Praziquantel

Base Information Edit

Chemical Name:Praziquantel
CAS No.:55268-74-1
Deprecated CAS:135526-78-2
Molecular Formula:C19H24N2O2
Molecular Weight:312.412
Hs Code.:29339900
European Community (EC) Number:259-559-6,260-741-2
NSC Number:757285
UNII:6490C9U457
DSSTox Substance ID:DTXSID9021182
Nikkaji Number:J457.026J,J2.787A
Wikipedia:Praziquantel
Wikidata:Q424145
NCI Thesaurus Code:C47683
RXCUI:8628
Metabolomics Workbench ID:43296
ChEMBL ID:CHEMBL976
Mol file:55268-74-1.mol

Synonyms:Biltricide;Cesol;Cisticid;Cysticide;Droncit;Drontsit;EMBAY 8440;Prasiquantel;Praziquantel;Praziquantel, (+-)-Isomer;Praziquantel, (R)-Isomer;Praziquantel, (S)-Isomer;Pyquiton;Traziquantel

Suppliers and Price of Praziquantel

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Praziquantel
50g
$ 620.00

TRC
Praziquantel
1g
$ 65.00

TCI Chemical
Praziquantel >98.0%(HPLC)(N)
25g
$ 170.00

TCI Chemical
Praziquantel >98.0%(HPLC)(N)
5g
$ 50.00

Sigma-Aldrich
Praziquantel anthelminic, neurogenic
1g
$ 44.90

Sigma-Aldrich
Praziquantel VETRANAL
250mg
$ 55.20

Sigma-Aldrich
Praziquantel European Pharmacopoeia (EP) Reference Standard
$ 190.00

Sigma-Aldrich
Praziquantel for system suitability European Pharmacopoeia (EP) Reference Standard
$ 190.00

Sigma-Aldrich
Praziquantel for system suitability European Pharmacopoeia (EP) Reference Standard
y0001533
$ 190.00

Sigma-Aldrich
Praziquantel European Pharmacopoeia (EP) Reference Standard
p2670000
$ 190.00

Total 276 raw suppliers

Chemical Property of Praziquantel Edit

Chemical Property:

Appearance/Colour:White or practically white crystalline powder
Melting Point:136-138 °C
Refractive Index:1.5600 (estimate)
Boiling Point:544.1 °C at 760 mmHg
PKA:-0.98±0.20(Predicted)
Flash Point:254.6 °C
PSA：40.62000
Density:1.22 g/cm³
LogP:2.41070
Storage Temp.:−20°C
Solubility.:ethanol: soluble5mg/mL
Water Solubility.:Freely soluble in ethanol or dichloromethane. Slightly soluble in water
XLogP3:2.7
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:312.183778013
Heavy Atom Count:23
Complexity:472

Purity/Quality:

99% ^*data from raw suppliers

Praziquantel ^*data from reagent suppliers

Safty Information:

