U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=CC=CC=C34)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

Description
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/018714s013lbl.pdf https://en.wikipedia.org/wiki/Praziquantel

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

Curator's Comment: Praziquantel permeates the blood-brain barrier, thus explaining its effectiveness on parenchymal brain cysticercosis. Plasma concentrations of the drug are increased when a high carbohydrate diet is administered.

Originator

Curator's Comment: # in the laboratories of Bayer AG and Merck KGaA

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BILTRICIDE

Approved Use

for the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated

Launch Date

1984
Curative
BILTRICIDE

Approved Use

for the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated

Launch Date

1984
Curative
BILTRICIDE

Approved Use

for the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated

Launch Date

1984
Curative
BILTRICIDE

Approved Use

for the treatment of infections due to: all species of schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini (approval of this indication was based on studies in which the two species were not differentiated

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.2 μg/mL
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (R)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.9 μg/mL
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (S)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.83 μg/mL
40 mg/kg single, oral
dose: 40 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZIQUANTEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.1 μg × h/mL
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (R)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9 μg × h/mL
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (S)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.02 μg × h/mL
40 mg/kg single, oral
dose: 40 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZIQUANTEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.1 h
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (R)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.3 h
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (S)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.99 h
40 mg/kg single, oral
dose: 40 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZIQUANTEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
25 mg/kg 3 times / day multiple, oral
dose: 25 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PRAZIQUANTEL, (S)- plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1800 mg single, oral
Studied dose
Dose: 1800 mg
Route: oral
Route: single
Dose: 1800 mg
Sources:
healthy, 26 - 47
Health Status: healthy
Age Group: 26 - 47
Sources:
100 mg/kg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg/kg, 1 times / day
Sources:
unhealthy, 32 ± 15
Health Status: unhealthy
Age Group: 32 ± 15
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Control of Echinococcus granulosus in Uruguay: evaluation of different treatment intervals for dogs.
2002-02-04
The effect of Nigella sativa oil against the liver damage induced by Schistosoma mansoni infection in mice.
2002-01
Evidence against rapid emergence of praziquantel resistance in Schistosoma haematobium, Kenya.
2001-12-19
Diphyllobothrium latum infection after eating domestic salmon flesh.
2001-12
Control of clonorchiasis by repeated treatments with praziquantel.
2001-12
Current progress in the development and use of artemether for chemoprophylaxis of major human schistosome parasites.
2001-12
Acidic vesicles of Schistosoma mansoni.
2001-12
The potential of artemether for the control of schistosomiasis.
2001-12
Isolation and identification of 8-hydroxypraziquantel as a metabolite of the antischistosomal drug praziquantel.
2001-12
Optimization of the single-day praziquantel therapy for neurocysticercosis.
2001-11-27
Development and validation of a 'tablet pole' for the administration of praziquantel in sub-Saharan Africa.
2001-11-15
Efficacy of praziquantel against Schistosoma japonicum: field evaluation in an area with repeated chemotherapy compared with a newly identified endemic focus in Hunan, China.
2001-11-15
Artesunate and praziquantel for the treatment of Schistosoma haematobium infections: a double-blind, randomized, placebo-controlled study.
2001-11-15
[Tactics of wide use of praziquantel in the complex of measures for prevention of opisthorchiasis. 3. General approach for ambulatory treatment of patients with opisthorchiasis in disease reservoirs].
2001-11-13
Just another hemoptysis or a fluke?
2001-11
