Pyrvinium

Pyrvinium

File:Pyrvinium.png
Systematic (IUPAC) name
2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Identifiers
CAS Number	7187-62-4
ATC code	P02CX01 (WHO)
PubChem	CID: 5281035
ChemSpider	21125
UNII	6B9991FLU3
ChEBI	CHEBI:8687
ChEMBL	CHEMBL1201303
Chemical data
Formula	C26H28N3+
Molecular mass	382.52 g/mol
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 is an anthelmintic effective for pinworms. Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate.

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

Synthesis

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