Praziquantel
Vue d'ensemble
Description
Le Praziquantel est un médicament largement utilisé pour traiter les infections parasitaires par les vers chez les mammifères, les oiseaux, les amphibiens, les reptiles et les poissons. Chez l'homme, il est spécifiquement utilisé pour traiter la schistosomiase, la clonorchiase, l'opisthorchiase, les infections par les ténias, la cysticercose, l'échinococcose, la paragonimiase, la fasciolopsiase et la fasciolose . C'est un médicament anthelminthique qui agit en affectant la fonction des ventouses du ver . Le this compound a été approuvé pour un usage médical aux États-Unis en 1982 et figure sur la Liste des médicaments essentiels de l'Organisation mondiale de la santé .
Méthodes De Préparation
Le Praziquantel peut être synthétisé par diverses méthodes. Une approche consiste à utiliser la phényléthylamine comme matière de départ. La synthèse implique généralement des étapes telles que l'acylation, l'amination, la cyclisation, l'hydrogénation et l'acylation . Une autre méthode utilise une approche de chimie de flux, qui réduit considérablement le temps de production, passant de jours à minutes, et qui peut être mise à l'échelle pour la production industrielle . Cette méthode implique l'utilisation de phényléthylamine, de chlorure de chloroacétyle et de chlorure de cyclohexanecarbonyle comme réactifs clés .
Analyse Des Réactions Chimiques
Le Praziquantel subit diverses réactions chimiques, notamment :
Oxydation : Cette réaction peut être effectuée à l'aide d'agents oxydants comme le permanganate de potassium.
Réduction : Des réactions d'hydrogénation sont utilisées pour réduire les composés intermédiaires pendant la synthèse.
Cyclisation : Les réactions de cyclisation sont cruciales pour former l'échafaudage de la tétrahydroisoquinoléine.
Les réactifs couramment utilisés dans ces réactions comprennent le chlorure de chloroacétyle, le chlorure de cyclohexanecarbonyle et la phényléthylamine . Les principaux produits formés par ces réactions sont des intermédiaires qui conduisent finalement au composé final du this compound .
4. Applications de la recherche scientifique
Le this compound a une large gamme d'applications de recherche scientifique :
Industrie : Le this compound est produit à l'échelle industrielle pour être utilisé en médecine humaine et vétérinaire.
5. Mécanisme d'action
Le mécanisme d'action exact du this compound n'est pas entièrement compris. Il est considéré qu'il augmente la perméabilité des membranes des cellules de schistosomes aux ions calcium, ce qui entraîne une contraction musculaire et une paralysie des parasites . Cela entraîne le délogement et la mort des parasites. Le this compound cible les sous-unités β des canaux calciques voltage-dépendants, en particulier dans Schistosoma mansoni et Schistosoma haematobium .
Applications De Recherche Scientifique
Praziquantel has a wide range of scientific research applications:
Mécanisme D'action
The exact mechanism of action of praziquantel is not fully understood. it is believed to increase the permeability of the membranes of schistosome cells towards calcium ions, leading to muscle contraction and paralysis of the parasites . This results in the dislodgement and death of the parasites. This compound targets the β subunits of voltage-gated calcium channels, particularly in Schistosoma mansoni and Schistosoma haematobium .
Comparaison Avec Des Composés Similaires
Le Praziquantel est unique par son activité à large spectre contre les trématodes et les cestodes. Parmi les composés similaires, on peut citer :
Albendazole : Utilisé pour traiter une variété d'infections parasitaires par les vers, mais moins efficace contre les schistosomes.
Mebendazole : Un autre anthelminthique à large spectre, mais avec un mécanisme d'action différent.
Oxamniquine : Utilisé spécifiquement pour traiter les infections à Schistosoma mansoni, mais inefficace contre d'autres espèces.
Le this compound se distingue par son efficacité élevée, son faible coût et son activité à large spectre, ce qui en fait un outil essentiel dans la lutte contre les infections parasitaires .
Propriétés
IUPAC Name |
2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
FSVJFNAIGNNGKK-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C19H24N2O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID9021182 |
Source
|
| Record name | Praziquantel | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9021182 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
312.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Praziquantel | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015191 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
>46.9 [ug/mL] (The mean of the results at pH 7.4), 3.81e-01 g/L |
Source
|
| Record name | SID858012 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | Praziquantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01058 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Praziquantel | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015191 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Praziquantel works by causing severe spasms and paralysis of the worms' muscles. This paralysis is accompanied - and probably caused - by a rapid Ca 2+ influx inside the schistosome. Morphological alterations are another early effect of praziquantel. These morphological alterations are accompanied by an increased exposure of schistosome antigens at the parasite surface. The worms are then either completely destroyed in the intestine or passed in the stool. 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. Glutathione S-transferase (GST), an essential detoxification enzyme in parasitic helminths, is a major vaccine target and a drug target against schistosomiasis. Schistosome calcium ion channels are currently the only known target of praziquantel. |
Source
|
| Record name | Praziquantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01058 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
CAS No. |
55268-74-1 |
Source
|
| Record name | Praziquantel | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=55268-74-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Praziquantel [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0055268741 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Praziquantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01058 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | praziquantel | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=757285 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | Praziquantel | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID9021182 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Praziquantel | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.054.126 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | PRAZIQUANTEL | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/6490C9U457 | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | Praziquantel | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015191 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
136 °C |
Source
|
| Record name | Praziquantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01058 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Praziquantel | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015191 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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