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
Structure for Praziquantel (DB01058)
- 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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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism ASchistosome calcium ion (Ca2+) channels other/unknownSchistosoma - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Praziquantel can be increased when it is combined with Abametapir. Abatacept The metabolism of Praziquantel can be increased when combined with Abatacept. Abiraterone The serum concentration of Praziquantel can be increased when it is combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Praziquantel. Acalabrutinib The metabolism of Praziquantel can be decreased when combined with Acalabrutinib. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Praziquantel. Acetaminophen The metabolism of Praziquantel can be decreased when combined with Acetaminophen. Acyclovir The metabolism of Praziquantel can be decreased when combined with Acyclovir. Adalimumab The metabolism of Praziquantel can be increased when combined with Adalimumab. Agomelatine The metabolism of Agomelatine can be decreased when combined with Praziquantel. 
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- Avoid grapefruit products.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Biltricide Tablet, film coated 600 mg/1 Oral Avera McKennan Hospital 2015-05-27 2017-05-24 US 
Biltricide Tablet, film coated 600 mg/1 Oral Department Of State Health Services, Pharmacy Branch 2016-11-18 2017-05-31 US Biltricide Tablet, film coated 600 mg/1 Oral Bayer HealthCare Pharmaceuticals Inc. 2011-04-21 Not applicable US Biltricide Tablet, film coated 600 mg/1 Oral Central Texas Community Health Centers 2011-04-21 Not applicable US Biltricide Tablet 600 mg Oral Bayer 1997-04-24 Not applicable Canada 
Biltricide Tablet, film coated 600 mg/1 Oral Schering Corporation 2010-08-16 2013-07-16 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Praziquantel Tablet, film coated 600 mg/1 Oral Par Pharmaceutical, Inc. 2017-11-27 Not applicable US
Categories
- ATC Codes
- P02BA01 — Praziquantel
- Drug Categories
- Anthelmintics
- Anti-Infective Agents
- Antihelminthic
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antitrematodals
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Quinoline Derivatives and Related Substances
- 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
- 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]
- 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]
- FDA Approved Drug Products: Biltricide (praziquantel) tablets [Link]
- Health Canada Product Monograph: Biltricide (praziquantel) tablets for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0015191
- KEGG Drug
- D00471
- KEGG Compound
- C07367
- PubChem Compound
- 4891
- PubChem Substance
- 46507082
- ChemSpider
- 4722
- BindingDB
- 74574
- 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
Phase Status Purpose Conditions Count 4 Completed Basic Science Human Immunodeficiency Virus (HIV) Infections / Schistosomiasis Mansoni 1 4 Completed Treatment Schistosomiasis Mansoni 1 4 Unknown Status Prevention Anemia / Change in Sustained Attention / Helminthiasis / Malaria / Schistosoma infection 1 4 Withdrawn Basic Science Schistosoma infection 1 3 Completed Prevention Healthy Subjects (HS) 1 3 Completed Treatment Schistosoma Haematobium / Schistosoma Mansoni 1 3 Completed Treatment Schistosoma Hematobium Infection / Schistosomiasis Mansoni 1 3 Completed Treatment Schistosoma infection 3 3 Completed Treatment Schistosoma Mansoni 1 3 Recruiting Diagnostic Diagnostics / Drug Reaction / Pregnancy / Schistosomiasis Hematobium 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bayer Healthcare
- Gallipot
- KVP Pharma Plus Veterinaer Produkte GmbH
- Schering Corp.
- Dosage Forms
Form Route Strength Tablet, film coated Oral 600 mg/1 Tablet, film coated Oral 600 mg Paste Oral Tablet, coated Oral 600 mg Powder Not applicable 1 g/1g Tablet Oral 600 mg - Prices
Unit description Cost Unit Biltricide 600 mg tablet 14.57USD tablet Praziquantel powder 1.06USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 136 °C PhysProp water solubility 400 mg/L MERCK INDEX (1996) logP 2.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.381 mg/mL ALOGPS logP 2.42 ALOGPS logP 2.3 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 19.38 Chemaxon pKa (Strongest Basic) -0.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 40.62 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 88.79 m3·mol-1 Chemaxon Polarizability 34.84 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.974 Blood Brain Barrier + 0.9939 Caco-2 permeable + 0.5496 P-glycoprotein substrate Substrate 0.7237 P-glycoprotein inhibitor I Inhibitor 0.8052 P-glycoprotein inhibitor II Non-inhibitor 0.9113 Renal organic cation transporter Inhibitor 0.5469 CYP450 2C9 substrate Non-substrate 0.8505 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.5805 CYP450 1A2 substrate Inhibitor 0.846 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5401 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9637 Biodegradation Not ready biodegradable 0.9413 Rat acute toxicity 2.0726 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8291 hERG inhibition (predictor II) Non-inhibitor 0.5813
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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1. Schistosome calcium ion (Ca2+) channels
Yes
Other/unknown
References
- 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
- 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
- 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
- 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
- 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
- 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
- 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]
- 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]
- 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