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Details

Stereochemistry RACEMIC
Molecular Formula C19H24N2O2
Molecular Weight 312.4061
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAZIQUANTEL

SMILES

O=C(C1CCCCC1)N2CC3N(CCC4=C3C=CC=C4)C(=O)C2

InChI

InChIKey=FSVJFNAIGNNGKK-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C19H24N2O2
Molecular Weight 312.4061
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Praziquantel, marketed as Biltricide, is an anthelmintic used in humans and animals for the treatment of tapeworms and flukes. Specifically, it is effective against schistosoma, Clonorchis sinensis the fish tape worm Diphyllobothrium latum. 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. The antibiotic rifampicin decreases plasma concentrations of praziquantel. Carbamazepine and phenytoin are reported to reduce the bioavailability of praziquantel. Chloroquine reduces the bioavailability of praziquantel. The drug cimetidine heightens praziquantel bioavailability.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BILTRICIDE
Curative
BILTRICIDE
Curative
BILTRICIDE
Curative
BILTRICIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
0.83 μg/mL
40 mg/kg single, oral
PRAZIQUANTEL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3.02 μg × h/mL
40 mg/kg single, oral
PRAZIQUANTEL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.99 h
40 mg/kg single, oral
PRAZIQUANTEL plasma
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
For schistosomiasis: 20 mg/kg body weight three times a day as a one day treatment, at intervals of not less than 4 hours and not more than 6 hours.
Route of Administration: Oral
In Vitro Use Guide
To discern whether stage-specific resistance of Schistosoma mansoni to praziquantel occurs in vitro, was determined minimal effective concentrations (MECs) of drug needed to increase motor activity, produce contraction and/or paralysis, and cause tegumental vesiculation of developmental stages from day 0 to day 42 of S. mansoni. Recovery of these stages from exposure to praziquantel in vitro was also evaluated. MECs of praziquantel inducing increased motor activity and muscular contraction or paralysis or both were 0.005-0.01 ug/ml, irrespective of the stage examined.
Substance Class Chemical
Record UNII
6490C9U457
Record Status Validated (UNII)
Record Version