Difenidol

Absorption

Well absorbed from gastrointestinal tract following oral administration.

Toxicity

Symptoms of overdose include drowsiness (severe); shortness of breath or troubled breathing; unusual tiredness or weakness (severe).

Originator

Vontrol,SKF,US,1967

The Uses of Difenidol

Anti-emetic.

Background

Diphenidol is an antiemetic agent used in the treatment of vomiting and vertigo. Diphenidol overdose may result in serious toxicity in children.

Indications

For use in the prevention and symptomatic treatment of peripheral (labyrinthine) vertigo and associated nausea and vomiting that occur in such conditions as Meniere's disease and surgery of the middle and inner ear. Also for the control of nausea and vomiting associated with postoperative states, malignant neoplasms, labyrinthine disturbances, antineoplastic agent therapy, radiation sickness, and infectious diseases.

Definition

ChEBI: A tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4.

Manufacturing Process

2.6 grams magnesium, activated by means of iodine, is introduced into 20 cc of absolute ether and is caused to react with 0.6 cc of ethyl
omide. While warming gently, 16.2 grams (0.1 mol) of N-[1-chloropropyl-(3)]-piperidine in 40 cc of absolute ether are added and, after adding a further 0.5 cc of ethyl
omide, 14.5 grams (0.08 mol) of benzophenone in 50 cc of anhydrous ether are added in portions. The magnesium is used up fairly quickly and, after 10 hours, only traces are left. In working up, both with hydrochloric acid and with ammonium chloride, the hydrochloride of diphenyl-3-piperidinopropyl carbinol is precipitated as a dense precipitate. It is purified by recrystallization from chloroform-ethyl acetate. MP 212-214°C.

Therapeutic Function

Antinauseant

Trade name

Vontrol (Smith Kline & French), Cephadol (Nippon Shinyaku).

Pharmacokinetics

Diphenidol is used for control of nausea and vomiting. It has an antivertigo effect on the vestibular apparatus, inhibiting the chemoreceptor trigger zone to control nausea and vomiting, thus preventing motion sickness.

Metabolism

Not Available