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| Clinical data | |
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| AHFS/ Drugs.com | Micromedex Detailed Consumer Information |
| ATC code | |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard ( EPA) | |
| ECHA InfoCard | 100.020.543 |
| Chemical and physical data | |
| Formula | C26H28N3+ |
| Molar mass | 382.531 g·mol−1 |
| 3D model ( JSmol) | |
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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 (inactive 2024-02-17).
{{ cite journal}}: CS1 maint: DOI inactive as of February 2024 ( link) -
^ 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.
 | This antiinfective drug article is a stub. You can help Wikipedia by expanding it. |
|
| |
| Clinical data | |
|---|---|
| AHFS/ Drugs.com | Micromedex Detailed Consumer Information |
| ATC code | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard ( EPA) | |
| ECHA InfoCard | 100.020.543 |
| Chemical and physical data | |
| Formula | C26H28N3+ |
| Molar mass | 382.531 g·mol−1 |
| 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 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 (inactive 2024-02-17).
{{ cite journal}}: CS1 maint: DOI inactive as of February 2024 ( link) -
^ 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.
|
| This antiinfective drug article is a stub. You can help Wikipedia by expanding it. |