Levamisole

Basic Info

Common NameLevamisole(F06047)
2D Structure
FRCD IDF06047
CAS Number14769-73-4
PubChem CID26879
FormulaC11H12N2S
IUPAC Name

(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

InChI Key

HLFSDGLLUJUHTE-SNVBAGLBSA-N

InChI

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1

Canonical SMILES

C1CSC2=NC(CN21)C3=CC=CC=C3

Isomeric SMILES

C1CSC2=N[C@H](CN21)C3=CC=CC=C3

Synonyms
        
            Ergamisol
        
            levamisole
        
            14769-73-4
        
            Levamisol
        
            L-Tetramisole
        
            Wormicid
        
            Ketrax
        
            Lepuron
        
            Levamisolum
        
            LEVOMYSOL
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassImidazothiazoles
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentImidazothiazoles
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsImidazothiazole - Benzenoid - Monocyclic benzene moiety - Thiazolidine - 2-imidazoline - Isothiourea - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as imidazothiazoles. These are organic polycyclic compounds containing an imidazole ring fused to a thiazole ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Thiazole is a 6-membered ring that contains both sulfur and nitrogen.

Properties

Property NameProperty Value
Molecular Weight204.291
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity246
Monoisotopic Mass204.072
Exact Mass204.072
XLogP1.8
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count1
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+0.9513
Human Intestinal AbsorptionHIA+0.9868
Caco-2 PermeabilityCaco2+0.5286
P-glycoprotein SubstrateSubstrate0.6429
P-glycoprotein InhibitorNon-inhibitor0.7329
Non-inhibitor0.8382
Renal Organic Cation TransporterInhibitor0.7280
Distribution
Subcellular localizationLysosome0.4876
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8531
CYP450 2D6 SubstrateNon-substrate0.5639
CYP450 3A4 SubstrateNon-substrate0.7161
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorInhibitor0.8026
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.9238
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.8370
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7472
Non-inhibitor0.8734
AMES ToxicityNon AMES toxic0.6514
CarcinogensNon-carcinogens0.9350
Fish ToxicityHigh FHMT0.9471
Tetrahymena Pyriformis ToxicityHigh TPT0.9862
Honey Bee ToxicityLow HBT0.6265
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityII0.7295
Carcinogenicity (Three-class)Non-required0.6289
Model Value Unit
Absorption
Aqueous solubility-2.6793LogS
Caco-2 Permeability1.1116LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6601LD50, mol/kg
Fish Toxicity1.8877pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.2449pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,Kidney(Except Duck And Turkey)Japan0.01ppm
Other Poultry,EggsJapan1ppm
Chicken,EggsJapan1ppm
Other Poultry Animals,Edible OffalJapan0.06ppm
Chicken,Edible OffalJapan0.06ppm
Other Poultry Animals,Liver(Except Duck And Turkey)Japan0.1ppm
Other Poultry Animals,Fat(Except Duck And Turkey)Japan0.01ppm
Other Poultry Animals,Muscle(Except Duck And Turkey)Japan0.01ppm
MilkJapan0.3ppm
Other Terrestrial Mammals,Edible OffalJapan0.5ppm
Sheep,Edible OffalJapan0.3ppm
Pig,Edible OffalJapan0.3ppm
Cattle,Edible OffalJapan0.3ppm
Other Terrestrial Mammals,KidneyJapan0.5ppm
Other Terrestrial Mammals,LiverJapan0.6ppm
Other Terrestrial Mammals,FatJapan0.01ppm
Other Terrestrial Mammals,MuscleJapan0.06ppm
Turkey,KidneyJapan0.01ppm
Duck,KidneyJapan0.01ppm
Chicken,KidneyJapan0.01ppm

References

TitleJournalDatePubmed ID
Effect of thermal treatments on the degradation of antibiotic residues in food.Crit Rev Food Sci Nutr2017 Nov 2227052471
A nationwide survey of anthelmintic treatment failure on sheep farms in Ireland.Ir Vet J2017 Feb 928203368
Immunomodulatory activity of Buchholzia coriacea seed methanol extract onTrypanosoma brucei brucei infected mice.Pharm Biol2017 Dec27951754
In vitro anthelmintic effect of Tobacco (Nicotiana tabacum) extract on parasitic nematode, Marshallagia marshalli.J Parasit Dis2016 Sep27605759
Anthelmintic resistance in gastrointestinal nematodes of beef cattle in the stateof Rio Grande do Sul, Brazil.Int J Parasitol Drugs Drug Resist2016 Feb 827054068
Effect In Vitro of Antiparasitic Drugs on Microbial Inhibitor Test Responses for Screening Antibiotic Residues in Goat's Milk.J Food Prot2015 Sep26319732
Anthelmintic resistance in gastrointestinal nematodes from grazing beef cattle inCampeche State, Mexico.Trop Anim Health Prod2015 Aug25876195
Drug-efflux and target-site gene expression patterns in Haemonchus contortuslarvae able to survive increasing concentrations of levamisole in vitro.Int J Parasitol Drugs Drug Resist2014 Mar 1325057457
The effect of palm oil addition to the diet of dairy sheep on the immuneresponse.J Anim Physiol Anim Nutr (Berl)2014 Jun23751141
Acetylcholine receptor subunit and P-glycoprotein transcription patterns inlevamisole-susceptible and -resistant Haemonchus contortus.Int J Parasitol Drugs Drug Resist2013 Feb 124533293
The effects of levamisole on oxidative stress induced by copper intoxication inbroilers.N Z Vet J2012 Sep22621671
Development of an Evidence biochip array kit for the multiplex screening of more than 20 anthelmintic drugs.Anal Bioanal Chem2012 Jul22566198
Systemic treatments for cutaneous warts: a systematic review.J Dermatolog Treat2012 Feb21054194
Determination of levamisole in feeds by liquid chromatography coupled toelectrospray mass spectrometry on an ion trap.Rapid Commun Mass Spectrom2012 Apr 1522368052
Stability during cooking of anthelmintic veterinary drug residues in beef.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Feb21240825
The ameliorative and toxic effects of selenite on Caenorhabditis elegans.Food Chem Toxicol2011 Apr21145367
Between-habitat comparison of digestive enzymes activities and energy reserves inthe SW Atlantic euryhaline burrowing crab Neohelice granulata.Comp Biochem Physiol A Mol Integr Physiol2011 Apr21215323
In vivo anthelmintic activity of Azadirachta indica A. Juss seeds againstgastrointestinal nematodes of sheep.Vet Parasitol2010 Mar 2519963323
Determination of anthelmintic drug residues in milk using ultra high performance liquid chromatography-tandem mass spectrometry with rapid polarity switching.J Chromatogr A2010 Jul 220564781
Comparison of several extraction techniques for multiclass analysis of veterinarydrugs in eggs using ultra-high pressure liquid chromatography-tandem massspectrometry.Anal Chim Acta2010 Feb 2820113729