Oxyclozanide

Basic Info

Common NameOxyclozanide(F06114)
2D Structure
FRCD IDF06114
CAS Number2277-92-1
PubChem CID16779
FormulaC13H6Cl5NO3
IUPAC Name

2,3,5-trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide

InChI Key

JYWIYHUXVMAGLG-UHFFFAOYSA-N

InChI

InChI=1S/C13H6Cl5NO3/c14-4-1-6(16)11(20)8(2-4)19-13(22)9-10(18)5(15)3-7(17)12(9)21/h1-3,20-21H,(H,19,22)

Canonical SMILES

C1=C(C=C(C(=C1Cl)O)NC(=O)C2=C(C(=CC(=C2Cl)Cl)Cl)O)Cl

Isomeric SMILES

C1=C(C=C(C(=C1Cl)O)NC(=O)C2=C(C(=CC(=C2Cl)Cl)Cl)O)Cl

Synonyms
        
            2277-92-1
        
            2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide
        
            Oxyclozanide
        
            Oxiclozanidum
        
            Zanil
        
            Oxyclozanid
        
            Zanilox
        
            Diplin
        
            Oxyclozanide [INN:BAN]
        
            Oxyclozanidum [INN-Latin]
Classifies
                

                  
                    Predicted: Pesticide
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 - Salicylamide - Salicylic acid or derivatives - 2-halobenzoic acid or derivatives - 3-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Benzamide - Benzoic acid or derivatives - Benzoyl - 1,3-dichlorobenzene - 4-halophenol - 3-halophenol - 2-halophenol - 3-chlorophenol - 2-chlorophenol - 4-chlorophenol - Phenol - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Vinylogous halide - Vinylogous acid - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Organonitrogen compound - Organohalogen compound - Organochloride - Organopnictogen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen 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 Weight401.445
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity415
Monoisotopic Mass398.879
Exact Mass400.876
XLogP5.7
Formal Charge0
Heavy Atom Count22
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+0.7770
Human Intestinal AbsorptionHIA+0.9612
Caco-2 PermeabilityCaco2+0.6067
P-glycoprotein SubstrateNon-substrate0.7852
P-glycoprotein InhibitorNon-inhibitor0.9432
Non-inhibitor0.9715
Renal Organic Cation TransporterNon-inhibitor0.9378
Distribution
Subcellular localizationMitochondria0.8129
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7092
CYP450 2D6 SubstrateNon-substrate0.7923
CYP450 3A4 SubstrateNon-substrate0.5799
CYP450 1A2 InhibitorInhibitor0.8559
CYP450 2C9 InhibitorNon-inhibitor0.5638
CYP450 2D6 InhibitorNon-inhibitor0.7927
CYP450 2C19 InhibitorNon-inhibitor0.5122
CYP450 3A4 InhibitorNon-inhibitor0.6631
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6619
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9685
Non-inhibitor0.8639
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.7708
Fish ToxicityHigh FHMT0.9656
Tetrahymena Pyriformis ToxicityHigh TPT0.9976
Honey Bee ToxicityLow HBT0.8138
BiodegradationNot ready biodegradable0.9720
Acute Oral ToxicityIII0.7945
Carcinogenicity (Three-class)Non-required0.6875
Model Value Unit
Absorption
Aqueous solubility-4.6721LogS
Caco-2 Permeability1.1666LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5726LD50, mol/kg
Fish Toxicity0.3903pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9308pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.3ppm
Cattle,Edible OffalJapan0.5ppm
Other Terrestrial Mammals,KidneyJapan1ppm
Cattle,KidneyJapan0.5ppm
Other Terrestrial Mammals,LiverJapan1ppm
Cattle,LiverJapan0.5ppm
Other Terrestrial Mammals,FatJapan0.02ppm
Cattle,FatJapan0.5ppm
Other Terrestrial Mammals,MuscleJapan0.3ppm
Cattle,MuscleJapan0.1ppm
Other Terrestrial Mammals,Edible OffalJapan2ppm

References

TitleJournalDatePubmed ID
Repurposing salicylanilide anthelmintic drugs to combat drug resistant Staphylococcus aureus.PLoS One201525897961
[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
Point prevalence of bovine fascioliasis and the influence of chemotherapy on the milk yield in a lactating bovine population from the district of Toba Tek Singh, Pakistan.J Helminthol2011 Sep21062526
The comparative efficacy of four anthelmintics against a natural acquiredFasciola hepatica infection in hill sheep flock in the west of Ireland.Vet Parasitol2009 Oct 1419556063
Efficacy of oxyclozanide against the rumen fluke Calicophoron daubneyi inexperimentally infected goats.Vet J2009 May18314360
Responses in milk production to control of gastrointestinal nematode andparamphistome parasites in dairy cattle.Aust Vet J1996 Dec9006864
Control of selenium and cobalt deficiency in lambs by supplementation of oralanthelmintics.Vet Rec1988 Aug 273176281