Praziquantel

HCID 4891CAS 55268-74-1

Basic information

Standard SMILES
O=C(C1CCCCC1)N1CC(=O)N2CCc3ccccc3C2C1
InChIKey
FSVJFNAIGNNGKK-UHFFFAOYSA-N
Molecular formula
C19H24N2O2
Average molar mass
312.4 g/mol
Monoisotopic mass
312.18377801

Overview

2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one is a member of isoquinolines.

Names & identifiers

Preferred name
Praziquantel
IUPAC
2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
English name
Praziquantel
Molecular formula
C19H24N2O2
Molecular weight
312.41

Names & synonyms

praziquantel55268-74-1BiltricideDroncitEmbay 8440PraziquantelumCysticideDTXSID90211822-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-oneprazicuantelEMBAY-8440Praziquantel Tablets
Show more names
DrontalPraziguantelPraziquentel2-(cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-oneCesolAzinoxWarMnilpyquiton
NSC-757285DTXCID501182Praziquantel Injection4H-Pyrazino(2,1-a)isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-2-(Cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino(2,1-a)isoquinolin-4-onePrasiquantel6490C9U4572-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

Database identifiers

CAS
55268-74-1
PubChem CID
4891
DTXSID
DTXSID9021182
ChEMBL
CHEMBL976
ChEBI
CHEBI:91583
UNII
6490C9U457
EC Number
259-559-6
Nikkaji
J2.787A、J457.026J

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
40.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
23

Experimental & physicochemical properties

DrugsPharmaceuticals
LogP · 2 items

2.5

2.43

Solubility · 2 items

3.81e-01 g/L

>46.9 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Anthelmintics; Antiparasitic Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Antischistosomals and other antitrematode medicines

Animal Drugs · 4 items

EMA approved medicines: Veterinary medicine

Active Ingredients (Praziquantel) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Melting Point · 2 items

136-138 °C

136 °C

Physicochemical properties

Melting point
136 · 136-138 C
Boiling point
1377 ℃ · 1377℃
Density
1.1209 · 1.1209 (rough estimate)
refractive index
1.56 · 1.5600 (estimate)
Flash point
110 ° · >110°(230°F)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C

Safety & regulation

GHS classification

GHS Classification · 4 items

This chemical does not meet GHS hazard criteria for 1.8% (2 of 113) of reports.

H412 (91.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 113 reports by companies from 7 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationPraziquantel: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-: Environment tier I assessment
Hazard Classes and CategoriesAquatic Chronic 3 (91.2%)

Toxicology

Hepatotoxicity · 1 item

Praziquantel therapy has been associated with elevations in serum aminotransferase levels in up to 27% of patients, but these abnormalities were self-limiting. Praziquantel has been rarely associated with clinically apparent liver injury, which generally accompanied hypersensitivity reactions such as rash and fever. In a large retrospective survey from China, 2 of 25,000 treated patients were reported to have developed jaundice after praziquantel therapy, but no specific information about the two cases was provided. There have been few studies of long term therapy with praziquantel, and most controlled trials of this agent have used one day courses without serum aminotransferase monitoring. However, millions of people have been treated with praziquantel as a part of large scale control strategies in China where schistosomiasis Japonica is endemic. The combination of praziquantel preventive therapy and snail control has resulted in marked decreases in the prevalence of infection in the population with no evidence of significant toxicity. Thus, mild acute liver injury can accompany systemic hypersensitivity reactions to praziquantel, but both the allergic reaction and the liver injury tend to be short-lived and resolve rapidly even without specific therapy.

Toxicity Summary · 1 item

Praziquantel is the drug of choice for the treatment of all forms of schistosomiasis. It has low toxicity and mild side effects; however, a major weakness is its relative inefficacy against recent infections, and this might occasionally result in low cure rates in hyperendemic areas.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Praziquantel

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
1
rtecs
UQ4150000
hs_code
29339900
Toxicity
LD50 in mice, rats (mg/kg): 2000-3000 orally; >3000 s.c. (Muermann)
risk_code
11-34

Chemistry & industry

Pharmacology

ATC Code · 3 items

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

P02BA01

Protein BindingApproximately 80% of praziquantel is bound exclusively to albumin.
Pharmacodynamics · 1 item

In vitro studies on trematodes and cestodes have shown that praziquantel induces a rapid contraction of schistosomas by a specific effect on the permeability of the cell membrane. 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 Ca2<sup>+</sup>-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 specific to trematodes and cestodes; nematodes (including filariae) are not affected. Praziquantel is active against schistosoma (for example, Schistosoma mekongi, Schistosoma japonicum, Schistosoma mansoni and Schistosoma hematobium), and infections due to the liver flukes, Clonorchis sinensis/Opisthorchis viverrini. Published in vitro data have shown a potential lack of efficacy of praziquantel against migrating schistosomulae. 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.

Mechanism of Action · 1 item

Although the exact mechanism of action is unknown, praziquantel was hypothesized to target the β subunits of voltage-gated Ca<sub>2+</sub> channels, particularly in Schistosoma mansoni and Schistosoma japonicum, due to the lack of two conserved serine residues in these subunits. This is supported by the finding that co-administration of calcium channel blockers like nicarpidine and nifedipine renders 50% of Schistosoma mansoni resistant to praziquantel. Increased exposure of antigens on the worm surface was also observed, but little research has been done to elucidate on the mechanism of action.

Biological Half-LifeFollowing oral administration, the elimination half-life of praziquantel in serum ranges between 0.8 to 1.5 hours.
Metabolism/MetabolitesPraziquantel is rapidly metabolized by the cytochrome P450 enzyme system and undergoes a first-pass effect after oral administration.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >10
Household ProductsInformation on 2 consumer products that contain Praziquantel in the following categories is provided:
Use Classification · 2 items

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Applications · 5 items

UsesIt is a kind of broad-spectrum anti-parasitic disease drug. It can be used for the treatment and prevention of schistosomiasis, cysticercosis, paragonimiasis, hydatid disease, fasciolopsiasis, hydatid disease, and worm infection. It can also be used as anthelmintic and is effective in treating animal gastrointestinal nematodes. It can be mixed in the feed for application. The product is a kind of anthelmintic drug effective in treating Schistosoma japonicum, Schistosoma mansoni and Schistosoma haematobium, Clonorchis sinensis, Paragonimus westermani, fasciolopsis buski, tapeworms and cysticercosis. It has a especially strong killing effect on tapeworm and is currently of highest efficiency among anti-schistosomiasis drug. It is a kind of anthelmintics drug mainly used for treating schistosomiasis. It can also used for treating Fahrenheit schistosomiasis, taeniasis, paragonimiasis, and cysticercosis

DescriptionPraziquantel (PZQ) is an isoquinoline derivative with most of the biological activity found in the levo enantiomer. The compound has no activity against nematodes, but it is highly effective against cestodes and trematodes.

UsesPraziquantel is a potent anthelmintic used against schistosome and many cestode infestations. It is used to study voltage-gated Ca2+ channels and is a potential small molecule neurogenic.

Usesanthelmintic; EMBAY-8440

UsesAnthelmintic, effective against flatworms.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北研科时代科技有限公司15780669880 · [email protected]

Additional notes

DefinitionChEBI: 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one is a member of isoquinolines.

Related reactions

2 records

Linked notes

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