Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:10 UTC
HMDB IDHMDB15191
Secondary Accession NumbersNone
Metabolite Identification
Common NamePraziquantel
DescriptionPraziquantel is only found in individuals that have used or taken this drug. It is an anthelmintic used in most schistosome and many cestode infestations. [PubChem]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.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H24N2O2
Average Molecular Weight312.4061
Monoisotopic Molecular Weight312.183778022
IUPAC Name2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
Traditional IUPAC Namepraziquantel
CAS Registry Number55268-74-1
SMILES
O=C(C1CCCCC1)N1CC2N(CCC3=CC=CC=C23)C(=O)C1
InChI Identifier
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
InChI KeyFSVJFNAIGNNGKK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIsoquinolines
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxamide Group
  • Cyclic Alcohol
  • Cyclohexane
  • Lactam
  • Piperazine
  • Tertiary Carboxylic Acid Amide
Direct ParentIsoquinolines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.81e-01 g/LNot Available
LogP2.5Not Available
Predicted Properties
PropertyValueSource
water solubility0.38 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
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01058
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01058
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01058
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4722
KEGG Compound IDC07367
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPraziquantel
NuGOwiki LinkHMDB15191
Metagene LinkHMDB15191
METLIN IDNot Available
PubChem Compound4891
PDB IDNot Available
ChEBI ID199024
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. 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

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP1A2
Uniprot ID:
P05177