PYRVINIUM PAMOATE

First approved in 1955

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C26H28N3.C23H16O6
Molecular Weight	1153.4108
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	2

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.CN(C)C5=CC6=C(C=C5)[N+](C)=C(\C=C\C7=C(C)N(C(C)=C7)C8=CC=CC=C8)C=C6.OC(=O)C9=CC%10=C(C=CC=C%10)C(CC%11=C%12C=CC=CC%12=CC(C(O)=O)=C%11O)=C9O

InChI

InChIKey=OOPDAHSJBRZRPH-UHFFFAOYSA-N

InChI=1S/2C26H28N3.C23H16O6/c2*1-19-17-21(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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h2*6-18H,1-5H3;1-10,24-25H,11H2,(H,26,27)(H,28,29)/q2*+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
Absorption of pyrvinium pamoate.	1976 Jun	1269218
The impact of pyrvinium pamoate on colon cancer cell viability.	2014 Oct	25060218

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 PAMOATE

Common Name

English

NSC-223622

Code

English

POVAN

Brand Name

English

PYRVINIUM EMBONATE [MART.]

Common Name

English

Pyrvinium embonate [WHO-DD]

Common Name

English

PYRVINIUM PAMOATE [USP IMPURITY]

Common Name

English

6-(DIMETHYLAMINO)-2-(2-(2,5-DIMETHYL-1-PHENYLPYRROL-3-YL)VINYL)-1-METHYLQUINOLINIUM 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHOATE) (2:1)

Common Name

English

PYRVINIUM PAMOATE [USP-RS]

Common Name

English

PYRVINIUM EMBONATE

Common Name

English

PYRVINIUM PAMOATE [JAN]

Common Name

English

PYRVINIUM PAMOATE [MI]

Common Name

English

QUINOLINIUM, 6-(DIMETHYLAMINO)-2-(2-(2,5-DIMETHYL-1-PHENYL-1H-PYRROL-3-YL)ETHENYL)-1-METHYL-, SALT WITH 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACID) (2:1)

Common Name

English

PYRVINIUM (AS EMBONATE)

Common Name

English

PYRVINIUM PAMOATE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C250