U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H11Cl2I2NO3
Molecular Weight 626.01
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAFOXANIDE

SMILES

OC1=C(C=C(I)C=C1I)C(=O)NC2=CC=C(OC3=CC=C(Cl)C=C3)C(Cl)=C2

InChI

InChIKey=NEMNPWINWMHUMR-UHFFFAOYSA-N
InChI=1S/C19H11Cl2I2NO3/c20-10-1-4-13(5-2-10)27-17-6-3-12(9-15(17)21)24-19(26)14-7-11(22)8-16(23)18(14)25/h1-9,25H,(H,24,26)

HIDE SMILES / InChI
Rafoxanide is a halogenated salicylanilide used as a fasciolicide in cattle, sheep, goats, and horses. It is also active against nematodes, and the sheep nasal bot fly. Rafoxanide acts as by uncoupling oxidative phosphorylation of flukes, including reduced ATP levels, decreased glycogen content and accumulation of succinate.

Originator

Curator's Comment: Department of Chemical Pathology, King's College Hospital Medical School; Denmark Hill, London, England

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Fenafluke

Approved Use

Rafoxanide is used as a fasciolicide in cattle, sheep, goats, and horses.
PubMed

PubMed

TitleDatePubMed
Anthelmintic resistance on an organized sheep farm in India.
2001 Jul
Field trial on comparative efficacy of four fasciolicides against natural liver fluke infection in cattle.
2006 Feb 18
A dual anthelmintic treatment strategic scheme for the control of fasciolosis in dairy sheep farms.
2006 Nov
Comparative efficacy of different anthelmintics against fenbendazole-resistant nematodes of pashmina goats.
2007 Aug
Haemonchus contortus acetylcholine receptors of the DEG-3 subfamily and their role in sensitivity to monepantel.
2009 Apr
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.
2009 Jul 14
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
Biochemical analysis of a recombinant glutathione transferase from the cestode Echinococcus granulosus.
2010 Apr
Interaction of anthelmintic drugs with P-glycoprotein in recombinant LLC-PK1-mdr1a cells.
2010 Aug 5
Effect of three anthelmentics on disposition kinetics of florfenicol in goats.
2010 Dec
Screening of closantel and rafoxanide in animal muscles by HPLC with fluorescence detection and confirmation using MS.
2010 Feb
Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection.
2010 Sep-Oct
An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide.
2012 Jan 5
Patents

Sample Use Guides

The recommended dose range from 5 to 15 mg/kg bw is generally administered by oral gavage or by intra-ruminal route.
Route of Administration: Oral
In Vitro Use Guide
Flukes recovered from infected sheep were maintained in laboratory conditions in warm (37 deg-C) Hedon-Fleig saline and used within one hour of recovery. Rafoxanide tested in a concentration range of 0.01 to 1000 micro-g/mL as the commercial solutions, and in ethanol, dimethyl sulphoxide and Tween 80. Rafoxanide demonstrated faciolicide activity and a dose-response relationship. The motility of Fasciola hepatica was monitored by means of an isometric transducer connected to a high-speed pen recorder
Name Type Language
RAFOXANIDE
INN   MART.   MI   USAN  
USAN   INN  
Official Name English
N-(3-CHLORO-4-(4-CHLOROPHENOXY)PHENYL)-2-HYDROXY-3,5-DIIODOBENZAMIDE
Systematic Name English
RAFOXANIDE [MART.]
Common Name English
3'-CHLORO-4'-(4-CHLOROPHENOXY)-3,5-DIIODOSALICYLANILIDE
Systematic Name English
rafoxanide [INN]
Common Name English
BENZAMIDE, N-(3-CHLORO-4-(4-CHLOROPHENOXY)PHENYL)-2-HYDROXY-3,5-DIIODO-
Systematic Name English
NSC-355278
Code English
3'-CHLORO-4'-(P-CHLOROPHENOXY)-3,5-DIIODOSALICYLANILIDE
Common Name English
RAFOXANIDE [MI]
Common Name English
RAFOXANIDE [USAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QP52AG05
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL287542
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PRIMARY
ECHA (EC/EINECS)
245-148-9
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EVMPD
SUB10241MIG
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NSC
355278
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
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EPA CompTox
DTXSID5046227
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INN
2938
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CAS
22662-39-1
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NCI_THESAURUS
C152146
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WIKIPEDIA
RAFOXANIDE
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MERCK INDEX
m9484
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PRIMARY Merck Index
PUBCHEM
31475
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ALANWOOD
rafoxanide
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
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MESH
D011888
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FDA UNII
22F4FLA7DH
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
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SMS_ID
100000080290
Created by admin on Fri Dec 15 15:23:58 GMT 2023 , Edited by admin on Fri Dec 15 15:23:58 GMT 2023
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