BEPHENIUM HYDROXYNAPHTHOATE Chemical Properties

Melting point:

170-171°

storage temp. 

Store at -20°C

solubility 

≥ 20.85mg/mL in DMSO

Safety Information

WGK Germany 

3

MSDS

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BEPHENIUM HYDROXYNAPHTHOATE Usage And Synthesis

Pharmacology and mechanism of action

Bephenium is a quaternary ammonium compound first introduced into clinical medicine in 1958. It has a wide anthelminthic activity, in particular against Ancylostoma duodenale and Ascaris lumbricoides.
The mechanism of action of bephenium is similar to that of pyrantel and levamisole (see the monograph on levamisole, p. 74).
 

Indications

Infections with Ancylostoma duodenale, Ascaris lumbricoides and Necator americanus. Superior alternative drugs are available today.
 

Side effects

The drug has a bitter taste which might cause some patients especially children to refuse intake or vomit. This may be minimized by giving the drug with a sweet drink. Some individuals experience transient nausea, vomiting and headache after drug intake. Vertigo is occasionally reported.
 

Contraindications

There are no known contraindications to the drug.
 

Interactions

Bephenium has antagonistic effects to piperazine. However, no interactions were reported when the two drugs were combined together during helminthic therapy ^[1].
 

Preparations

5 g bephenium hydroxynaphthoate contains 2.9 g bephenium.

• Alcopar® (Wellcome). Sachet containing 5 g of bephenium hydroxynaphthoate.

References

1. Goodwin LG, Jayewardene LG, Standen OD (1958). Clinical trials with bephenium hydroxynaphthoate against hookworm in Ceylon. BMJ, 2, 1572–1576.

Uses

antibacterial, antilepretic, antituberculosis

Uses

Bephenium Hydroxynapthoate is an anthelmintic agent used to treat hookworm infections and ascariasis.

Indications

This drug exhibits antihelmintic action by acting as a cholinergic agonist, causing paralysis of the parasite musculature. This facilitates its removal from the intestines. It is used for treating ascariasis, ankylostomiasis, enterobiasis, trichostrongyliasis, and tricocefalosis. A single dose of bephenium heals from 80 to 100% of patients infected with A. duodenale. It is less effective with respect to N. americanus. Synonyms of this drug are aclopar and others.

Clinical Use

Bephenium can be used against Ascaris, Ancylostoma, and Trichostrongylus infections; it is less effective against Necator. Occasional adverse reactions occur: nausea, diarrhea, vomiting, headache, vertigo.

Synthesis

Bephenium, 3-hydroxy-2-naphthoat benzyldimethyl(2-phenoxyethyl) ammonia (38.1.37), is made by reacting the sodium salt of 3-hydroxy-2-naphthoic acid with benzyldimethyl(2-phenoxyethyl)ammonia chloride (38.1.36). This is in turn made from benzyl chloride and N-(2-phenoxyethyl)dimethylamine (38.1.35), which is synthesized by reacting sodium phenolate with 2-dimethylaminoethylchloride.

BEPHENIUM HYDROXYNAPHTHOATE(3818-50-6)Related Product Information

• Phenoxybenzamine hydrochloride
• 2-(Phenylmethoxy)-naphthalene
• benzyl(2-hydroxyethyl)dimethylammonium hydroxide
• DIETHYLAMINE SALICYLATE
• Tetramethylammonium acetate
• TETRAMETHYLAMMONIUM BENZOATE
• 3-Hydroxy-2-naphthoic acid
• Choline salicylate
• Benzyltrimethylammonium hydroxide
• BENZYLTRIMETHYLAMMONIUM METHOXIDE
• BEPHENIUM HYDROXYNAPHTHOATE