PYRANTEL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H14N2S
Molecular Weight	206.307
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CN1CCCN=C1\C=C\C2=CC=CS2

InChI

InChIKey=YSAUAVHXTIETRK-AATRIKPKSA-N

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+

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Description

Pyrantel is an anthelmintic, which acts as an agonist of nicotinic receptors (AChRs) of nematodes and exerts its therapeutic effects by depolarizing their muscle membranes. It is used to treat a number of parasitic worm infections. This includes ascariasis, hookworm infections, enterobiasis (pinworm infection), trichostrongyliasis and trichinellosis. Common adverse reactions include diarrhea, nausea, vomiting, dizziness, headache and somnolence.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic receptors (AChRs) of nematodes 3	Agonist 2,678
Mouse α2βεδ AChRs 3	Agonist 2,678

Conditions

Condition	Modality	Highest Phase	Product
Strongyloidiasis 10	Curative	Approved 8,429	Strongid
Pinworm infection 3	Curative	Approved 8,429	Strongid
Large roundworms infection 3	Curative	Approved 8,429	Strongid
Tapeworm infection 8	Curative	Approved 8,429	Strongid

C_max

Value	Dose	Co-administered	Analyte	Population
0.09 μg/mL	13.3 mg/kg single, oral		PYRANTEL plasma	Equus caballus

AUC

Value	Dose	Co-administered	Analyte	Population
1.06 μg × h/mL	13.3 mg/kg single, oral		PYRANTEL plasma	Equus caballus

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.43 h	13.3 mg/kg single, oral		PYRANTEL plasma	Equus caballus

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349 CYP2C8 693 CYP1A2 1,054 CYP2A6 543 CYP1B1 92 CYP2B6 664 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP4A11 119

Drug as victim

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Target	Modality	Activity
CYP1A2 1,054	substrate 3,367	no
CYP1B1 92	substrate 3,367	no
CYP2A6 543	substrate 3,367	no
CYP2B6 664	substrate 3,367	no
CYP2C19 991	substrate 3,367	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8654	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8654
MolPort	MolPort-002-707-681	https://www.molport.com/shop/molecule-link/MolPort-002-707-681
ZINC	ZINC000000097996	http://zinc15.docking.org/substances/ZINC000000097996

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PubMed

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Title	Date	PubMed
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.	2003 Sep	12920490

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Patents

Sample Use Guides

In Vivo Use Guide

13.2 mg/kg body weight administered one time

Route of Administration: Oral

In Vitro Use Guide

A modified methyl-thiazolyltetrazolium (MTT) reduction assay revealed good in vitro anthelmintic efficacies against Haemonchus contortus infective larvae for pyrantel tartrate at effective dose 0.1 ug/ul – 0.9 ug/ul.

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Name

Type

Language

PYRANTEL

Official Name

English

pyrantel [INN]

Common Name

English

PYRIMIDINE, 1,4,5,6-TETRAHYDRO-1-METHYL-2-(2-(2-THIENYL)ETHENYL)-

Systematic Name