Pyrvinium

Identification

Name
Pyrvinium
Accession Number
DB06816
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Pyrvinium pamoate310X6S84LW3546-41-6OOPDAHSJBRZRPH-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vanquin Suspension 50mg/5mlSuspension50 mgOralPfizer Canada Inc., Consumer Healthcare Division1994-12-312005-02-17Canada
Categories
UNII
6B9991FLU3
CAS number
7187-62-4
Weight
Average: 382.53
Monoisotopic: 382.227774334
Chemical Formula
C26H28N3
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

Pharmacology

Indication

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

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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:23061049]
  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. [PubMed:25003333]
  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
ChEBI
8687
ChEMBL
CHEMBL1201303
Wikipedia
Pyrvinium
ATC Codes
P02CX01 — Pyrvinium

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SuspensionOral50 mg
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

Taxonomy

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
Aminoquinoline / 1-phenylpyrrole / Quinoline / Tertiary aliphatic/aromatic amine / Dialkylarylamine / Benzenoid / Pyridinium / Pyridine / Monocyclic benzene moiety / Heteroaromatic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolinium ion (CHEBI:8687)

Drug created on September 14, 2010 10:21 / Updated on November 02, 2018 08:50