PYRVINIUM PAMOATE Chemical Properties

Melting point:

210-215° (softens at 190°)

Boiling point:

829.27°C (rough estimate)

Density 

1.0104 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

2-8°C

solubility 

DMSO: >10mg/mL

form 

powder

color 

red

EPA Substance Registry System

Pyrvinium pamoate (3546-41-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933492250

PYRVINIUM PAMOATE Usage And Synthesis

Pharmacology and mechanism of action

Pyrvinium is a quaternary ammonium derivative of a cyanine dye with marked effect against Enterobius vermicularis.
The mechanism of action is not well known. The drug inhibits oxidative metabolism in the worms and interferes with the absorption of glucose in intestinal helminths. Since most intestinal worms are dependent on anaerobic carbohydrate metabolism, this may be an important action of the drug^[1].
 

Indications

Infections caused by Enterobius vermicularis. Pyrvinium is largely replaced today by more effective and safer drugs such as albendazole and mebendazole.
 

Side effects

Gastrointestinal disturbances such as nausea, vomiting, dyspepsia, indigestion and abdominal pain are frequent. Allergic reactions and photosensitivity have been reported. Pyrvinium stains the stool bright red and may stain clothing if vomiting occurs. Patients should be informed about this.
 

Preparations

Pyrvinium pamoate (embonate): 450 mg of the pamoate is equivalent to 300 mg of pyrvinium.
• Povanyl ® (Parke-Davis). Oral solution 10 mg pyrvinium per ml. Tablets 50 mg pyrvinium.
• Vanquin® (Parke-Davis). Oral solution 10 mg pyrvinium per ml. Tab pyrvinium.

References

1. Buchanan RA, Barrow WB, Heffelfinger JC, Kinkel AW, Smith TC, Turner JL (1974). Pyrvinium pamoate. Clin Pharmacol Ther, 16, 716–719.

Description

Pyrvinium is a tasteless, odorless, bright orange to black, crystalline solid. It is insoluble in water or ether, slightly soluble in chloroform, and soluble in glacial acetic acid.

Uses

anthelmintic

Uses

Pyrvinium Pamoate is a potent noncompetitive inhibitor of the androgen receptor, with the application towards prostate cancer treatment. Antihelmintic.

Definition

ChEBI: Pyrvinium pamoate is a naphthoic acid. It has a role as an anticoronaviral agent.

Indications

The cation is the active part of the compound. Pyrvinium is used against pinworms (Enterobius).

brand name

Povan (Parke-Davis).

General Description

Odorless bright orange or orange-red to brownish red or almost black fluffy powder. Melting point 210-215°C. Insoluble in water. Tasteless.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

PYRVINIUM PAMOATE is light sensitive. Incompatible with strong oxidizing agents, strong acids and bases .

Fire Hazard

Flash point data for PYRVINIUM PAMOATE are not available; however, PYRVINIUM PAMOATE is probably combustible.

Biochem/physiol Actions

Pyrvinium pamoate is a potent androgen receptor inhibitor. Androgen receptors (ARs) are nuclear hormone receptors/transcription factors that reside in the cytoplasm and activated by testosterone and dihydrotestosterone. AR inhibitors have potential therapeutic benefit in prostate cancer; competitive inhibitors and chemical castration methods have been discovered, but both therapies have undesirable side effects and/or resistance potential. A screen for non-competitive inhibitors was performed, resulting in the discovery of pyrvinium as an AR inhibitor. In comparison to competitive inhibitors, this compound does not bind to the ligand-binding domain of AR or block DNA occupancy by AR, but it inhibits AR-dependent gene expression via a distinct signaling mechanism. It is more potent than classical competitive AR antagonists and exhibits synergy with other AR inhibitors.

Side effects

Occasional adverse reactions are blood dyscrasia and folic acid deficiency. Rare adverse reactions are rash, vomiting, convulsion, shock, photosensitivity, and headache.

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