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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

Molecular Formula C22H14Cl2I2N2O2
Molecular Weight 663.074
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Anthelmintic resistance on an organized sheep farm in India.
2001 Jul
Strategic control of gastrointestinal nematodes of sheep in the highlands of central Kenya.
2002 Sep
Field trial on the efficacy of an experimental fasciolicide compared with some commercial compounds in naturally infected cattle.
2003 Sep
Anthelmintic activity of Azadirachta indica A. Juss against sheep gastrointestinal nematodes.
2006 Apr 30
Intra-leukocyte expression of two-component systems in Ehrlichia chaffeensis and Anaplasma phagocytophilum and effects of the histidine kinase inhibitor closantel.
2006 Aug
Pharmacokinetics of a novel closantel/ivermectin injection in cattle.
2006 Jun
Analysis of OSPAR priority pharmaceuticals using high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry.
2006 Nov 17
The effect of a parenteral ivermectin/closantel injection on the growth and reproductive development of early immature Fasciola hepatica in cattle.
2006 Nov 30
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
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
The comparative efficacy of four anthelmintics against a natural acquired Fasciola hepatica infection in hill sheep flock in the west of Ireland.
2009 Oct 14
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
Assay strategies for the discovery and validation of therapeutics targeting Brugia pahangi Hsp90.
2010 Jun 15
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 16:12:40 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:40 GMT 2023
Record UNII
EUL532EI54
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
MERCK INDEX
m3666
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL12131
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
PRIMARY
PUBCHEM
42574
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
PRIMARY
EVMPD
SUB06769MIG
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
INN
4049
Created by admin on Fri Dec 15 16:12:40 GMT 2023 , Edited by admin on Fri Dec 15 16:12:40 GMT 2023
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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