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;
KEGG	C07412;
ChEBI	CHEBI:8687;
ChEMBL	ChEMBL1201303;
CompTox Dashboard (EPA)	DTXSID4023545 ;
ECHA InfoCard	100.020.543
Chemical and physical data
Formula	C26H28N3+
Molar mass	382.531 g·mol−1
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 (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 was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α.^[4]^[5]

Pyrvinium salts can also inhibit the growth of cancer cells.^[6] More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.^[7]

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.^[3]

References

^ Desai AS (December 1962). "Single-dose treatment of oxyuriasis with pyrvinium embonate". British Medical Journal. 2 (5319): 1583–5. doi:10.1136/bmj.2.5319.1583. PMC 1926864. PMID 14027194.
^ "Pyrvinium". PubChem. U.S. National Library of Medicine.
^ ^a ^b Mao Y, Lin N, Tian W, Huang Z (2012). "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles. 85 (5): 1179–1185. doi:10.3987/COM-12-12446.
^ Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP (2010). "Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling". PLOS ONE. 5 (11): e15521. Bibcode:2010PLoSO...515521S. doi:10.1371/journal.pone.0015521. PMC 2993965. PMID 21170416. This article incorporates text from this source, which is available under the CC0 license.
^ Shen C, Nayak A, Melendez RA, Robbins DJ (2020). "Casein Kinase 1α as a Regulator of Wnt-Driven Cancer". International Journal of Molecular Sciences. 21 (16): 5940. doi:10.3390/ijms21165940. PMC 7460588. PMID 32824859.
^ ^a ^b WO 2006078754, Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F, "Novel Quinolinium Salts and Derivatives", published 2006-07-27
^ Esumi H, Lu J, Kurashima Y, Hanaoka T (August 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): 685–90. doi:10.1111/j.1349-7006.2004.tb03330.x. PMC 11159109. PMID 15298733.

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[1] Desai AS (December 1962). "Single-dose treatment of oxyuriasis with pyrvinium embonate". British Medical Journal. 2 (5319): 1583–5. doi:10.1136/bmj.2.5319.1583. PMC 1926864. PMID 14027194.

[2] "Pyrvinium". PubChem. U.S. National Library of Medicine.

[Heterocycles-3] Mao Y, Lin N, Tian W, Huang Z (2012). "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles. 85 (5): 1179–1185. doi:10.3987/COM-12-12446.

[4] Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP (2010). "Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling". PLOS ONE. 5 (11): e15521. Bibcode:2010PLoSO...515521S. doi:10.1371/journal.pone.0015521. PMC 2993965. PMID 21170416. This article incorporates text from this source, which is available under the CC0 license.

[5] Shen C, Nayak A, Melendez RA, Robbins DJ (2020). "Casein Kinase 1α as a Regulator of Wnt-Driven Cancer". International Journal of Molecular Sciences. 21 (16): 5940. doi:10.3390/ijms21165940. PMC 7460588. PMID 32824859.

[Macdonald-6] WO 2006078754, Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F, "Novel Quinolinium Salts and Derivatives", published 2006-07-27

[7] Esumi H, Lu J, Kurashima Y, Hanaoka T (August 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): 685–90. doi:10.1111/j.1349-7006.2004.tb03330.x. PMC 11159109. PMID 15298733.

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