PYRVINIUM

First approved in 1955

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H28N3
Molecular Weight	382.5206
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C1=CC2=C(C=C1)[N+](C)=C(\C=C\C3=C(C)N(C(C)=C3)C4=CC=CC=C4)C=C2

InChI

InChIKey=QMHSXPLYMTVAMK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/cons/pyrvinium.html | https://www.ncbi.nlm.nih.gov/pubmed/20890287 | http://www.mayoclinic.org/drugs-supplements/pyrvinium-oral-route/proper-use/drg-20065693 | https://www.ncbi.nlm.nih.gov/pubmed/24354286

Pyrvinium (Viprynium) is an anthelmintic effective for pinworms. Pyrvinium is used in the treatment of enterobiasis caused by Enterobius vermicularis (pinworm). Pyrvinium has being shown to be a potent inhibitor of Wnt signaling (EC(50) of ∼10 nM). Pyrvinium binds all casein kinase 1 (CK1) family members in vitro at low nanomolar concentrations and pyrvinium selectively potentiates casein kinase 1α (CK1α) kinase activity. Pyrvinium pamoate (PP) is a potent noncompetitive inhibitor of the androgen receptor (AR). A noncompetitive AR inhibitor pyrvinium has significant potential to treat CRPC, including cancers driven by ligand-independent AR signaling.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Casein kinase I alpha 6 Target ID: CHEMBL2793 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20890287 \| https://www.ncbi.nlm.nih.gov/pubmed/25003333	Activator 1430
Cryptosporidium parvum 5 Target ID: CHEMBL612855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18591280	Inhibitor 8297	354.0 nM [IC50]
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24354286 \| https://www.ncbi.nlm.nih.gov/pubmed/19363158	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Cryptosporidiosis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18591280	Curative	Preclinical	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20890287 https://www.ncbi.nlm.nih.gov/pubmed/25060218 https://www.ncbi.nlm.nih.gov/pubmed/25003333	Primary	Basic research	Unknown Approved Use Unknown
Enterobiasis 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14162146 https://www.drugs.com/cons/pyrvinium.html http://www.mayoclinic.org/drugs-supplements/pyrvinium-oral-route/description/drg-20065693	Curative	Approved 8429	POVAN Approved Use Pyrvinium is used to treat pinworms (enterobiasis).
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24354286 https://www.ncbi.nlm.nih.gov/pubmed/19363158	Primary	Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 OATP1B3 706 Ca2+ activated K+ channel 16

Drug as perpetrator

Target	Modality	Activity
CYP3A4/5 335	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/26265743/	yes
Ca2+ activated K+ channel 16	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22814238/	yes
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8687	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8687
ZINC	ZINC000003831401	http://zinc15.docking.org/substances/ZINC000003831401

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

single 350-mg dose

Route of Administration: Oral

In Vitro Use Guide

Pyrvinium blocked colon cancer cell growth in vitro in a dose-dependent manner with great differences in the inhibitory concentration (IC(50)), ranging from 0.6 × 10(-6) to 65 × 10(-6) mol/L for colon cancer cells with mutations in WNT signaling.

Name

Type

Language

PYRVINIUM

Common Name

English

6-(DIMETHYLAMINO)-2-(2-(2,5-DIMETHYL-1-PHENYL-1H-PYRROL-3-YL)VINYL)-1-METHYLQUINOLINIUM

Systematic Name

English

PYRVINIUM CATION

Common Name

English

PYRVINUM (BASE)

Common Name

English

PYRVINIUM [HSDB]

Common Name

English

PYRVINIUM (CATION)

Common Name

English

QUINOLINIUM, 6-(DIMETHYLAMINO)-2-(2-(2,5-DIMETHYL-1-PHENYL-1H-PYRROL-3-YL)ETHENYL)-1-METHYL-

Systematic Name

English

PYRVINIUM ION

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

458314