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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 of PYRVINIUM

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

Molecular Formula C26H28N3
Molecular Weight 382.5206
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
354.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Primary
Unknown
Curative
POVAN
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Sourcing

PubMed

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
Record UNII
6B9991FLU3
Record Status Validated (UNII)
Record Version