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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 472
실험 및 물리화학적 성질
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]
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
- 용해도
- 5 mg/mL · 에탄올: 용해성5mg/mL
- 물리적 상태
- 분말 또는 결정
- 산도 계수 (pKa)
- -0.98 · -0.98±0.20(Predicted)
- 색상
- 초산 에틸렌/헥산으로부터 얻은 결정입니다
- 수용성
- 에탄올이나 디클로로메탄에 잘 녹습니다. 물에 약간 용해됨
- Merck
- 13 · 13,7802
- BRN
- 761557 · 761557
- BCS Class
- 2 · 2
- 주요 응용
- 임상 시험
- 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
- Praziquantel (55268-74-1)
화학적 성질
White Solid
안전 및 규제
GHS 분류
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.
유해성 정보
독성 정보
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
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
- safety_code
- 16-26-36/37/39-45-24/25
- Hazard Classifications
- Aquatic Chronic 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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.
용도 및 제조
Use Classification
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.
상·하류 제품 정보
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