Pyrvinium

Short description: Chemical compound

Pyrvinium

Clinical data
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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

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

1. ↑ "Single-dose treatment of oxyuriasis with pyrvinium embonate". British Medical Journal 2 (5319): 1583–5. December 1962. doi:10.1136/bmj.2.5319.1583. PMID 14027194.
2. ↑ "Pyrvinium". PubChem. U.S. National Library of Medicine. https://www.ncbi.nlm.nih.gov/pccompound/?term=Pyrvinium.
3. ↑ 3.0 3.1 "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles 85 (5): 1179–1185. 2012. doi:10.3987/COM-12-12446.
4. ↑ "Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling". PLOS ONE 5 (11): e15521. 2010. doi:10.1371/journal.pone.0015521. PMID 21170416. Bibcode: 2010PLoSO...515521S.
5. ↑ "Casein Kinase 1α as a Regulator of Wnt-Driven Cancer". International Journal of Molecular Sciences 21 (16): 5940. 2020. doi:10.3390/ijms21165940. PMID 32824859.
6. ↑ 6.0 6.1 Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F, "Novel Quinolinium Salts and Derivatives", WO patent 2006078754, published 2006-07-27
7. ↑ "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. August 2004. doi:10.1111/j.1349-7006.2004.tb03330.x. PMID 15298733.

* v
* t
* e

Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)

Antiplatyhelmintic agents|

| Antitrematodals
(schistosomicides)|

| Binds tubulin|

* benzimidazole
* Triclabendazole#

|

AI|

* phosphonic acid
* Metrifonate‡

Other/unknown|

* quinoline
* Praziquantel#
* Oxamniquine#
* phenol
* Bithionol
* thiazole
* Niridazole
* arylsulfonate
* Stibophen

Anticestodals
(taeniacides)|

| Binds tubulin|

* benzimidazole
* Albendazole#

|

Other/unknown|

* quinoline
* Praziquantel#
* salicylanilide
* Niclosamide#
* aminoacridine
* Quinacrine
* butyrophenone
* Desaspidin
* chlorophenol
* Dichlorophen

Antinematodal agents
(including
macrofilaricides)|

| Binds tubulin|

* benzimidazole
* Mebendazole#
* Albendazole#
* Tiabendazole
* Fenbendazole
* Ciclobendazole
* Flubendazole

|

Glutamate-gated chloride channel, GABA receptor|

* avermectins
* Abamectin
* Doramectin
* Emamectin
* Ivermectin#
* Selamectin
* milbemycins
* Moxidectin
* Milbemycin oxime

NMDA|

* tetrahydropyrimidine
* Pyrantel#
* pyrantel pamoate
* Oxantel
* Morantel
* Carbantel
* Febantel (aka felsantel)

Other/unknown|

* piperazine
* Piperazine
* Diethylcarbamazine#
* thiazole
* Levamisole#
* quinolinium
* Pyrvinium
* benzylammonium
* Bephenium
* naphthalenesulfonate
* Suramin#
* Tribendimidine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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