Pyrvinium Explained

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] Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.^{[3] [4]}

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.^[5]

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.^[7]

Notes and References

1. Desai AS . Single-dose treatment of oxyuriasis with pyrvinium embonate . British Medical Journal . 2 . 5319 . 1583–5 . December 1962 . 14027194 . 1926864 . 10.1136/bmj.2.5319.1583 .
2. Web site: Pyrvinium . PubChem . U.S. National Library of Medicine .
3. Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP . Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling . PLOS ONE . 5 . 11 . e15521 . 2010 . 21170416 . 2993965 . 10.1371/journal.pone.0015521 . 2010PLoSO...515521S . free .
4. Shen C, Nayak A, Melendez RA, Robbins DJ . Casein Kinase 1α as a Regulator of Wnt-Driven Cancer . International Journal of Molecular Sciences . 21 . 16 . 5940 . 2020 . 32824859 . 7460588 . 10.3390/ijms21165940 . free .
5. Esumi H, Lu J, Kurashima Y, Hanaoka T . 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 . 685–90 . August 2004 . 15298733 . 10.1111/j.1349-7006.2004.tb03330.x . free . 11159109 .
6. WO . 2006078754 . Novel Quinolinium Salts and Derivatives. Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F . 2006-07-27 .
7. Mao Y, Lin N, Tian W, Huang Z . Heterocycles . 85 . 5 . 2012 . 1179–1185 . 10.3987/COM-12-12446. New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway . 2024-02-17 . free .