Pyrvinium (Viprynium) is an

anthelmintic Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may a ...

effective for

pinworms Pinworm infection (threadworm infection in the UK), also known as enterobiasis, is a human parasitic disease caused by the pinworm. The most common symptom is itching in the anal area. The period of time from swallowing eggs to the appearanc ...

. Several forms of pyrvinium have been prepared with variable counter anions, such as

halide In chemistry, a halide (rarely halogenide) is a binary chemical compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluor ...

tosylate In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

triflate In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, ' ...

and

pamoate Pamoic acid, also called embonic acid, is a 2-Naphthoic acid derivative. Salts and esters of pamoic acid are known as pamoates or embonates. It can be prepared by the reaction of 3-hydroxy-2-naphthoic acid with formaldehyde. In pharmacology ...

. Pyrvinium was identified as a potent Wnt inhibitor, acting through activation of Casein kinase CK1α. Pyrvinium salts can also inhibit the growth of cancer cells. More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.

Synthesis

One synthetic method is based on

Skraup synthesis The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup (1850-1910). In the archetypal Skraup reaction, aniline is heated with sulfuric acid, glycerol, and an oxidizing agen ...

and Paal-Knorr synthesis. More recently, an alternative convergent, synthetic strategy to pyrvinium triflate salts through

Friedländer synthesis The Friedländer synthesis is a chemical reaction of 2-aminobenzaldehydes with ketones to form quinoline derivatives. It is named after German chemist Paul Friedländer (1857–1923). This reaction has been catalyzed by trifluoroacetic acid, t ...

was reported.

References

Anthelmintics Pyrroles Quinolines Quaternary ammonium compounds {{antiinfective-drug-stub