RAFOXANIDE

Possibly Marketed Outside US

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 Search

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

Molecular Formula	C19H11Cl2I2NO3
Molecular Weight	626.01
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015821.pdf |

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
malate dehydrogenase activity 1 Target ID: GO:0016615 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7264272	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fascioliasis 5 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015821.pdf https://www.drugs.com/international/rafoxanide.html	Primary		Approved 8429	Fenafluke Approved Use Rafoxanide is used as a fasciolicide in cattle, sheep, goats, and horses.

PubMed

Title	Date	PubMed
Comparative efficacy of different anthelmintics against fenbendazole-resistant nematodes of pashmina goats.	2007 Aug	17308986
Comparative pharmacokinetics of ivermectin alone and a novel formulation of ivermectin and rafoxanide in calves and sheep.	2008 May	18297309
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.	2009 Jul 14	19597541
The potential to control Haemonchus contortus in indigenous South African goats with copper oxide wire particles.	2009 Jun 10	19346076
Biochemical analysis of a recombinant glutathione transferase from the cestode Echinococcus granulosus.	2010 Apr	20034460
Effect of three anthelmentics on disposition kinetics of florfenicol in goats.	2010 Dec	20863870
Quantitative analysis of closantel and rafoxanide in bovine and ovine muscles by high-performance liquid chromatography with fluorescence detection.	2010 Sep-Oct	21140680

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:23:58 GMT 2023` Edited by `admin` on `Fri Dec 15 15:23:58 GMT 2023`
Record UNII	22F4FLA7DH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RAFOXANIDE

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