Human Metabolome Database Version 3.5

Showing metabocard for Praziquantel (HMDB15191)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:10 -0700
HMDB ID HMDB15191
Secondary Accession Numbers None
Metabolite Identification
Common Name Praziquantel
Description Praziquantel 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C19H24N2O2
Average Molecular Weight 312.4061
Monoisotopic Molecular Weight 312.183778022
IUPAC Name 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
Traditional IUPAC Name praziquantel
CAS Registry Number 55268-74-1
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 Key FSVJFNAIGNNGKK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Isoquinolines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxamide Group
  • Cyclic Alcohol
  • Cyclohexane
  • Lactam
  • Piperazine
  • Tertiary Carboxylic Acid Amide
Direct Parent Isoquinolines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 136 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.81e-01 g/L Not Available
LogP 2.5 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.38 g/L ALOGPS
LogP 2.42 ALOGPS
LogP 2.3 ChemAxon
LogS -2.91 ALOGPS
pKa (strongest acidic) 19.38 ChemAxon
pKa (strongest basic) -0.22 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 40.62 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 88.79 ChemAxon
Polarizability 34.84 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01058
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01058
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01058 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4722 Link_out
KEGG Compound ID C07367 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Praziquantel Link_out
NuGOwiki Link HMDB15191 Link_out
Metagene Link HMDB15191 Link_out
METLIN ID Not Available
PubChem Compound 4891 Link_out
PDB ID Not Available
ChEBI ID 199024 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA