3546-41-6

Basic information

• Product Name: PYRVINIUM PAMOATE
• Synonyms: 6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl)-1-quinoliniu;alnoxin;altolat;methyl-,saltwith4,4’-methylenebis(3-hydroxy-2-naphthoicacid)(2:1);molevac;neo-oxypate;pamovin;pirviniumpamoate
• CAS NO: 3546-41-6
• Molecular Formula: C75H70N6O6
• Molecular Weight: 1151.39
• EINECS: 222-596-3
• Product Categories: POVAN
• Mol File: 3546-41-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 210-215° (softens at 190°)
• Boiling Point: 829.27°C (rough estimate)
• Appearance: red/
• Density: 1.0104 (rough estimate)
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: room temp
• Solubility: DMSO: >10mg/mL
• CAS DataBase Reference: PYRVINIUM PAMOATE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRVINIUM PAMOATE(3546-41-6)
• EPA Substance Registry System: PYRVINIUM PAMOATE(3546-41-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3546-41-6(Hazardous Substances Data)

Usage

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.

Uses

Different sources of media describe the Uses of 3546-41-6 differently. You can refer to the following data:
1. anthelmintic
2. Pyrvinium Pamoate is a potent noncompetitive inhibitor of the androgen receptor, with the application towards prostate cancer treatment. Antihelmintic.

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.

InChI:InChI=1/2C26H28N3.C23H16O6/c2*1-19-17-21(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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h2*6-18H,1-5H3;1-10,24-25H,11H2,(H,26,27)(H,28,29)/q2*+1;/p-2

Upstream product

• 99-98-9 4-amino-N,N-dimethylaniline 
• 6640-22-8 embonic acid disodium salt 
• 35648-29-4 (E)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)-6-(dimethylamino)-1-methylquinolin-1-ium iodide 
• 92-99-9 6-(N,N-dimethylamino)-2-methylquinoline 
• 61791-77-3 (E)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl]-1-methyl-6-(dimethylamino)quinolinium methyl sulphate salt 

Relevant articles and documents

Synthesis and efficacy of pyrvinium-inspired analogs against tuberculosis and malaria pathogens

Herein, we report the synthesis and evaluation of pyrvinium-based antimalarial and antitubercular compounds. Pyrvinium is an FDA approved drug for the treatment of pinworm infection, and it has been reported to have antiparasitic and antimicrobial activities. Pyrvinium contains quinoline core coupled with pyrrole. We replaced the pyrrole with various aryl or heteroaryl substituents to generate pyrvinium analogs. The profiling of these compounds against malaria parasite P. falciparum 3D7 revealed analogs with better antimalarial activity than pyrvinium pamoate. Compound 14 and 16 showed IC50 of 23 nM and 60 nM against P. falciparum 3D7, respectively. These compounds were also effective against drug-resistant malaria parasite P. falciparum Dd2 with IC50 of 53 nM and 97 nM, respectively. The cytotoxicity against CHO-K1, HEK and NRK-49F cells revealed better selectivity index for these new analogs compared to pyrvinium. Additionally, this series of compounds showed activity against M. tuberculosis H37Rv; particularly compounds 10, 13, 14 and 16 showed equipotent antitubercular activity to that of pyrvinium pamoate. The compounds 14 and 16 should be taken forward as leads for further optimization.