| Identification | Back Directory | [Name]
PYRVINIUM PAMOATE | [CAS]
3546-41-6 | [Synonyms]
tru
povan
pyrcon
Poquil
sn-4395
tolapin
vanquin
povanyl
pamovin
alnoxin
altolat
molevac
Pyrvinium
Nsc223622
Neooxypaat
Vermitibier
neo-oxypate
pirviniumpamoate
vipryniumembonate
PYRVINIUM PAMOATE
pyrviniumembonate
PyrviniumChloride
PYRVINIUMPAMOATE,USP
Vipyrvinium embonate
PYRVINIUM PAMOATE 95%
Pyrvinium Pamoate (500 mg)
PYRVINIUM PAMOATE USP/EP/BP
Pyrvinium pamoate salt hydrate
pyrvinium4,4’-methylenebis(3-hydroxynaphthalene-2-carboxylate)
methyl-,saltwith4,4’-methylenebis(3-hydroxy-2-naphthoicacid)(2:1)
6-(dimethylamino)-2-(2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl)-1-quinoliniu
6-Dimethylamino-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methylquinolinium
6-(Dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methylquinolinium
bis(6-dimethylamino-2-(2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl)-1-methylquinolinium) 3,3-dihydroxy-4,4-methylenedi-2-naphthoate
6-(Dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methyl-4,4′-methylenebis[3-hydroxy-2-naphthalenecarboxylate] (2:1)-quinolinium | [EINECS(EC#)]
222-596-3 | [Molecular Formula]
C75H70N6O6 | [MDL Number]
MFCD00010090 | [MOL File]
3546-41-6.mol | [Molecular Weight]
1151.39 |
| Chemical Properties | Back Directory | [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. ]
room temp | [solubility ]
DMSO: >10mg/mL | [form ]
powder | [color ]
red | [EPA Substance Registry System]
Pyrvinium pamoate (3546-41-6) |
| Hazard Information | Back Directory | [Uses]
anthelmintic | [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. | [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. | [Definition]
ChEBI: Pyrvinium pamoate is a naphthoic acid. It has a role as an anticoronaviral agent. | [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. | [storage]
4°C, protect from light ,unstable in solution, ready to use. |
| Questions And Answer | Back Directory | [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.
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