Pyrvinium

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
ChEBI	CHEBI:8687
ChEMBL	CHEMBL1201303
Chemical and physical data
Formula	C26H28N3^+
Molar mass	382.52 g/mol
3D model (Jmol)	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 (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 salts can also inhibit the growth of cancer cells.^[4] More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.^[5]

Synthesis

One synthetic method is based on Skraup synthesis and Paal-Knorr synthesis.^[4] More recently, an alternative convergent, synthetic strategy to pyrvinium triflate salts through Friedländer synthesis was reported.^[3]

References

1. Desai, A. S. (1962). "Single-dose treatment of oxyuriasis with pyrvinium embonate". British Medical Journal. 2 (5319): 1583–1585. doi:10.1136/bmj.2.5319.1583. PMC 1926864. PMID 14027194.
2. PubChem: Pyrvinium
3. An, Jing; Mao, Yongjun; Lin, Nan; Tian, Wang; Huang, Ziwei (2012). "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles. 85 (5): 1179–1185. doi:10.3987/COM-12-12446.
4. WO 2006078754, J. E. Macdonald, M. K. Hysell, D. Yu, H. Li, and F. Wong-Staal, "Novel Quinolinium Salts and Derivatives", published 2006-07-27 
5. Esumi, H.; Lu, J.; Kurashima, Y.; Hanaoka, T. (2004). "Antitumor activity of pyrvinium pamoate, 6-(dimethylamino)-2-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl-1-methyl-quinolinium pamoate salt, showing preferential cytotoxicity during glucose starvation". Cancer science. 95 (8): 685–690. doi:10.1111/j.1349-7006.2004.tb03330.x. PMID 15298733.