Pyrvinium

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Pyrvinium
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
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Legal status
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Identifiers
CAS number 7187-62-4
ATC code P02CX01
PubChem CID 5281035
ChemSpider 21125
UNII 6B9991FLU3
ChEBI CHEBI:8687
ChEMBL CHEMBL1201303
Chemical data
Formula C26H28N3+
Mol. mass 382.52 g/mol

Pyrvinium 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[edit]

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[edit]

  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.  edit
  2. ^ PubChem: Pyrvinium
  3. ^ a b 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. ^ a b 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 (inactive 2014-08-12). PMID 15298733.  edit