Praziquantel

HCID 4891CAS 55268-74-1

기본 정보

표준 SMILES
O=C(C1CCCCC1)N1CC(=O)N2CCc3ccccc3C2C1
InChIKey
FSVJFNAIGNNGKK-UHFFFAOYSA-N
분자식
C19H24N2O2
평균 분자량
312.4 g/mol
단동위원소 질량
312.18377801

개요

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

이름 및 식별자

우선 이름
Praziquantel
IUPAC
2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
영어명
Praziquantel
분자식
C19H24N2O2
분자량
312.41

이름 및 동의어

praziquantel55268-74-1BiltricideDroncitEmbay 8440PraziquantelumCysticideDTXSID90211822-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-oneprazicuantelEMBAY-8440Praziquantel Tablets
이름 더 보기
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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
2.7
극성 표면적
40.6 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
23

실험 및 물리화학적 성질

DrugsPharmaceuticals
LogP · 2건

2.5

2.43

Solubility · 2건

3.81e-01 g/L

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

Human Drugs · 4건

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 · 4건

EMA approved medicines: Veterinary medicine

Active Ingredients (Praziquantel) -> FDA Greenbook

Pharmaceuticals -> UK Veterinary Medicines Directorate List

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Melting Point · 2건

136-138 °C

136 °C

물리화학적 성질

녹는점
136 · 136-138 C
끓는 점
1377 ℃ · 1377℃
밀도
1.1209 · 1.1209 (rough estimate)
굴절률
1.56 · 1.5600 (estimate)
인화점
110 ° · >110°(230°F)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C

화학적 성질

White Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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%)

독성 정보

Hepatotoxicity · 1건

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 · 1건

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 · 6건

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

안전 데이터

wgk
1
rtecs
UQ4150000
독성
LD50 in mice, rats (mg/kg): 2000-3000 orally; >3000 s.c. (Muermann)
HS 번호
29339900
risk_code
11-34
hazard_code
F,C

화학 및 산업

약리 정보

ATC Code · 3건

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

P02BA01

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

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 · 1건

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.

용도 및 제조

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

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

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

응용 분야

개요Praziquantel (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.

용도Praziquantel 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.

공급사50 곳

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]

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2건

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