PYRANTEL

US Approved OTC

First approved in 1971

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

Structure Search

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+

HIDE SMILES / InChI

Description
Sources: https://web.archive.org/web/20171115074121/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061808.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/monograph/pyrantel-pamoate.html

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 Target ID: Nicotinic receptors (AChRs) of nematodes Sources: https://www.ncbi.nlm.nih.gov/pubmed/7535704 \| https://www.ncbi.nlm.nih.gov/pubmed/11489460	Agonist 2752
Mouse α2βεδ AChRs 3 Target ID: Mouse α2βεδ AChRs Sources: https://www.ncbi.nlm.nih.gov/pubmed/11489460	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Strongyloidiasis 10 Sources: https://web.archive.org/web/20171115074121/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061808.pdf	Curative	Approved 8583	Strongid Approved Use Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies. Launch Date 1990
Pinworm infection 3 Sources: https://web.archive.org/web/20171115074121/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061808.pdf	Curative	Approved 8583	Strongid Approved Use Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies. Launch Date 1990
Large roundworms infection 3 Sources: https://web.archive.org/web/20171115074121/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061808.pdf	Curative	Approved 8583	Strongid Approved Use Drug is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); and large roundworms (Parascaris equorum) in horses and ponies. Launch Date 1990
Tapeworm infection 8 Sources: https://web.archive.org/web/20171115074121/https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm061808.pdf	Curative	Approved 8583	Strongid Approved Use Pyrantel pamoate is indicated for the removal and control of mature infections of large strongyles (Strongylus vulgaris, S. edentatus, S. equinus); small strongyles; pinworms (Oxyuris equi); large roundworms (Parascaris equorum) and tapeworms (Anoplocephala perfoliata) in horses and ponies. Launch Date 1990

C_max

Value	Dose	Co-administered	Analyte	Population
0.09 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11348490/	13.3 mg/kg single, oral dose: 13.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRANTEL plasma	Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1.06 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11348490/	13.3 mg/kg single, oral dose: 13.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRANTEL plasma	Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11348490/	13.3 mg/kg single, oral dose: 13.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		PYRANTEL plasma	Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 389 CYP2C8 810 CYP1A2 1197 CYP2A6 626 CYP1B1 104 CYP2B6 776 CYP2C19 1119 CYP2E1 729 CYP3A5 446 CYP4A11 137

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes

Sourcing

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

PubMed

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

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.

Name

Type

Language

PYRANTEL

Official Name

English

KONVERMEX

Preferred Name

English

pyrantel [INN]

Common Name

English

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

Systematic Name

English

PYRANTEL [HSDB]

Common Name

English

PYRANTEL [VANDF]

Common Name

English

Pyrantel [WHO-DD]

Common Name

English

PYRANTEL [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.1871