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
Thumb
Weight
Average: 382.53
Monoisotopic: 382.227774334
Chemical Formula
C26H28N3
Synonyms
Not Available

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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 [L789].

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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Pyrvinium pamoate310X6S84LW3546-41-6OOPDAHSJBRZRPH-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Vanquin Suspension 50mg/5mlSuspension50 mg / 5 mLOralPfizer Canada Inc., Consumer Healthcare Division1994-12-312005-02-17Canada flag

Categories

ATC Codes
P02CX01 — Pyrvinium
Drug Categories
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]
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
PhaseStatusPurposeConditionsCount
1RecruitingTreatmentResectable 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 v81

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuspensionOral
Pill
SuspensionOral50 mg / 5 mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000288 mg/mLALOGPS
logP2.04ALOGPS
logP1.41ChemAxon
logS-6.2ALOGPS
pKa (Strongest Basic)1.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.05 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity136.12 m3·mol-1ChemAxon
Polarizability47.31 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at September 14, 2010 16:21 / Updated at June 19, 2021 00:26