Rafoxanide

Basic Info

Common NameRafoxanide(F06222)
2D Structure
FRCD IDF06222
CAS Number22662-39-1
PubChem CID31475
FormulaC19H11Cl2I2NO3
IUPAC Name

N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3,5-diiodobenzamide

InChI Key

NEMNPWINWMHUMR-UHFFFAOYSA-N

InChI

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)

Canonical SMILES

C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=CC(=CC(=C3O)I)I)Cl)Cl

Isomeric SMILES

C1=CC(=CC=C1OC2=C(C=C(C=C2)NC(=O)C3=CC(=CC(=C3O)I)I)Cl)Cl

Synonyms
        
            Ranide, veterinary
        
            3'-Chloro-4'-(4-chlorophenoxy)-3,5-diiodosalicylanilide
        
            RAFOXANIDE
        
            22662-39-1
        
            Disalan
        
            Ranide
        
            Flukanide
        
            Bovanide
        
            Duofas
        
            MK-990
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassAnilides
Intermediate Tree NodesAromatic anilides
Direct ParentBenzanilides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzanilide - Diphenylether - Diaryl ether - Halobenzoic acid or derivatives - 3-halobenzoic acid or derivatives - Salicylic acid or derivatives - Salicylamide - Benzamide - Benzoic acid or derivatives - Phenoxy compound - Benzoyl - 4-halophenol - 2-halophenol - 2-iodophenol - 4-iodophenol - Phenol ether - Chlorobenzene - Halobenzene - Iodobenzene - Phenol - Aryl iodide - Aryl halide - Aryl chloride - Vinylogous acid - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Ether - Organochloride - Organic oxide - Hydrocarbon derivative - Organohalogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organoiodide - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Properties

Property NameProperty Value
Molecular Weight626.01
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Complexity507
Monoisotopic Mass624.821
Exact Mass624.821
XLogP7
Formal Charge0
Heavy Atom Count27
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9411
Human Intestinal AbsorptionHIA+0.9248
Caco-2 PermeabilityCaco2+0.5851
P-glycoprotein SubstrateNon-substrate0.8103
P-glycoprotein InhibitorNon-inhibitor0.8564
Non-inhibitor0.9058
Renal Organic Cation TransporterNon-inhibitor0.9040
Distribution
Subcellular localizationMitochondria0.8309
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7087
CYP450 2D6 SubstrateNon-substrate0.7731
CYP450 3A4 SubstrateNon-substrate0.5467
CYP450 1A2 InhibitorInhibitor0.7902
CYP450 2C9 InhibitorInhibitor0.6596
CYP450 2D6 InhibitorNon-inhibitor0.7541
CYP450 2C19 InhibitorNon-inhibitor0.5809
CYP450 3A4 InhibitorNon-inhibitor0.6886
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.8000
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9670
Non-inhibitor0.8190
AMES ToxicityNon AMES toxic0.7802
CarcinogensNon-carcinogens0.7256
Fish ToxicityHigh FHMT0.9406
Tetrahymena Pyriformis ToxicityHigh TPT0.9979
Honey Bee ToxicityLow HBT0.7592
BiodegradationNot ready biodegradable0.9922
Acute Oral ToxicityIII0.5433
Carcinogenicity (Three-class)Non-required0.5564
Model Value Unit
Absorption
Aqueous solubility-4.9865LogS
Caco-2 Permeability1.3539LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5796LD50, mol/kg
Fish Toxicity0.3299pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.7669pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cattle,Edible OffalJapan0.01ppm
Other Terrestrial Mammals,KidneyJapan0.2ppm
Cattle,KidneyJapan0.04ppm
Other Terrestrial Mammals,LiverJapan0.2ppm
Cattle,LiverJapan0.01ppm
Other Terrestrial Mammals,FatJapan0.3ppm
Cattle,FatJapan0.03ppm
Other Terrestrial Mammals,MuscleJapan0.1ppm
Cattle,MuscleJapan0.03ppm
Other Terrestrial Mammals,Edible OffalJapan0.2ppm

References

TitleJournalDatePubmed ID
[Determination of phenolic and salicylanilide anthelmintics in liquid milk byhigh performance liquid chromatography].Se Pu2013 Oct24432649
Stability during cooking of anthelmintic veterinary drug residues in beef.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Feb21240825
Determination of closantel and rafoxanide in animal tissues by online anionicmixed-mode solid-phase extraction followed by isotope dilution liquidchromatography tandem mass spectrometry.J Sep Sci2011 Jun21560244
Effect of three anthelmentics on disposition kinetics of florfenicol in goats.Food Chem Toxicol2010 Dec20863870
Experiments on anthelmintic control of Fasciola hepatica in Brazil.Vet Parasitol1992 Jul1413453