Pictogram(s): F,C
Hazard Codes:F,C
Statements: 11-34
Safety Statements: 16-26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Drug Classes:Anthelmintic Agents
Canonical SMILES:C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2
Recent ClinicalTrials:Feasibility and Safety of Combining Anti-malarial With Deworming Drugs in African Children
Indications Infections caused by Schistosoma species pathogenic to man (Schistosoma haematobium, S. mansoni, S. japonicum and S. mekongi). The drug is most cost-effective in mixed infections. It is also effective for infections with flukes (Paragonimus westermani and Clonorchis sinensis) and in cestodes (Hymenolepis nana, Diphyllobotrium latum, Taenia saginata, T. solium) including the larval stage of Taenia solium (cysticercosis). Praziquantel has some effect against fascioliasis, but triclabendazole, a new anthelminthic drug still under clinical evaluation is more effective. The neuromuscular effects of praziquantel (Biltricide) appear to increase parasite motility leading to spastic paralysis. The drug increases calcium permeability through parasite-specific ion channels, so that the tegmental and muscle cells of the parasite accumulate calcium.This action is followed by vacuolization and the exposure of hitherto masked tegmental antigens, lipidanchored protein, and actin. Insertion of the drug into the fluke’s lipid bilayer causes conformational changes, rendering the fluke susceptible to antibody- and complement-mediated assault.
Uses It 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 anthelmintic; EMBAY-8440 Anthelmintic, effective against flatworms. 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.
Production method There are a variety of synthetic routes (isoquinoline route, piperazine route, and phenethylamine route). Isoquinoline has advantages such as wide sources of initial raw material and low cost. Isoquinoline can be converted to 1-benzoyl-2-cyano-1,2-dihydro-isoquinoline through Reissetr reaction. It is further converted to 1-benzoyl-aminomethyl-1, 2, 3, 4-tetrahydroisoquinoline through pressurized hydrogenation. Then followed by cyclization with chloroacetyl chloride to give 2-benzoyl-1,3, 4,6,7,11b-hexahydro-2H-pyrazino[2,1-b]isoquinolin-4-ketone. Finally, apply phosphoric acid hydrolysis and perform condensation reaction with cyclohexanecarboxylic acid chloride to obtain the final product. There are a variety of synthetic routes for industrial production including isoquinoline route, piperazine route, and phenethylamine route, among which the isoquinoline route is the best. In this route, first perform adduct reaction between isoquinoline and benzoyl chloride as well as potassium cyanide, further go through catalytic hydrogenation and rearrangement to generate 1-benzoyl-methyl-amino-1,2,3,4-tetrahydroisoquinoline, and then sequentially go through chlorine acetylation, cyclization, hydrolysis under increased pressure, and cyclohexanone acylation to generate the final product. Take phenethylamine as the raw material, after acylation through chloroacetyl chloride, further introduce the amino group after adding terephthalamide potassium for amination reaction, then have cyclization reaction in the action of phosphorus oxychloride to give 3,4-dihydroisoquinoline derivative; further go through hydrogenation and hydrolysis to obtain 1-aminomethyl-tetrahydroquinoline; successively use cyclohexane carboxylic acid chloride and chloroacetyl chloride for acylation and finally go through dehydrochlorination and cyclization to obtain praziquantel. You can alternatively use isoquinoline as raw material; it first go through Reissert reaction to introduce a cyano group in l position and have nitrogen benzoylated, followed by hydrogenation while benzoyl group is transferred to the amino group of the side chain, further introduce a chlorine acetyl group to the amino group on the ring, then successively go through cyclization, hydrolysis, cyclohexanone formylation to obtain praziquantel. The above information is edited by the lookchem of Dai Xiongfeng.
Description 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.
Therapeutic Function Anthelmintic
Clinical Use 2-(Cyclohexylcarbonyl)-1,2,3,6,7, 11b-hexahydro-4Hpyrazino[2,1-a]isoquinolin-4-one (Biltricide) is a broadspectrumagent that is effective against various trematodes (flukes). It has become the agent of choice for the treatmentof infections caused by schistosomes (blood flukes).The drug also provides effective treatment for fasciolopsiasis(intestinal fluke), clonorchiasis (Chinese liver fluke),fascioliasis (sheep liver fluke), opisthorchosis (liver fluke),and paragonimiasis (lung fluke). Praziquantel increases cellmembrane permeability of susceptible worms, resulting inthe loss of extracellular calcium. Massive contractions andultimate paralysis of the fluke musculature occurs, followedby phagocytosis of the parasite.Following oral administration, about 80% of the doseis absorbed. Maximal plasma concentrations are achievedin 1 to 3 hours. The drug is rapidly metabolized in theliver in the first-pass. It is likely that some of the metabolitesare also active. Praziquantel occurs as a white crystallinesolid that is insoluble in water. It is available as600-mg film-coated tablets. The drug is generally welltolerated. Praziquantel is an extremely active broad-spectrum anthelmintic that is well tolerated. It is the most effective of the drugs used in the treatment of schistosomiasis, possessing activity against male and female adults and immature stages. Unlike other agents, it is active against all three major species (S. haematobium, S. mansoni, and S. japonicum). In addition, it has activity against other flukes, such as C. sinensis, Paragonimus westermani, O. viverrini, and the tapeworms (D. latum, H. nana, T. saginata, and T. solium). It is not as effective against F. hepatica. It is used effectively in the treatment of clonorchiasis and paragonimiasis and is an effective alternative agent to niclosamide in the treatment of tapeworm infestations. Schistosomiasis Other trematode infections (except F. hepatica) Tapeworm infection, including cerebral cysticercosis Treatment may need to be prolonged in cerebral cysticercosis.
Drug interactions Potentially hazardous interactions with other drugs Antibacterials: concentration reduced by rifampicin - avoid. Antiepileptics: concentration reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone. Antimalarials: concentration reduced by chloroquine. Ulcer-healing drugs: concentration reduced by cimetidine.

Technology Process of Praziquantel

There total 90 articles about Praziquantel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 87693-75-2
4-(cyclohexylcarbonyl)-6-hydroxy-1-phenethylpiperazine-2-one

: 55268-74-1,135526-78-2,57452-31-0,57452-98-9
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one

Guidance literature:: With hydrogenchloride; at 0 ℃;

Reference yield: 95.0%

: 87693-75-2
4-(cyclohexylcarbonyl)-6-hydroxy-1-phenethylpiperazine-2-one

2-(cyclohexylcarbonyl)-1,3,4,6,7,11b-hexahydro-2H-pyrazino-(2,1-a)-4-isoquinoleinone (PRAZIQUANTEL): 2-(cyclohexylcarbonyl)-1,3,4,6,7,11b-hexahydro-2H-pyrazino-(2,1-a)-4-isoquinoleinone (PRAZIQUANTEL)

: 55268-74-1,135526-78-2,57452-31-0,57452-98-9
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one

Guidance literature:: In 12N-hydrochloric acid;

Reference yield: 93.0%

: 125273-86-1
2-(Cyclohexylcarbonyl)-2,3,6,7-tetrahydro-4H-pyrazino-<2,1-a>-isoquinolin-4-one

: 55268-74-1,135526-78-2,57452-31-0,57452-98-9
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one

Guidance literature:: With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 19h; under 760.051 Torr; Solvent; Inert atmosphere;
DOI:10.1016/j.tet.2017.10.006