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Identification
NamePraziquantel
Accession NumberDB01058  (APRD01196, EXPT02728)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

An anthelmintic used in most schistosome and many cestode infestations. [PubChem]

Structure
Thumb
Synonyms
Biltricide
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Biltricidetablet, film coated600 mg/1oralBayer Health Care Pharmaceuticals Inc.2011-04-21Not applicableUs
Biltricidetablet600 mgoralBayer Inc1997-04-24Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6490C9U457
CAS number55268-74-1
WeightAverage: 312.4061
Monoisotopic: 312.183778022
Chemical FormulaC19H24N2O2
InChI KeyInChIKey=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
IUPAC Name
2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
SMILES
O=C(C1CCCCC1)N1CC2N(CCC3=CC=CC=C23)C(=O)C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • N-alkylpiperazine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Tertiary carboxylic acid amide
  • Cyclic alcohol
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of infections due to all species of schistosoma.
PharmacodynamicsPraziquantel is an anthelmintic used in most schistosome and many cestode infestations. Praziquantel effects the permeability of the cell membrane resulting in the contraction of schistosomes. The drug further causes vacuolization and disintegration of the schistosome tegument. The effect is more marked on adult worms compared to young worms. An increased calcium influx may play an important role. Secondary effects are inhibition of glucose uptake, lowering of glycogen levels and stimulation of lactate release. The action of praziquantel is limited very specifically to trematodes and cestodes; nematodes (including filariae) are not affected.
Mechanism of actionPraziquantel works by causing severe spasms and paralysis of the worms' muscles. This paralysis is accompanied - and probably caused - by a rapid Ca 2+ influx inside the schistosome. Morphological alterations are another early effect of praziquantel. These morphological alterations are accompanied by an increased exposure of schistosome antigens at the parasite surface. The worms are then either completely destroyed in the intestine or passed in the stool. An interesting quirk of praziquantel is that it is relatively ineffective against juvenile schistosomes. While initially effective, effectiveness against schistosomes decreases until it reaches a minimum at 3-4 weeks. Effectiveness then increases again until it is once again fully effective at 6-7 weeks. Glutathione S-transferase (GST), an essential detoxification enzyme in parasitic helminths, is a major vaccine target and a drug target against schistosomiasis. Schistosome calcium ion channels are currently the only known target of praziquantel.
Related Articles
AbsorptionRapidly absorbed (80%)
Volume of distributionNot Available
Protein binding80 to 85%
Metabolism

renal

Route of eliminationNot Available
Half life0.8-1.5 hours (in serum)
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.974
Blood Brain Barrier+0.9939
Caco-2 permeable+0.5496
P-glycoprotein substrateSubstrate0.7237
P-glycoprotein inhibitor IInhibitor0.8052
P-glycoprotein inhibitor IINon-inhibitor0.9113
Renal organic cation transporterInhibitor0.5469
CYP450 2C9 substrateNon-substrate0.8505
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5805
CYP450 1A2 substrateInhibitor0.846
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5401
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9637
BiodegradationNot ready biodegradable0.9413
Rat acute toxicity2.0726 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8291
hERG inhibition (predictor II)Non-inhibitor0.5813
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral600 mg
Tablet, film coatedoral600 mg/1
Prices
Unit descriptionCostUnit
Biltricide 600 mg tablet14.57USD tablet
Praziquantel powder1.06USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point136 °CPhysProp
water solubility400 mg/LMERCK INDEX (1996)
logP2.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.381 mg/mLALOGPS
logP2.42ALOGPS
logP2.3ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.79 m3·mol-1ChemAxon
Polarizability34.84 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. doi: 10.1097/QCO.0b013e328318978f. [PubMed:18978535 ]
  2. McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. doi: 10.1128/CMR.00046-07. [PubMed:18202444 ]
External Links
ATC CodesP02BA01
AHFS Codes
  • 08:08.00
PDB Entries
FDA labelDownload (152 KB)
MSDSDownload (72.4 KB)
Interactions
Drug Interactions
Drug
AprepitantThe serum concentration of Praziquantel can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Praziquantel.
BexaroteneThe serum concentration of Praziquantel can be decreased when it is combined with Bexarotene.
BosentanThe serum concentration of Praziquantel can be decreased when it is combined with Bosentan.
CarbamazepineThe serum concentration of Praziquantel can be decreased when it is combined with Carbamazepine.
ChloroquineThe serum concentration of Praziquantel can be decreased when it is combined with Chloroquine.
CimetidineThe serum concentration of Praziquantel can be increased when it is combined with Cimetidine.
ConivaptanThe serum concentration of Praziquantel can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Praziquantel can be decreased when it is combined with Dabrafenib.
DasatinibThe serum concentration of Praziquantel can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Praziquantel can be decreased when it is combined with Deferasirox.
EnzalutamideThe serum concentration of Praziquantel can be decreased when it is combined with Enzalutamide.
FluconazoleThe metabolism of Praziquantel can be decreased when combined with Fluconazole.
FosaprepitantThe serum concentration of Praziquantel can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Praziquantel can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Praziquantel can be increased when it is combined with Fusidic Acid.
IdelalisibThe serum concentration of Praziquantel can be increased when it is combined with Idelalisib.
IvacaftorThe serum concentration of Praziquantel can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Praziquantel can be increased when it is combined with Ketoconazole.
LuliconazoleThe serum concentration of Praziquantel can be increased when it is combined with Luliconazole.
MifepristoneThe serum concentration of Praziquantel can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Praziquantel can be decreased when it is combined with Mitotane.
NelfinavirThe metabolism of Praziquantel can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Praziquantel can be increased when it is combined with Netupitant.
PalbociclibThe serum concentration of Praziquantel can be increased when it is combined with Palbociclib.
PhenobarbitalThe serum concentration of Praziquantel can be decreased when it is combined with Phenobarbital.
PhenytoinThe serum concentration of Praziquantel can be decreased when it is combined with Phenytoin.
PrimidoneThe serum concentration of Praziquantel can be decreased when it is combined with Primidone.
RifabutinThe serum concentration of Praziquantel can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Praziquantel can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Praziquantel can be decreased when it is combined with Rifapentine.
SiltuximabThe serum concentration of Praziquantel can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Praziquantel can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of Praziquantel can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Praziquantel can be increased when it is combined with Stiripentol.
TocilizumabThe serum concentration of Praziquantel can be decreased when it is combined with Tocilizumab.
Food Interactions
  • Grapefruit and grapefruit juice should be avoided throughout treatment. Grapefruit can increase serum levels of this product.
  • Take with food.

Targets

1. Schistosome calcium ion (Ca2+) channels
Kind
Group
Organism
Schistosoma
Pharmacological action
yes
Actions
other/unknown
References
  1. Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. doi: 10.1097/QCO.0b013e328318978f. [PubMed:18978535 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Monooxygenase activity
Specific Function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular Weight:
57669.21 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23