Pyrvinium

Pyrvinium (Viprynium) is an anthelmintic effective for pinworms.^[1] Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate.^[2][3] Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.^[4][5]

Pyrvinium

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	P02CX01 (WHO)
Identifiers
IUPAC name 2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
CAS Number	7187-62-4
PubChem CID	5281035
ChemSpider	21125
UNII	6B9991FLU3
KEGG	C07412
ChEBI	CHEBI:8687
ChEMBL	ChEMBL1201303
CompTox Dashboard (EPA)	DTXSID4023545
ECHA InfoCard	100.020.543
Chemical and physical data
Formula	C26H28N3+
Molar mass	382.531 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=C(N1C2=CC=CC=C2)C)/C=C/C3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C
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 Key:QMHSXPLYMTVAMK-UHFFFAOYSA-N

Pyrvinium salts can also inhibit the growth of cancer cells.^[6] More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.^[7]

Synthesis

One synthetic method is based on Skraup synthesis and Paal-Knorr synthesis.^[6] More recently, an alternative convergent, synthetic strategy to pyrvinium triflate salts through Friedländer synthesis was reported.^[3]