Pyrantel
准备方法
合成路线和反应条件： 吡喃酯通过一系列涉及嘧啶衍生物的化学反应合成。 合成通常涉及在受控条件下将 1-甲基-2-(2-噻吩基)乙烯基-5,6-二氢-4H-嘧啶与各种试剂反应 .
工业生产方法： 吡喃酯的工业生产通常涉及使用高效液相色谱 (HPLC) 来纯化和分析化合物。 该过程包括使用乙腈、乙酸、水和二乙胺作为溶剂和试剂 .
化学反应分析
反应类型： 吡喃酯经历各种化学反应，包括氧化、还原和取代反应。 这些反应对于改变化合物的结构和增强其功效至关重要 .
常用试剂和条件： 涉及吡喃酯的反应中使用的常用试剂包括乙腈、乙酸、水和二乙胺。 反应通常在受控的温度和压力条件下进行，以确保最佳产量 .
形成的主要产物： 涉及吡喃酯的反应形成的主要产物包括其扑酸盐，该盐用于各种药物制剂 .
科学研究应用
Clinical Applications
Pyrantel is primarily indicated for the treatment of:
- Ascariasis : Caused by Ascaris lumbricoides.
- Enterobiasis : Commonly known as pinworm infection caused by Enterobius vermicularis.
- Hookworm Infections : Particularly effective against Ancylostoma duodenale and Necator americanus.
The standard dosage for these infections is typically around 10 mg/kg for ascariasis and enterobiasis, while a 3-day treatment at the same daily dose is recommended for hookworms .
Efficacy Against Soil-Transmitted Helminths
Recent studies have demonstrated that this compound pamoate significantly reduces worm burden in cases of soil-transmitted helminths. For instance, a study showed a reduction in worm burden by 53-72% when administered post-exposure .
Post-Exposure Prophylaxis
This compound pamoate has been evaluated for its use as a post-exposure prophylactic treatment. Administering it immediately after potential exposure to larval infections can paralyze the larvae in the gastrointestinal tract, preventing them from entering systemic circulation .
Case Study 1: Efficacy in Pediatric Populations
A randomized controlled trial involving children in sub-Saharan Africa demonstrated that this compound was highly effective in treating ascariasis and enterobiasis, achieving cure rates exceeding 96% . The study highlighted its safety profile and minimal side effects, making it suitable for mass drug administration programs.
Case Study 2: Use in Veterinary Medicine
In veterinary applications, this compound tartrate has shown effectiveness against various parasitic infections in animals. Its hydrophilic nature allows systemic absorption, which is beneficial for treating infections that have entered circulation . However, this form is associated with higher toxicity risks in humans.
Conclusions
This compound remains a cornerstone in the treatment of intestinal helminth infections due to its efficacy and safety profile. Its unique mechanism of action allows it to effectively paralyze and expel parasites from the host's gastrointestinal tract. Ongoing research continues to explore its potential applications, particularly in preventive measures against parasitic infections.
作用机制
吡喃酯作为一种去极化神经肌肉阻断剂发挥作用，导致蠕虫突然收缩，然后麻痹。 这会导致蠕虫失去对肠壁的抓握，并从体内排出 . 该化合物靶向蠕虫中的烟碱型胆碱能受体，导致持续去极化和痉挛性麻痹 .
类似化合物：
- 甲苯达唑
- 阿苯达唑
比较： 吡喃酯的去极化神经肌肉阻断剂作用机制是独一无二的，而甲苯达唑和阿苯达唑则通过抑制蠕虫中微管蛋白的聚合起作用 . 吡喃酯还以其单剂量快速作用和有效性而闻名，使其成为治疗寄生虫感染的首选 .
相似化合物的比较
- 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 .
生物活性
Pyrantel is a broad-spectrum anthelmintic agent primarily used for the treatment of various parasitic worm infections. Its biological activity is characterized by a unique mechanism of action, pharmacokinetics, and efficacy across different types of helminths, including nematodes and cestodes. This article synthesizes recent research findings, case studies, and data tables to provide a comprehensive overview of this compound's biological activity.
This compound acts as a depolarizing neuromuscular blocking agent in helminths. It promotes the release of acetylcholine and inhibits cholinesterase, leading to extensive depolarization of the muscle membrane in parasites. This action results in paralysis and detachment from the host's intestinal walls, facilitating the expulsion of the parasites through normal peristalsis . Unlike other anthelmintics such as piperazine, which induce hyperpolarization and relaxation of muscle, this compound's mechanism leads to spastic paralysis .
Pharmacokinetics
- Absorption : this compound is poorly absorbed from the gastrointestinal tract, which allows it to act locally on intestinal parasites. Peak serum concentrations occur 1–3 hours after administration .
- Volume of Distribution : The drug has a limited volume of distribution due to its poor absorption and high local concentration at the site of action.
Case Study: Efficacy Against Pinworms
A study conducted by Kobayashi et al. (2020) evaluated the effectiveness of this compound Pamoate in eliminating pinworms. The study involved administering various concentrations of this compound in a medicated gel diet to Dubia roaches and measuring fecal worm ova counts over time.
Table 1: Fecal Worm Ova Counts Post-Treatment
| Group | This compound Pamoate (mg/g) | Day 1 Total Ova | Day 9 Total Ova | Day 16 Total Ova | Day 23 Total Ova |
|---|---|---|---|---|---|
| A (Control) | 0.0 | 620 | 596 | 444 | 636 |
| B | 3.5 | 509 | 210 | 390 | 160 |
| C | 14.0 | 461 | 553 | 480 | 172 |
| D | 26.0 | 1501 | 160 | 46 | 225 |
| E | 35.0 | 510 | 176 | 358 | 194 |
The results indicated significant reductions in fecal ova counts across all treated groups compared to the control group, with Group D (26 mg/g) showing the most pronounced effects .
Post-Exposure Prophylaxis Study
Another study assessed this compound Pamoate's effectiveness as a post-exposure prophylactic treatment against Angiostrongylus cantonensis. The results showed that treatment significantly reduced worm burden by 53% to 72% when administered shortly after exposure .
Table 2: Worm Recovery Data
| Treatment Group | Mean Worm Recovery (n) |
|---|---|
| Control (No Drug) | |
| Treatment (0-h) | |
| Treatment (2-h) | |
| Treatment (4-h) |
The data indicated a significant difference between control and treatment groups, confirming this compound's efficacy when administered immediately post-infection .
Comparative Efficacy Against Other Helminths
This compound has been shown to be effective against various helminths beyond pinworms:
- Dipylidium caninum : A study demonstrated that this compound-Oxantel induced significant mortality and reduced tegument thickness in D. caninum, confirming its therapeutic potential against tapeworms .
- Caenorhabditis elegans : Early studies reported up to 98% reduction in motility in adult nematodes following treatment with this compound Pamoate, showcasing its broad-spectrum efficacy against nematodes .
属性
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
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
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
体外研究产品的免责声明和信息
请注意，BenchChem 上展示的所有文章和产品信息仅供信息参考。 BenchChem 上可购买的产品专为体外研究设计，这些研究在生物体外进行。体外研究，源自拉丁语 "in glass"，涉及在受控实验室环境中使用细胞或组织进行的实验。重要的是要注意，这些产品没有被归类为药物或药品，他们没有得到 FDA 的批准，用于预防、治疗或治愈任何医疗状况、疾病或疾病。我们必须强调，将这些产品以任何形式引入人类或动物的身体都是法律严格禁止的。遵守这些指南对确保研究和实验的法律和道德标准的符合性至关重要。
