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;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C26H28N3+
Molar mass	382.52 g/mol
3D model (JSmol)	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 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

↑ PMID 14027194 (PMID 14027194)
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↑ 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
↑ PMID 15298733 (PMID 15298733)
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Template:Anthelmintics

Template:Antiinfective-drug-stub

[1] PMID 14027194 (PMID 14027194)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[2] PubChem: Pyrvinium

[Heterocycles-3] 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.

[Macdonald-4] 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

[5] PMID 15298733 (PMID 15298733)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[1]

[2]

[3]

[4]

[5]

Pyrvinium

Synthesis

References

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