8022. Pyrvinium Pamoate

Nomenclature

CAS number: 3546-41-6
6-(Dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methylquinolinium salt with 4,4′-methylenebis[3-hydroxy-2-naphthalenecarboxylic acid] (2:1); bis[6-(dimethylamino)-2-[2-(2,5-dimethyl-1-phenylpyrrol-3-yl)vinyl]-1-methylquinolinium] 4,4′-methylenebis(3-hydroxy-2-naphthoate); 6-(dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-3-pyrryl)vinyl]-1-methylquinolinium salt of 2,2′-dihydroxy-1,1′-dinaphthylmethane-3,3′-dicarboxylic acid; pyrvinium embonate; viprynium embonate; Molevac (Parke-Davis); Povanyl (Clément-Thékan); Pyrcon (Meuselbach); Vanquin (Pfizer).
C75H70N6O6; mol wt 1151.39.
C 78.24%, H 6.13%, N 7.30%, O 8.34%.

Description and references

Cyanine dye. Prepn: E. F. Elslager, D. F. Worth, US 2925417 (1960 to Parke, Davis). Determn in pharmaceutical prepn: H. D. Beckstead, S. J. Smith, J. Pharm. Sci. 56, 390 (1967); by HPLC: U. G. G. Hennig et al., Arch. Toxicol. 60, 278 (1987). Clinical trial: R. A. Buchanan et al., Clin. Pharmacol. Ther. 16, 716 (1974). Clinical pharmacology: T. C. Smith et al., ibid. 19, 802 (1976). Review of use in Enterobius vermicularis infections: G. C. Cook, Gut 35, 1159-1162 (1994).

Chemical structure

Properties

Bright orange or orange-red to almost black precipitate, mp 210-215° (softens at 190°). Absorption max: 236, 356, 503 nm. Stable to heat, light and air. Slightly sol in chloroform, methoxyethanol; very slightly sol in alcohol. Practically insol in water, ether.

Derivative

Pyrvinium chloride.

Nomenclature

CAS number: 548-84-5
Viprynium chloride; SN-4395.
C26H28ClN3; mol wt 417.97.
C 74.71%, H 6.75%, Cl 8.48%, N 10.05%.

Description and references

Prepn: E. Van Lare, L. G. S. Brooker, US 2515912 (1950 to Eastman Kodak).

Properties

May occur as dihydrate, deep-red powder, dec 249-251°. Sparingly sol in water.

Therapeutic Category

Anthelmintic (Nematodes).

Keywords

Anthelmintic (Nematodes)