
The effect of a parenteral ivermectin/closantel injection on the growth and reproductive development of early immature Fasciola hepatica in cattle.
2006 Nov 30
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
[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
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010 Feb 3
Anthelmintic efficacy and management practices in sheep farms from the state of Rio de Janeiro, Brazil.
2010 Jun 24
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
INN   MART.   MI   USAN  
USAN   INN  
Official Name English
closantel [INN]
Common Name English
N-(5-CHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)-2-METHYLPHENYL)-2-HYDROXY-3,5-DIIODOBENZAMIDE
Systematic Name English
CLOSANTEL [USAN]
Common Name English
R-31520
Code English
BENZAMIDE, N-(5-CHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)-2-METHYLPHENYL)-2-HYDROXY-3,5-DIIODO-
Systematic Name English
CLOSANTEL [MART.]
Common Name English
R 31,520
Code English
CLOSANTEL [MI]
Common Name English
(RS)-5'-CHLORO-4'-(4-CHLORO-.ALPHA.-CYANOBENZYL)-3,5-DIIODOSALICYL-O-TOLUIDIDE
Common Name English
NSC-335306
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
WHO-VATC QP52AG09
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
Code System Code Type Description
NSC
335306
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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CAS
57808-65-8
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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NCI_THESAURUS
C79920
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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FDA UNII
EUL532EI54
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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MERCK INDEX
m3666
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ChEMBL
CHEMBL12131
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PUBCHEM
42574
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EVMPD
SUB06769MIG
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ALANWOOD
closantel
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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MESH
C023342
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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EPA CompTox
DTXSID6040662
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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CAS
57808-65-8
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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INN
4049
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CHEBI
77053
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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ECHA (EC/EINECS)
260-967-1
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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SMS_ID
100000084012
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
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