Pyrantel
Vue d'ensemble
Description
Le pyrantel est un antihelminthique dérivé de la pyrimidine utilisé pour traiter diverses infections parasitaires par des vers, notamment l'ascaridiase, les infections à ankylostomes, l'entérobiase (infection à oxyures), la trichostrongylose et la trichinellose . Il est administré par voie orale et agit en paralysant les vers, qui sont ensuite expulsés de l'organisme par des processus naturels .
Méthodes De Préparation
Voies de synthèse et conditions réactionnelles : Le pyrantel est synthétisé par une série de réactions chimiques impliquant des dérivés de la pyrimidine. La synthèse implique généralement la réaction de la 1-méthyl-2-(2-thiényl)vinyl-5,6-dihydro-4H-pyrimidine avec divers réactifs dans des conditions contrôlées .
Méthodes de production industrielle : La production industrielle du this compound implique souvent l'utilisation de la chromatographie liquide haute performance (HPLC) pour la purification et l'analyse du composé. Le processus comprend l'utilisation d'acétonitrile, d'acide acétique, d'eau et de diéthylamine comme solvants et réactifs .
Analyse Des Réactions Chimiques
Types de réactions : Le pyrantel subit diverses réactions chimiques, notamment des réactions d'oxydation, de réduction et de substitution. Ces réactions sont essentielles pour modifier la structure du composé et améliorer son efficacité .
Réactifs et conditions courants : Les réactifs courants utilisés dans les réactions impliquant le this compound comprennent l'acétonitrile, l'acide acétique, l'eau et la diéthylamine. Les réactions sont généralement effectuées dans des conditions contrôlées de température et de pression afin d'assurer des rendements optimaux .
Principaux produits formés : Les principaux produits formés à partir des réactions impliquant le this compound comprennent son sel de pamoate, qui est utilisé dans diverses formulations pharmaceutiques .
4. Applications de la recherche scientifique
Le this compound a une large gamme d'applications de recherche scientifique, notamment son utilisation en chimie, biologie, médecine et industrie. En médecine, il est utilisé pour traiter les infections parasitaires par des vers chez l'homme et les animaux . En biologie, il est utilisé pour étudier les effets des antihelminthiques sur les vers parasites . En chimie, il est utilisé comme composé modèle pour étudier la synthèse et les réactions des dérivés de la pyrimidine . Dans l'industrie, il est utilisé dans la production de médicaments vétérinaires et d'autres produits pharmaceutiques .
5. Mécanisme d'action
Le this compound agit comme un agent bloquant neuromusculaire dépolarisant, provoquant une contraction soudaine suivie d'une paralysie des helminthes. Cela se traduit par une perte d'adhérence des vers à la paroi intestinale et leur expulsion de l'organisme . Le composé cible les récepteurs cholinergiques nicotiniques des vers, ce qui entraîne une dépolarisation persistante et une paralysie spastique .
Composés similaires :
- Mébendazole
- Albendazole
Comparaison : Le this compound est unique par son mécanisme d'action en tant qu'agent bloquant neuromusculaire dépolarisant, tandis que le mébendazole et l'albendazole agissent en inhibant la polymérisation de la tubuline dans les vers . Le this compound est également connu pour son action rapide et son efficacité après une seule dose, ce qui en fait un choix privilégié pour le traitement des infections parasitaires par des vers .
Applications De Recherche Scientifique
Pyrantel has a wide range of scientific research applications, including its use in chemistry, biology, medicine, and industry. In medicine, it is used to treat parasitic worm infections in humans and animals . In biology, it is used to study the effects of anthelmintic agents on parasitic worms . In chemistry, it is used as a model compound for studying the synthesis and reactions of pyrimidine derivatives . In industry, it is used in the production of veterinary medicines and other pharmaceutical products .
Mécanisme D'action
Pyrantel acts as a depolarizing neuromuscular blocking agent, causing sudden contraction followed by paralysis of the helminths. This results in the worms losing their grip on the intestinal wall and being expelled from the body . The compound targets nicotinic cholinergic receptors in the worms, leading to persistent depolarization and spastic paralysis .
