PYRVINIUM CHLORIDE DIHYDRATE

First approved in 1955

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H28N3.Cl.2H2O
Molecular Weight	454.004
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of PYRVINIUM CHLORIDE DIHYDRATE

Structure Search

SMILES

O.O.[Cl-].CN(C)C1=CC2=CC=C(\C=C\C3=C(C)N(C(C)=C3)C4=CC=CC=C4)[N+](C)=C2C=C1

InChI

InChIKey=BSFRPKBHTPMTGV-UHFFFAOYSA-M

InChI=1S/C26H28N3.ClH.2H2O/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;1H;2*1H2/q+1;;;/p-1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	Cl
Molecular Weight	35.453
Charge	-1
Count

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

Molecular Formula	C26H28N3
Molecular Weight	382.5206
Charge	1
Count

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

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 1447
Cryptosporidium parvum 5 Target ID: CHEMBL612855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18591280	Inhibitor 8504	354.0 nM [IC50]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24354286 \| https://www.ncbi.nlm.nih.gov/pubmed/19363158	Antagonist 2849

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 66 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 8583	POVAN Approved Use Pyrvinium is used to treat pinworms (enterobiasis).
Prostate cancer 186 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 1079 OATP1B3 961 Ca2+ activated K+ channel 17

Drug as perpetrator

Target	Modality	Activity
CYP3A4/5 357	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/26265743/	yes
Ca2+ activated K+ channel 17	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22814238/	yes
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 970	inhibitor 4027 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
The impact of pyrvinium pamoate on colon cancer cell viability.	2014-10	25060218
Absorption of pyrvinium pamoate.	1976-06	1269218

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:43 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:43 GMT 2025`
Record UNII	3XL8T5I39L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PYRVINIUM CHLORIDE DIHYDRATE

Common Name

English

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

Preferred Name

English

Code System Code Type Description

PUBCHEM

12314839

Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025

PRIMARY

FDA UNII

3XL8T5I39L

Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025

PRIMARY

CAS

6151-23-1

Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025

PRIMARY

Related Record Type Details


					MT7O310S39

PYRVINIUM CHLORIDE

ANHYDROUS->SOLVATE


					6B9991FLU3

PYRVINIUM

PARENT -> SALT/SOLVATE

Related Record Type Details


					6B9991FLU3

PYRVINIUM

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: 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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

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

Drug as perpetrator