Urinary schistosomiasis in southern Ghana: a logistic regression approach to data from a community-based integrated control program.
2001-11
Are poor responses to praziquantel for the treatment of Schistosoma mansoni infections in Senegal due to resistance? An overview of the evidence.
2001-11
Impact of schistosomiasis on patient and graft outcome after renal transplantation: 10 years' follow-up.
2001-11
Prospects in medical management of Echinococcus granulosus.
2001-10-27
[Anemia, eosinophilia and generalized weakness in a 20-year old African].
2001-10-15
Human susceptibility to Schistosoma japonicum in China correlates with antibody isotypes to native antigens.
2001-10-03
[Subretinal granuloma, retinal vasculitis and keratouveitis with secondary open-angle glaucoma in schistosomiasis].
2001-10
A baseline study on the importance of bovines for human Schistosoma japonicum infection around Poyang Lake, China.
2001-10
Reinfection with Schistosoma haematobium following school-based chemotherapy with praziquantel in four highly endemic villages in Côte d'Ivoire.
2001-10
Acute colonic obstruction due to schistosomiasis in conjunction with ingestion of mangos.
2001-10
Failure of one-day praziquantel treatment in patients with multiple neurocysticercosis lesions.
2001-10
Medical treatment for neurocysticercosis characterized by giant subarachnoid cysts.
2001-09-20
Tropical warts.
2001-09-08
Spinal-cord involvement in the hepato-splenic form of Schistosoma mansoni infection.
2001-09
Combined praziquantel and albendazole chemoprophylaxis in experimental hydatidosis.
2001-09
Susceptibility of Schistosoma japonicum to praziquantel in China.
2001-09
In vitro effects of isoprinosine and a dipeptide methyl ester on Echinococcus multilocularis protoscoleces.
2001-09
In vitro responses of praziquantel-resistant and -susceptible Schistosoma mansoni to praziquantel.
2001-09
Counterfeit praziquantel.
2001-08-25
Depletion of praziquantel in plasma and muscle tissue of cultured rockfish Sebastes schlegeli after oral and bath treatment.
2001-08-02
Praziquantel--quality, dosages and markers of resistance.
2001-08
Pharmacokinetics and microsomal oxidation of praziquantel and its effects on the P450 system in three-month-old lambs infested by Fasciola hepatica.
2001-08
Acanthoparyphium tyosenense: the discovery of human infection and identification of its source.
2001-08
A rare case of eosinophilic pleuritis due to sparganosis.
2001-08
A comparative trial of albendazole alone versus combination of albendazole and praziquantel for treatment of Trichuris trichiura infection.
2001-06
Schistosoma mansoni and Biomphalaria: past history and future trends.
2001
[Schistosomiasis of the spinal cord. Case report].
2001
Primary hydatid cyst of the axillary region: report of a case.
2001
Replacing oxamniquine by praziquantel against Schistosoma mansoni infection in a rural community from the sugar-cane zone of Northeast Brazil: an epidemiological follow-up.
2001
The impact of repeated treatment with praziquantel of schistosomiasis in children under six years of age living in an endemic area for Schistosoma haematobium infection.
2001
T cell clones from Schistosoma haematobium infected and exposed individuals lacking distinct cytokine profiles for Th1/Th2 polarisation.
2001
Schistosomiasis epidemiology and control: how did we get here and where should we go?
2001
Voltammetric determination of praziquantel in tablets and biological fluids.
2001
Evaluation of efficacy of school-based anthelmintic treatments against anaemia in children in the United Republic of Tanzania.
2001
Optimising the benefits of anthelmintic treatment in children.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The recommended dose for clonorchiasis and opisthorchiasis is: 25 mg/kg bodyweight three times a day as a one day treatment, at intervals of not less than 4 hours and not more than 6 hours. The tablets should be washed down unchewed with water during meals.
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.
Name Type Language
BILTRICIDE
Preferred Name English
PRAZIQUANTEL
INN   USAN  
Official Name English
PRAZIQUANTEL [VANDF]
Common Name English
EMBAY-8440
Code English
PRAZIQUANTEL [ORANGE BOOK]
Common Name English
PRAZIQUANTEL [MI]
Common Name English
PROFENDER COMPONENT PRAZIQUANTEL
Brand Name English
PRAZIQUANTEL [USP-RS]
Common Name English
Praziquantel [WHO-DD]
Common Name English
PRAZIQUANTEL [MART.]
Common Name English
BROADLINE COMPONENT PRAZIQUANTEL
Brand Name English
PRAZIQUANTEL [USP IMPURITY]
Common Name English
EMBAY 8440
Code English
PRAZIQUANTEL (EMA EPAR: VETERINARY)
Common Name English
PRAZIQUANTEL [EP MONOGRAPH]
Common Name English
PRAZIQUANTEL [WHO-IP]
Common Name English
