Pyrvinium

Pyrvinium
Clinical data
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ATC code
Identifiers
CAS Number
PubChem CID
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UNII
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ChEMBL
Chemical and physical data
Formula C26H28N3+
Molar mass 382.52 g/mol
3D model (JSmol)

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. PMC 1926864 Freely accessible. PMID 14027194. doi:10.1136/bmj.2.5319.1583.
  2. ↑ PubChem: Pyrvinium
  3. 1 2 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. 1 2 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. PMID 15298733. doi:10.1111/j.1349-7006.2004.tb03330.x.


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