HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Praziquantel
biltricide · Drontal · Praziguantel · Praziquentel · 2-(cyclohexanecarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one · Cesol · Azinox · droncit
Identifikatoren & physikalische Daten
| CAS No. | 55268-74-1 |
|---|---|
| Summenformel | C19H24N2O2 |
| Durchschnittliche Molmasse | 312,4 g/mol |
| Monoisotopische Masse | 312,18377801 g/mol |
| SMILES | O=C(C1CCCCC1)N1CC(=O)N2CCc3ccccc3C2C1 |
| InChIKey | FSVJFNAIGNNGKK-UHFFFAOYSA-N |
| PubChem CID | 4891 |
| ChEMBL | CHEMBL976 |
| ChEBI | CHEBI:91583 |
| EC No. | 259-559-6 |
| DTXSID | DTXSID9021182 |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 23 |
| Formalladung | 0 |
| Komplexität | 472 |
| Arzneimittel | Pharmaceuticals |
| LogP (Verteilungskoeffizient) | 2.52.43 |
| Löslichkeit | 3.81e-01 g/L>46.9 [ug/mL] (The mean of the results at pH 7.4)ethanol: soluble5mg/mLFreely soluble in ethanol or dichloromethane. Slightly soluble in water |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAnthelminticsAntiparasitic AgentsFDA approved drugs -> Active ingredientAntischistosomals and other antitrematode medicines |
| Animal Drugs | EMA approved medicines: Veterinary medicineActive Ingredients (Praziquantel) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Schmelzpunkt | 136-138 °C136 °C136-138 C |
| Physical Description | Solid |
| Collision Cross Section | 178.5 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID9021182]162.35 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]176.5 Ų [M+H]+ [CCS Type: TW |
| Siedepunkt | 1377℃ |
| Dichte | 1.1209 (rough estimate) |
| Brechungsindex | 1.5600 (estimate) |
| Flammpunkt | >110°(230°F) |
| Lagerbedingungen | Sealed in dry,Store in freezer, under -20°C |
| Aggregatzustand | powder or crystals |
| pKa (Säurekonstante) | -0.98±0.20(Predicted) |
| Farbe | Crystals from EtOAc/hexane |
| Merck | 13,7802 |
| BRN | 761557 |
| BCS Class | 2 |
| Hauptanwendungen | 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 |
| EPA chemische Informationen | Praziquantel (55268-74-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | Praziquantel: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP 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 Categories | Aquatic Chronic 3 (91.2%) |
| 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. |
| Toxizitätsübersicht | Praziquantel is the drug of choice for the treatment of all forms of schistosomiasis. It has low toxicity and mild side effectshowever, 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)PraziquantelAmbiguous-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 1 |
| Zollcode | 29339900 |
| RTECS-Nr. | UQ4150000 |
| R-Sätze (R) | 11-34 |
| Toxizität | LD50 in mice, rats (mg/kg): 2000-3000 orally>3000 s.c. (Muermann) |
| Gefahrensymbole | F,C |
| Sicherheitshinweise (S) | 16-26-36/37/39-45-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Aquatic Chronic 3 |
Anwendungen & Verwendung
Beschreibung
Praziquantel (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.
Verwenden
Praziquantel 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.