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
Show more names
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
- Formal charge
- 0
- Complexity
- 472
Experimental & physicochemical properties
LogP
2.5
2.43
Solubility
3.81e-01 g/L
>46.9 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
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
EMA approved medicines: Veterinary medicine
Active Ingredients (Praziquantel) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point
136-138 °C
136 °C
Collision Cross Section
178.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9021182]
162.35 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
176.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
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
- solubility
- 5 mg/mL · ethanol: soluble5mg/mL
- form
- powder or crystals
- pka
- -0.98 · -0.98±0.20(Predicted)
- color
- Crystals from EtOAc/hexane
- Water Solubility
- Freely soluble in ethanol or dichloromethane. Slightly soluble in water
- Merck
- 13 · 13,7802
- BRN
- 761557 · 761557
- BCS Class
- 2 · 2
- Major Application
- clinical testing
- 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
- InChIKey
- FSVJFNAIGNNGKK-UHFFFAOYSA-N
- SMILES
- O=C1CN(CC2N1CCc3ccccc23)C(=O)C4CCCCC4
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6490 C9U457 · 6490C9U457
- ATC code
- 2 BA01 · P02BA01
- EPA Substance Registry System
- Praziquantel (55268-74-1)
- UNSPSC Code
- 51452701 · 51452701
- NACRES
- 85 · NA.85
- Protein binding
- 80 % · 80%
- Excreted unchanged in urine
- 80 % · 80% as metabolites
- Biological half-life
- 1 · 1-1.5 (metabolites 4 hours) / Slightly increased
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 412 · H412
- Precautionary statements
- 273 · P273
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- F,C
- Risk Statements
- 11 · 11-34
- Safety Statements
- 16 · 16-26-36/37/39-45-24/25
- WGK Germany
- 1 · 1
- RTECS
- 4150000 · UQ4150000
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 3 · Aquatic Chronic 3
- Toxicity
- 50 in · LD50 in mice, rats (mg/kg): 2000-3000 orally; >3000 s.c. (Muermann)
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Hepatotoxicity
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
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
Drug Induced Liver Injury Rank (DILIrank 2.0)
Praziquantel
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- F,C
- safety_code
- 16-26-36/37/39-45-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H412
- Hazard Classifications
- Aquatic Chronic 3
- Precautionary statements
- P273
Chemistry & industry
Pharmacology
ATC Code
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
P02BA01
Pharmacodynamics
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
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.
FDA Pharmacological Classification
6490C9U457
PRAZIQUANTEL
Established Pharmacologic Class [EPC] - Anthelmintic
Praziquantel is an Anthelmintic.
PRAZIQUANTEL
Anthelmintic [EPC]
Absorption, Distribution and Excretion
After oral administration of praziquantel, about 80% of the dose is absorbed. In subjects with normal hepatic function who received 40 mg/kg of praziquantel under fasting conditions, the mean ± SD Cmax and AUC were 0.83 ± 0.52 µg/mL and 3.02 ± 0.59 µg/mL x hr. The Tmax was 1.48 ± 0.74 hours.
Approximately 80% of an oral dose of praziquantel is excreted in the kidneys, almost exclusively (greater than 99%) in the form of praziquantel metabolites.
Following a single oral dose of 40 mg/kg of praziquantel in healthy volunteers, the volume of distribution was estimated to be 7695 ± 2716 L.
Following a single oral dose of 40 mg/kg of praziquantel in healthy volunteers, the clearance was estimated to be 11.4 ± 2.8 L/kg/h.
Uses & manufacturing
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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
Linked notes
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