molecular formula C11H14N2S B1679900 Pyrantel CAS No. 15686-83-6

Pyrantel

Cat. No.: B1679900
CAS No.: 15686-83-6
M. Wt: 206.31 g/mol
InChI Key: YSAUAVHXTIETRK-AATRIKPKSA-N
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Preparation Methods

Synthetic Routes and Reaction Conditions: Pyrantel is synthesized through a series of chemical reactions involving pyrimidine derivatives. The synthesis typically involves the reaction of 1-methyl-2-(2-thienyl)vinyl-5,6-dihydro-4H-pyrimidine with various reagents under controlled conditions .

Industrial Production Methods: Industrial production of this compound often involves the use of high-performance liquid chromatography (HPLC) for the purification and analysis of the compound. The process includes the use of acetonitrile, acetic acid, water, and diethylamine as solvents and reagents .

Chemical Reactions Analysis

Types of Reactions: Pyrantel undergoes various chemical reactions, including oxidation, reduction, and substitution reactions. These reactions are essential for modifying the compound’s structure and enhancing its efficacy .

Common Reagents and Conditions: Common reagents used in the reactions involving this compound include acetonitrile, acetic acid, water, and diethylamine. The reactions are typically carried out under controlled temperature and pressure conditions to ensure optimal yields .

Major Products Formed: The major products formed from the reactions involving this compound include its pamoate salt, which is used in various pharmaceutical formulations .

Mechanism of Action

Properties

IUPAC Name

1-methyl-2-[(E)-2-thiophen-2-ylethenyl]-5,6-dihydro-4H-pyrimidine
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 PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

YSAUAVHXTIETRK-AATRIKPKSA-N
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 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 PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C11H14N2S
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

DSSTOX Substance ID

DTXSID5023538
Record name Pyrantel
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Molecular Weight

206.31 g/mol
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.
Record name Pyrantel
Source DrugBank
URL https://www.drugbank.ca/drugs/DB11156
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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.
Record name Pyrantel
Source DrugBank
URL https://www.drugbank.ca/drugs/DB11156
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Record name PYRANTEL
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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
Record name Pyrantel
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Record name Pyrantel [INN:BAN]
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Record name Pyrantel
Source DrugBank
URL https://www.drugbank.ca/drugs/DB11156
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Record name Pyrantel
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Record name PYRANTEL
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Record name PYRANTEL
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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/
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

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