Praziquantel

Identification

Summary

Praziquantel is an anthelmintic medication used to treat a number of parasitic worm infections such as schistosomiasis.

Brand Names
Biltricide
Generic Name
Praziquantel
DrugBank Accession Number
DB01058
Background

An anthelmintic used in most schistosome and many cestode infestations.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 312.4061
Monoisotopic: 312.183778022
Chemical Formula
C19H24N2O2
Synonyms
  • Praziquantel

Pharmacology

Indication

For the treatment of infections due to all species of schistosoma.

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Associated Conditions
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Pharmacodynamics

Praziquantel 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 action

Praziquantel 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.

TargetActionsOrganism
ASchistosome calcium ion (Ca2+) channels
other/unknown
Schistosoma
Absorption

Rapidly absorbed (80%)

Volume of distribution

Not Available

Protein binding

80 to 85%

Metabolism

renal

Route of elimination

Not Available

Half-life

0.8-1.5 hours (in serum)

Clearance

Not Available

Adverse Effects
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Toxicity

The acute toxicity of praziquantel is relatively low, as demonstrated by oral LD50 values ranging between 200 - 2976 mg/kg in various species.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Praziquantel can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Praziquantel can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Praziquantel can be increased when it is combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Praziquantel.
AcalabrutinibThe metabolism of Praziquantel can be decreased when combined with Acalabrutinib.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Praziquantel.
AcetaminophenThe metabolism of Praziquantel can be decreased when combined with Acetaminophen.
AcyclovirThe metabolism of Praziquantel can be decreased when combined with Acyclovir.
AdalimumabThe metabolism of Praziquantel can be increased when combined with Adalimumab.
AgomelatineThe metabolism of Agomelatine can be decreased when combined with Praziquantel.
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Food Interactions
  • Avoid grapefruit products.
  • Take with food.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BiltricideTablet, film coated600 mg/1OralAvera McKennan Hospital2015-05-272017-05-24US flag
BiltricideTablet, film coated600 mg/1OralDepartment Of State Health Services, Pharmacy Branch2016-11-182017-05-31US flag
BiltricideTablet, film coated600 mg/1OralBayer HealthCare Pharmaceuticals Inc.2011-04-21Not applicableUS flag
BiltricideTablet, film coated600 mg/1OralCentral Texas Community Health Centers2011-04-21Not applicableUS flag
BiltricideTablet600 mgOralBayer1997-04-24Not applicableCanada flag
BiltricideTablet, film coated600 mg/1OralSchering Corporation2010-08-162013-07-16US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PraziquantelTablet, film coated600 mg/1OralPar Pharmaceutical, Inc.2017-11-27Not applicableUS flag

Categories

ATC Codes
P02BA01 — Praziquantel
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrahydroisoquinolines
Sub Class
Not Available
Direct Parent
Tetrahydroisoquinolines
Alternative Parents
Alpha amino acids and derivatives / N-alkylpiperazines / Benzenoids / Tertiary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1,4-diazinane / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative / Lactam
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6490C9U457
CAS number
55268-74-1
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
IUPAC Name
2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-pyrazino[2,1-a]isoquinolin-4-one
SMILES
O=C(C1CCCCC1)N1CC2N(CCC3=CC=CC=C23)C(=O)C1

References

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. [Article]
  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. [Article]
  3. FDA Approved Drug Products: Biltricide (praziquantel) tablets [Link]
  4. Health Canada Product Monograph: Biltricide (praziquantel) tablets for oral use [Link]
Human Metabolome Database
HMDB0015191
KEGG Drug
D00471
KEGG Compound
C07367
PubChem Compound
4891
PubChem Substance
46507082
ChemSpider
4722
BindingDB
74574
RxNav
8628
ChEBI
91583
ChEMBL
CHEMBL976
Therapeutic Targets Database
DAP000695
PharmGKB
PA164764583
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Praziquantel
FDA label
Download (152 KB)
MSDS
Download (72.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections / Schistosomiasis Mansoni1
4CompletedTreatmentSchistosomiasis Mansoni1
4Unknown StatusPreventionAnemia / Change in Sustained Attention / Helminthiasis / Malaria / Schistosoma infection1
4WithdrawnBasic ScienceSchistosoma infection1
3CompletedPreventionHealthy Subjects (HS)1
3CompletedTreatmentSchistosoma Haematobium / Schistosoma Mansoni1
3CompletedTreatmentSchistosoma Hematobium Infection / Schistosomiasis Mansoni1
3CompletedTreatmentSchistosoma infection3
3CompletedTreatmentSchistosoma Mansoni1
3RecruitingDiagnosticDiagnostics / Drug Reaction / Pregnancy / Schistosomiasis Hematobium1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bayer Healthcare
  • Gallipot
  • KVP Pharma Plus Veterinaer Produkte GmbH
  • Schering Corp.
Dosage Forms
FormRouteStrength
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral600 mg
PasteOral
Tablet, coatedOral600 mg
PowderNot applicable1 g/1g
TabletOral600 mg
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136 °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)-0.6Chemaxon
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0019000000-066af1bbcb832fac2ff4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0092000000-2572aab54fdc9ff2617e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0790000000-bba67a778d41524cdf76
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00e9-0910000000-412442e38f79438b5893
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0089-0900000000-b663739905edd86c61cb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ik9-0049000000-02c2bbc25fcb21061ef8
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-2190000000-eca5b2601627401a5544
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f89-8980000000-5102a741f0625afd5c7a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-5910000000-2a141277a2d28d23bfd0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-4900000000-77a7f036670b581c354c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-3900000000-21cde0d9fc368991b837
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0019000000-9fdf91e83d7fd02342cc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0092000000-0dbdbc1e5a8153d5764a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0490000000-472ed6570d02d80aef23
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fl0-0920000000-4b4b7e731ba9ab20d076
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0089-0900000000-c5ff862373e835bc247f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0w29-0598000000-5f9aeabd10ef70166cb6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ik9-2698000000-8cf56d1fd2138bc420ec

Targets

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insights and accelerate drug research.
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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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data supported by in vitro studies.
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
Kind
Protein
Organism
Humans
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
References
  1. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Godawska-Matysik A, Kiec-Kononowicz K: Biotransformation of praziquantel by human cytochrome p450 3A4 (CYP 3A4). Acta Pol Pharm. 2006 Sep-Oct;63(5):381-5. [Article]
  2. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Punyo J, Sunbhanich M: Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13. doi: 10.1067/mcp.2002.129319. [Article]
  3. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 21, 2023 08:43