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

Molecular Formula	C11H14N2S
Molecular Weight	206.307
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 2678
Mouse α2βεδ AChRs 3 Target ID: Mouse α2βεδ AChRs Sources: https://www.ncbi.nlm.nih.gov/pubmed/11489460	Agonist 2678

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 8429	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 8429	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 8429	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 8429	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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 349 CYP2C8 693 CYP1A2 1054 CYP2A6 543 CYP1B1 92 CYP2B6 664 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP4A11 119

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP1B1 92	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	no
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/12920490/	yes
CYP2D6 1217	substrate 3367 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
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.	2001 Jan	11124226
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:45:38 GMT 2023` Edited by `admin` on `Sat Dec 16 16:45:38 GMT 2023`
Record UNII	4QIH0N49E7
Record Status	`Validated (UNII)`
Record Version

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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

English

PYRANTEL [HSDB]

Common Name

English

PYRANTEL [VANDF]

Common Name

English

Pyrantel [WHO-DD]

Common Name

English

PYRANTEL [MI]

Common Name

English

KONVERMEX

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 520.1871