CYSTICIDE
Brand Name English
PRAZIQUANTEL [JAN]
Common Name English
PRAZIQUANTEL [GREEN BOOK]
Common Name English
2-(Cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Common Name English
PRAZIQUANTEL [USAN]
Common Name English
PRAZIQUANTEL [USP MONOGRAPH]
Common Name English
4H-PYRAZINO(2,1-A)ISOQUINOLIN-4-ONE, 2-(CYCLOHEXYLCARBONYL)-1,2,3,6,7,11B-HEXAHYDRO-
Common Name English
NSC-757285
Code English
PRAZIQUANTELUM [WHO-IP LATIN]
Common Name English
praziquantel [INN]
Common Name English
Classification Tree Code System Code
EMA VETERINARY ASSESSMENT REPORTS PROFENDER [AUTHORIZED]
Created by admin on Mon Mar 31 19:00:58 GMT 2025 , Edited by admin on Mon Mar 31 19:00:58 GMT 2025
CFR 21 CFR 520.1872
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CFR 21 CFR 520.1870
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WHO-ESSENTIAL MEDICINES LIST 6.1.3
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EMA VETERINARY ASSESSMENT REPORTS BROADLINE(AUTHORIZED)
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CFR 21 CFR 520.1200
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CFR 21 CFR 520.1871
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CFR 21 CFR 522.1870
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WHO-VATC QP52AA01
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CFR 21 CFR 520.1199
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WHO-VATC QP52AA51
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LIVERTOX NBK548916
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CFR 21 CFR 520.903D
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CFR 21 CFR 520.1453
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WHO-ESSENTIAL MEDICINES LIST 6.1.1
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CFR 21 CFR 520.1445
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NDF-RT N0000175481
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EMA VETERINARY ASSESSMENT REPORTS PROFENDER [AUTHORIZED]
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CFR 21 CFR 520.1447
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WHO-ATC P02BA01
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NCI_THESAURUS C250
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CFR 21 CFR 520.1198
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FDA ORPHAN DRUG 19487
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CFR 21 CFR 524.775
Created by admin on Mon Mar 31 19:00:58 GMT 2025 , Edited by admin on Mon Mar 31 19:00:58 GMT 2025
Code System Code Type Description
NSC
757285
Created by admin on Mon Mar 31 19:00:58 GMT 2025 , Edited by admin on Mon Mar 31 19:00:58 GMT 2025
PRIMARY
MESH
D011223
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PRIMARY
RS_ITEM_NUM
1554603
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PRIMARY
SMS_ID
100000081420
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PRIMARY
ChEMBL
CHEMBL976
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PRIMARY
LACTMED
Praziquantel
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PRIMARY
ECHA (EC/EINECS)
259-559-6
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PRIMARY
EVMPD
SUB10008MIG
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PRIMARY
DRUG BANK
DB01058
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PRIMARY
PUBCHEM
4891
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PRIMARY
CAS
55268-74-1
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PRIMARY
WIKIPEDIA
PRAZIQUANTEL
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PRIMARY
FDA UNII
6490C9U457
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PRAZIQUANTEL
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PRIMARY Description: A white or almost white, crystalline powder; odourless or with a faint characteristic odour. Solubility: Very slightly soluble in water; freely soluble in ethanol (~750 g/l) TS. Category: Antischistosomal drug. Storage: Praziquantel should be kept in a well-closed container, protected from light. Definition: Praziquantel contains not less than 98.5% and not more than 101.0% of C19H24N2O2, calculated with reference to thedried substance.
MERCK INDEX
m9107
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PRIMARY Merck Index
DRUG CENTRAL
2241
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PRIMARY
DAILYMED
6490C9U457
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PRIMARY
RXCUI
8628
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PRIMARY RxNorm
INN
3895
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PRIMARY
NCI_THESAURUS
C47683
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PRIMARY
EPA CompTox
DTXSID9021182
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PRIMARY