Comparaison Avec Des Composés Similaires
- Mebendazole
- Albendazole
Comparison: Pyrantel is unique in its mechanism of action as a depolarizing neuromuscular blocking agent, whereas mebendazole and albendazole work by inhibiting the polymerization of tubulin in the worms . This compound is also known for its rapid action and effectiveness after a single dose, making it a preferred choice for treating parasitic worm infections .
Propriétés
IUPAC Name |
1-methyl-2-[(E)-2-thiophen-2-ylethenyl]-5,6-dihydro-4H-pyrimidine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C11H14N2S/c1-13-8-3-7-12-11(13)6-5-10-4-2-9-14-10/h2,4-6,9H,3,7-8H2,1H3/b6-5+ |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
YSAUAVHXTIETRK-AATRIKPKSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CN1CCCN=C1C=CC2=CC=CS2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CN1CCCN=C1/C=C/C2=CC=CS2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C11H14N2S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID5023538 |
Source
|
| Record name | Pyrantel | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5023538 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
206.31 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Solubility |
insoluble in water, TASTELESS; PRACTICALLY INSOL IN ALCOHOL OR WATER /PAMOATE/, Tastelss, yellow crystalline powder. Insol in water. /Pamoate/, Insoluble in water, slightly soluble in dimethylformamide, and soluble in dimethyl sulfoxide. |
Source
|
| Record name | Pyrantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB11156 | |
| 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 | PYRANTEL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3252 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Mechanism of Action |
By promoting the release of acetylcholine, inhibiting cholinesterase, and stimulating ganglionic neurons, pyrantel serves as a depolarizing neuromuscular blocking agent in helminths. This causes extensive depolarization of the helminth muscle membrane, resulting in tension to the helminth's muscles, leading to paralysis and release of their attachment to the host organism intestinal walls. This action is unlike piperazine, which is a hyperpolarizing neuromuscular blocking agent that causes relaxation of the helminth muscles, leading to a subsequent detachment from the intestinal wall. Excretion of the parasites in the feces occurs by normal peristalsis., PYRANTEL & ITS ANALOGS ARE DEPOLARIZING NEUROMUSCULAR BLOCKING AGENTS. THEY INDUCE MARKED, PERSISTENT ACTIVATION OF NICOTINIC RECEPTORS, WHICH RESULTS IN SPASTIC PARALYSIS OF THE WORM. PYRANTEL ALSO INHIBITS CHOLINESTERASES. /PYRANTEL PAMOATE AND ANALOGS/, PYRANTEL ... CAUSES A SLOWLY DEVELOPING CONTRACTURE OF PREPARATIONS OF ASCARIS AT 1% OF THE CONCENTRATION OF ACETYLCHOLINE REQUIRED TO PRODUCE THE SAME EFFECT. IN SINGLE MUSCLE CELLS OF THIS HELMINTH, PYRANTEL CAUSES DEPOLARIZATION & INCREASED SPIKE-DISCHARGE FREQUENCY, ACCOMPANIED BY INCREASE IN TENSION. |
Source
|
| Record name | Pyrantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB11156 | |
| 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 | PYRANTEL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3252 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Crystals from methanol, Yellow, crystalline solid | |
CAS No. |
15686-83-6 |
Source
|
| Record name | Pyrantel | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=15686-83-6 | |
| 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 | Pyrantel [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0015686836 | |
| 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 | Pyrantel | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB11156 | |
| 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 | Pyrantel | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID5023538 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Pyrantel | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.036.143 | |
| 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 | PYRANTEL | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/4QIH0N49E7 | |
| 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 | PYRANTEL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3252 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Melting Point |
178-179 °C, White crystals from hot methanol; max absorption (water): 312 nm (log e= 4.27); MP: 148-150 °C /Tartrate/ |
Source
|
| Record name | PYRANTEL | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3252 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
![(2E,4E)-5-[(1S,7S,8S,9R)-7-acetyloxy-4-methoxycarbonyl-9-methyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid](/img/structure/B1679821.png)
