Praziquantel

Basic Info

Common NamePraziquantel(F06228)
2D Structure
FRCD IDF06228
CAS Number55268-74-1
PubChem CID4891
FormulaC19H24N2O2
IUPAC Name

2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one

InChI Key

FSVJFNAIGNNGKK-UHFFFAOYSA-N

InChI

InChI=1S/C19H24N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h4-6,9,15,17H,1-3,7-8,10-13H2

Canonical SMILES

C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2

Isomeric SMILES

C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2

Synonyms
        
            Biltricide
        
            Cutter Tape Tabs
        
            praziquantel
        
            55268-74-1
        
            Droncit
        
            Pyquiton
        
            Cesol
        
            Azinox
        
            Embay 8440
        
            Prasiquantel
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha-amino acid or derivatives - Tetrahydroisoquinoline - N-alkylpiperazine - 1,4-diazinane - Piperazine - Benzenoid - Tertiary carboxylic acid amide - Lactam - Carboxamide group - Carboxylic acid derivative - Azacycle - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Properties

Property NameProperty Value
Molecular Weight312.413
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity472
Monoisotopic Mass312.184
Exact Mass312.184
XLogP2.7
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9939
Human Intestinal AbsorptionHIA+0.9740
Caco-2 PermeabilityCaco2+0.5496
P-glycoprotein SubstrateSubstrate0.7237
P-glycoprotein InhibitorInhibitor0.8052
Non-inhibitor0.9113
Renal Organic Cation TransporterInhibitor0.5469
Distribution
Subcellular localizationMitochondria0.8077
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8505
CYP450 2D6 SubstrateSubstrate0.8918
CYP450 3A4 SubstrateSubstrate0.5805
CYP450 1A2 InhibitorInhibitor0.8460
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorInhibitor0.8994
CYP450 3A4 InhibitorNon-inhibitor0.8310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5401
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8291
Non-inhibitor0.5813
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.9637
Fish ToxicityLow FHMT0.9405
Tetrahymena Pyriformis ToxicityHigh TPT0.6334
Honey Bee ToxicityLow HBT0.8762
BiodegradationNot ready biodegradable0.9413
Acute Oral ToxicityIII0.7919
Carcinogenicity (Three-class)Non-required0.6930
Model Value Unit
Absorption
Aqueous solubility-2.7963LogS
Caco-2 Permeability1.1862LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0726LD50, mol/kg
Fish Toxicity2.1521pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1627pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry Animals,LiverJapan0.02ppm
HoneyJapan0.02ppm
Other Aquatic AnimalJapan0.02ppm
CrustaceansJapan0.02ppm
Shelled MolluscasJapan0.02ppm
Other FishJapan0.02ppm
PerciformesJapan0.02ppm
AnguilliformesJapan0.02ppm
SalmoniformesJapan0.02ppm
Other Poultry,EggsJapan0.02ppm
Chicken,EggsJapan0.02ppm
Other Poultry Animals,Edible OffalJapan0.02ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.02ppm
Chicken,KidneyJapan0.02ppm
Chicken,LiverJapan0.02ppm
Other Poultry Animals,FatJapan0.02ppm
Chicken,FatJapan0.02ppm
Other Poultry Animals,MuscleJapan0.02ppm
Chicken,MuscleJapan0.02ppm

References

TitleJournalDatePubmed ID
Distribution of Spiked Drugs between Milk Fat, Skim Milk, Whey, Curd, and MilkProtein Fractions: Expansion of Partitioning Models.J Agric Food Chem2018 Jan 1029271654
Efficacy of injectable praziquantel for elimination of trematode metacercariae inbluegills (Lepomis macrochirus) and quantification of parasite death by propidiumiodide staining.Parasitol Res2018 Feb29264719
Antiparasitic activity of nerolidol in a mouse model of schistosomiasis.Int J Antimicrob Agents2017 Sep28666754
Examination of the "susceptibility gap" in the treatment of canine heartworminfection.Parasit Vectors2017 Nov 929143689
Stray cats are more frequently infected with zoonotic protists than pet cats.Folia Parasitol (Praha)2017 Dec 629214976
A mysterious family of calcium-binding proteins from parasitic worms.Biochem Soc Trans2016 Aug 1527528745
Anthelmintic effects of the essential oil of fennel (Foeniculum vulgare Mill.,Apiaceae) against Schistosoma mansoni.Chem Biodivers2015 Jul26172330
Comparative biochemical analysis of three members of the Schistosoma mansoni TAL family: Differences in ion and drug binding properties.Biochimie2015 Jan25447146
Defining the Schistosoma haematobium kinome enables the prediction of essentialkinases as anti-schistosome drug targets.Sci Rep2015 Dec 426635209
Omega-1 knockdown in Schistosoma mansoni eggs by lentivirus transduction reduces granuloma size in vivo.Nat Commun2014 Nov 1725400038
Praziquantel form, dietary application method and dietary inclusion level affect palatability and efficacy against monogenean parasites in yellowtail kingfish.Dis Aquat Organ2014 May 1324991743
Phytol, a diterpene alcohol from chlorophyll, as a drug against neglectedtropical disease Schistosomiasis mansoni.PLoS Negl Trop Dis2014 Jan 224392173
Intestinal schistosomiasis in chimpanzees on Ngamba Island, Uganda: observations on liver fibrosis, schistosome genetic diversity and praziquantel treatment.Parasitology2013 Mar23095137
Anthelmintic activity of carvacryl acetate against Schistosoma mansoni.Parasitol Res2013 Feb23086444
Therapeutic efficacy of milbemycin oxime/praziquantel oral formulation(Milbemax®) against Thelazia callipaeda in naturally infested dogs and cats.Parasit Vectors2012 May 1922541136
Challenges for diagnosis and control of cystic hydatid disease.Acta Trop2012 Jul22410539
[Simultaneous determination of multi-veterinary drug residues in honey by solidphase extraction-high performance liquid chromatography-tandem massspectrometry].Se Pu2011 Jun22032165
Solid lipid extrusion with small die diameters--electrostatic charging, tastemasking and continuous production.Eur J Pharm Biopharm2011 Jan20940049
Multiple micronutrients including iron are not more effective than iron alone forimproving hemoglobin and iron status of Malian school children.J Nutr2009 Oct19675104
Care, husbandry and diseases of the African giant rat (Cricetomys gambianus).J S Afr Vet Assoc2008 Jun18846849