Pyrvinium
From Wikipedia, the free encyclopedia
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|---|---|
| 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 |
| Legal status | ? |
| Identifiers | |
| CAS number | 7187-62-4 |
| ATC code | P02CX01 |
| PubChem | CID 5281035 |
| 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
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
- ↑ 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.
- ↑ PubChem: Pyrvinium
- ↑ 3.0 3.1 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.
- ↑ 4.0 4.1 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
- ↑ 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.
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