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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(I)C=C(I)C=C1C(=O)NC2=CC(Cl)=C(OC3=CC=C(Cl)C=C3)C=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

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Fenafluke

Cmax

ValueDoseCo-administeredAnalytePopulation
35.4 μg/mL
7.5 mg/kg single, oral
RAFOXANIDE plasma
Ovis aries
19750 OTHER
11.25 mg/kg bw single, oral
RAFOXANIDE plasma
Ovis aries

AUC

ValueDoseCo-administeredAnalytePopulation
413.5 μg × h/mL
7.5 mg/kg single, oral
RAFOXANIDE plasma
Ovis aries

T1/2

ValueDoseCo-administeredAnalytePopulation
7.5 day
7.5 mg/kg single, oral
RAFOXANIDE plasma
Ovis aries
8.9 day
11.25 mg/kg bw single, oral
RAFOXANIDE plasma
Ovis aries

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
11.25 mg/kg bw single, oral
RAFOXANIDE plasma
Ovis aries

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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