You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePraziquantel
Accession NumberDB01058  (APRD01196, EXPT02728)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
BiltricideNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
BiltricideNot Available
Brand mixtures
Brand NameIngredients
Drontal - TabPraziquantel + Pyrantel (Pyrantel Pamoate)
Drontal Plus Tablets for Med. And Large DogsFebantel + Praziquantel + Pyrantel (Pyrantel Pamoate)
Drontal Plus Tablets for Small DogsFebantel + Praziquantel + Pyrantel (Pyrantel Pamoate)
Drontal Plus Tabs for Medium and Large DogsFebantel + Praziquantel + Pyrantel (Pyrantel Pamoate)
Drontal TabPraziquantel + Pyrantel (Pyrantel Pamoate)
CategoriesNot Available
CAS number55268-74-1
WeightAverage: 312.4061
Monoisotopic: 312.183778022
Chemical FormulaC19H24N2O2
InChI KeyFSVJFNAIGNNGKK-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIsoquinolines and Derivatives
SubclassNot Available
Direct parentIsoquinolines and Derivatives
Alternative parentsBenzene and Substituted Derivatives; Diazinanes; Piperazines; Tertiary Carboxylic Acid Amides; Cyclic Alcohols and Derivatives; Tertiary Amines; Polyamines; Carboxylic Acids; Enolates
Substituents1,4-diazinane; benzene; piperazine; cyclic alcohol; tertiary carboxylic acid amide; carboxamide group; tertiary amine; carboxylic acid derivative; polyamine; carboxylic acid; enolate; organonitrogen compound; amine
Classification descriptionThis compound belongs to the isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
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.
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
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
Prices
Unit descriptionCostUnit
Biltricide 600 mg tablet14.57USDtablet
Praziquantel powder1.06USDg
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 solubility3.81e-01 g/lALOGPS
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 area40.62ChemAxon
rotatable bond count1ChemAxon
refractivity88.79ChemAxon
polarizability34.84ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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. Pubmed
  2. McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. Pubmed
External Links
ResourceLink
KEGG DrugD00471
KEGG CompoundC07367
PubChem Compound4891
PubChem Substance46507082
ChemSpider4722
Therapeutic Targets DatabaseDAP000695
PharmGKBPA164764583
HETPZQ
Drug Product Database2230897
RxListhttp://www.rxlist.com/cgi/generic2/praziquantel.htm
Drugs.comhttp://www.drugs.com/cdi/praziquantel.html
WikipediaPraziquantel
ATC CodesP02BA01
AHFS Codes
  • 08:08.00
PDB Entries
FDA labelshow(152 KB)
MSDSshow(72.4 KB)
Interactions
Drug Interactions
Drug
CarbamazepineMarkedly lower praziquantel levels
ChloroquineMarkedly lower praziquantel levels
EtravirinePraziquantel, when used concomitantly with etravirine (a strong CYP3A4 inducer), may experience a decrease in serum concentration. It is recommended to avoid concurrent therapy.
EtravirinePraziquantel, when used concomitantly with etravirine (a strong CYP3A4 inducer), may experience a decrease in serum concentration. It is recommended to avoid concurrent therapy.
PhenytoinMarkedly lower praziquantel levels
RifampicinSignificant decrease in praziquantel level
TelithromycinTelithromycin may reduce clearance of Praziquantel. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Praziquantel if Telithromycin is initiated, discontinued or dose changed.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of praziquantel by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of praziquantel if voriconazole is initiated, discontinued or dose changed.
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

Components

Name UniProt ID Details

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. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 3A43

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A43 Q9HB55 Details

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. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

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. Epub 2009 Nov 24. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13