2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

• ChemBase编号: 929
• 分子式: C19H24N2O2
• 平均质量: 312.40606
• 单一同位素质量: 312.18377802
• SMILES: O=C(N1CC2N(CCc3c2cccc3)C(=O)C1)C1CCCCC1
• Canonical SMILES: O=C(N1CC(=O)N2C(C1)c1ccccc1CC2)C1CCCCC1
• InChI: 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

名称和登记号

名称

• IUPAC标准名: 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
• IUPAC传统名: praziquantel; 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one
• 商标名: Biltricide
• 别名: 2-(环己基羰基)-1,2,3,6,7-11b-六氢-4H-吡嗪并(2,1a)异喹啉-4-酮; 吡喹酮; 2-(Cyclohexylcarbonyl)-1,2,3,6,7-11b-hexahydro-4H-pyrazino[2,1-aisoquinolin-4-one; Praziquantel; Biltricide; Droncit; Biliricide; Cesol; 2-Cyclohexylcarbonyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino(2,1-a) isoquinolin-4-one; Praziquantel; 2-(Cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one; (+/-)-Praziquantel; Azinox; Cysticide; Distocide; Embay 8440; Prazinon; Pyquiton; Warmnil; 2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

登记号

• CAS号: 55268-74-1
• EC号: 259-559-6
• MDL号: MFCD00058531
• Beilstein号: 761557
• PubChem SID: 24278635; 46507082; 24870350; 160964392
• PubChem CID: 4891

理论计算性质

JChem

• Acid pKa: 19.378233
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 2.3015618
• LogD (pH = 7.4): 2.3015625
• Log P: 2.3015625
• 摩尔折射率: 88.7851 cm^3
• 极化性: 34.49192 Å^3
• 极化表面积: 40.62 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.42
• LOG S: -2.91
• 溶解度: 3.81e-01 g/l

分子性质

理化性质

• 溶解度: 400 mg/L; Chloroform; Methanol
• 外观: White Solid
• 熔点: 134-136°C; 136-141°C
• 疏水性(logP): 2.5; 3.36

安全信息

• 保存条件: 0°C; -20°C; -20°C Freezer
• RTECS编号: UQ4150000
• 德国WGK号: 1
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C; 2-8°C

药理学性质

• 生物活性机理: Causes in susceptible worms: loss of intracellular calcium; disintegration of the schistosome tegument.; vacuolization; musculature paralysis; massive contractions; Membrane permeabilizer

产品相关信息

• 纯度: 95%; 98.5%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Anthelmintic
• Empirical Formula (Hill Notation): C19H24N2O2

详细说明

MP Biomedicals - 02156346

Purity: 98.5%

DrugBank - DB01058

• Drug Groups: approved
• Description: An anthelmintic used in most schistosome and many cestode infestations. [PubChem]
• Indication: For the treatment of infections due to all species of schistosoma.
• Pharmacology: Praziquantel is an anthelmintic used in most schistosome and many cestode infestations. Praziquantel effects the permeability of the cell membrane resulting in the contraction of schistosomes. 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 calcium 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 limited very specifically to trematodes and cestodes; nematodes (including filariae) are not affected.
• Biotransformation: renal
• Absorption: Rapidly absorbed (80%)
• Half Life: 0.8-1.5 hours (in serum)
• Protein Binding: 80 to 85%
• References: Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. [Pubmed] ; McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1691

Research Area: Infection
Biological Activity:
Praziquantel(Biltricide, Droncit) is an anthelmintic effective against flatworms. It increases the permeability of the membranes of schistosome cells towards calcium ions. The drug， thereby induces contraction of the parasites, resulting in paralysis in the contracted state. The dying parasites are dislodged from their site of action in the host organism and may enter systemic circulation or may be destroyed by host immune reaction (phagocytosis). Additional mechanisms including focal disintegrations and disturbances of oviposition (laying of eggs) are seen in other types of sensitive parasites. [1]

Sigma Aldrich - P4668

Application
Praziquantel is a potent anthelmintic used in against schistosome and many cestode infestations. It is used to study voltage-gated Ca2+ channels and is a potential small molecule neurogenic1.
Biochem/physiol Actions
Praziquantel increases the permeability of the tegmentum to Ca2+ which results in the contraction of schistosomes and death. Praziquantel causes vacuolization and disintegration of the schistosome tegument. It is more effective on adult worms than young worms. It inhibits glucose uptake, which lowers glycogen levels and stimulates lactate release

Sigma Aldrich - 46648

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - P702095

Anthelmintic, effective against flatworms.

参考文献

• Doenhoff MJ, Cioli D, Utzinger J: Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis. Curr Opin Infect Dis. 2008 Dec;21(6):659-67. Pubmed
• McManus DP, Loukas A: Current status of vaccines for schistosomiasis. Clin Microbiol Rev. 2008 Jan;21(1):225-42. Pubmed
• http://en.wikipedia.org/wiki/Praziquantel
• Kuhn, I., et al.: Bioorg. Med. Chem., 18, 7900 (2010)
• Wang, W., et al.: Parasitol., 137, 1905 (2010)