Pyrvinium

Identification

Summary

Pyrvinium is an anthelmintic agent used for the treatment of pinworm infestations.

Generic Name

Pyrvinium

DrugBank Accession Number

DB06816

Background

Pyrvinium is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate. Pyrvinum's anti-cancer properties are currently under investigation.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Pyrvinium (DB06816)

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Weight

Average: 382.53
Monoisotopic: 382.227774334

Chemical Formula

C₂₆H₂₈N₃

Synonyms

Not Available

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Pharmacology

Indication

Pyrvinium was once used in the treatment of pinworm infestations ³.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Enterobius vermicularis infection		••••••••••••			••••••••••

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Pharmacodynamics

Pyrvinium is an anthelmintic agent which acts to kill pinworms ³.

Mechanism of action

Pyrvinium is believed to interfere with glucose uptake by pinworms ³.

Pyrvinium is also thought to inhibit mitochondrial respiration complex 1 and suppress the unfolded protein response ¹. It is also believed to supress the Wnt pathway by activating casein kinase 1α. These properties have led to the investigation of pyrvinium's activity against cancers like intestinal polyposis ².

Absorption

Pyrvinium is not significantly absorbed from the gastrointestinal tract ⁴.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

No interactions found.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Pyrvinium pamoate	310X6S84LW	3546-41-6	OOPDAHSJBRZRPH-UHFFFAOYSA-N

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Vanquin Suspension 50mg/5ml	Suspension	50 mg / 5 mL	Oral	Pfizer Canada Inc., Consumer Healthcare Division	1994-12-31	2005-02-17

Categories

ATC Codes

P02CX01 — Pyrvinium

• P02CX — Other antinematodals
• P02C — ANTINEMATODAL AGENTS
• P02 — ANTHELMINTICS
• P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Drug Categories

• Anthelmintics
• Anti-Infective Agents
• Antinematodal Agents
• Antiparasitic Agents
• Antiparasitic Products, Insecticides and Repellents
• Heterocyclic Compounds, Fused-Ring
• Quinolines
• Quinolinium Compounds

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Aminoquinolines and derivatives / Dialkylarylamines / Pyridinium derivatives / Benzene and substituted derivatives / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations

Substituents

1-phenylpyrrole / Amine / Aminoquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolinium ion (CHEBI:8687)

Affected organisms

Not Available

Chemical Identifiers

UNII

6B9991FLU3

CAS number

7187-62-4

InChI Key

QMHSXPLYMTVAMK-UHFFFAOYSA-N

InChI

InChI=1S/C26H28N3/c1-19-17-21(20(2)29(19)24-9-7-6-8-10-24)11-13-23-14-12-22-18-25(27(3)4)15-16-26(22)28(23)5/h6-18H,1-5H3/q+1

IUPAC Name

2-[(E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-6-(dimethylamino)-1-methylquinolin-1-ium

SMILES

CN(C)C1=CC2=C(C=C1)[N+](C)=C(\C=C\C1=C(C)N(C(C)=C1)C1=CC=CC=C1)C=C2

References

General References

1. Ishii I, Harada Y, Kasahara T: Reprofiling a classical anthelmintic, pyrvinium pamoate, as an anti-cancer drug targeting mitochondrial respiration. Front Oncol. 2012 Oct 2;2:137. doi: 10.3389/fonc.2012.00137. eCollection 2012. [Article]
2. Li B, Flaveny CA, Giambelli C, Fei DL, Han L, Hang BI, Bai F, Pei XH, Nose V, Burlingame O, Capobianco AJ, Orton D, Lee E, Robbins DJ: Repurposing the FDA-approved pinworm drug pyrvinium as a novel chemotherapeutic agent for intestinal polyposis. PLoS One. 2014 Jul 8;9(7):e101969. doi: 10.1371/journal.pone.0101969. eCollection 2014. [Article]
3. Sheth UK (1975). Mechanisms of Anthelmintic Action. In Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Volume 19 (pp. 152). Birkhäuser Basel. [ISBN:978-3-0348-7090-0]
4. HSDB: Pyrvinium [Link]

External Links

Human Metabolome Database

HMDB0240273

KEGG Compound

C07412

PubChem Compound

5281035

PubChem Substance

310264894

ChemSpider

21125

RxNav

35163

ChEBI

8687

ChEMBL

CHEMBL1201303

ZINC

ZINC000003831401

Wikipedia

Pyrvinium

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
1	Recruiting	Treatment	Resectable Pancreatic Ductal Adenocarcinoma (PDAC) / Stage 0 Pancreatic Cancer AJCC v8 / Stage I Pancreatic Cancer AJCC v8 / Stage IA Pancreatic Cancer AJCC v8 / Stage IB Pancreatic Cancer AJCC v8 / Stage II Pancreatic Cancer AJCC v8 / Stage IIA Pancreatic Cancer AJCC v8 / Stage IIB Pancreatic Cancer AJCC v8	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Suspension	Oral	50 ml
Suspension	Oral
Pill
Suspension	Oral	50 mg / 5 mL

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000288 mg/mL	ALOGPS
logP	2.04	ALOGPS
logP	1.41	Chemaxon
logS	-6.2	ALOGPS
pKa (Strongest Basic)	1.48	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	12.05 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	136.12 m3·mol-1	Chemaxon
Polarizability	47.31 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	224.8478663	predicted	DarkChem Lite v0.1.0
[M-H]-	226.6672663	predicted	DarkChem Lite v0.1.0
[M-H]-	192.22743	predicted	DeepCCS 1.0 (2019)
[M+H]+	225.1501663	predicted	DarkChem Lite v0.1.0
[M+H]+	227.4937663	predicted	DarkChem Lite v0.1.0
[M+H]+	194.623	predicted	DeepCCS 1.0 (2019)
[M+Na]+	224.6546663	predicted	DarkChem Lite v0.1.0
[M+Na]+	226.6432663	predicted	DarkChem Lite v0.1.0
[M+Na]+	200.53552	predicted	DeepCCS 1.0 (2019)

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Drug created at September 14, 2010 16:21 / Updated at February 02, 2024 22:54