3-(acetylamino)propanesulphonic acid

Absorption

Acamprosate is absorbed in the gastrointestinal tract. The absolute bioavailability of acamprosate after oral administration is about 11%. The effect of food absorption is clinically insignificant and no adjustment of the dose is necessary with regard to meals. After repeated oral doses of 666 mg 3 times a day, steady-state concentrations are achieved within 5 to 7 days, with plasma concentration ranging between 370 to 650 micrograms/L.

Toxicity

The intraperitoneal LD50 in male mice is 1.87 g/kg. In reported cases of acute overdosage with acamprosate (doses of up to 56 grams of acamprosate calcium) diarrhea was the only reported symptom attributable to acamprosate. In the case of an overdose, supportive and symptomatic treatment is recommended.

Originator

Campral,Merck

The Uses of 3-(acetylamino)propanesulphonic acid

Treatment of alcohol dependency.

Background

Alcohol use disorder is responsible for a large worldwide burden of morbidity, premature mortality, and economic consequences resulting from accidents, violence, incarceration, decreased productivity, and increased healthcare spending.
Acamprosate, also known by the brand name Campral, is a drug used for the maintenance of alcohol abstinence. It is a structural analogue of the neurotransmitter γ-aminobutyric acid (GABA). Acamprosate is the first medication specifically formulated for the maintenance of alcohol abstinence in ethanol-dependent patients after alcohol detoxification, unlike naltrexone and disulfiram. It was first approved by the FDA in 2004 and initially marketed by Forest Laboratories.

Indications

Acamprosate is indicated for the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation. It is also indicated for the maintenance of alcohol abstinence in patients who have undergone alcohol detoxification. This drug should be used with a psychosocial support program providing adequate support.

Definition

ChEBI: An organosulfonic acid that is propane-1-sulfonic acid substituted by an acetylamino group at position 3.

Manufacturing Process

In a 4 liter flask provided with stirring means, a bromine funnel and a thermometer, 17.5% sodium hydroxide solution and aminopropanesulfonic acid (homotaurine) are added.
After complete dissolution, at a temperature of between 25°-40°C, acetic anhydride are added so as not to exceed a temperature of between 30°-40°C. The mixture is then maintained at this temperature by heating for at least 1 h.
The solution is then concentrated in vacuum, the residue is redissolved in 2.5 L of distilled water and the mixture is concentrated again. The residue is then dissolved in 1.6 L of distilled water, filtered, then concentrated almost completely. Drying is terminated in an oven in vacuum. A colorless crystalline powder of 3-acetylaminopropanesulfonate of sodium (sodium Nacetylhomotaurinate) is obtained.
The 3-acetylaminopropanesulfonic acid may be produced by treatment of 3- acetylaminopropanesulfonate of sodium with hydrochloric acid.
In practice it is usually used as calcium salt.

brand name

Campral (Forest).

Therapeutic Function

Psychotropic

Pharmacokinetics

Acamprosate acts on the CNS, aiding in the restoration of normal glutaminergic neuron activity. Pharmacodynamic studies have shown that acamprosate calcium reduces alcohol intake in alcohol-dependent individuals, likely through effects on NMDA receptors and calcium channels. It is a safe and well-tolerated drug for patients with alcohol dependency and improves the likelihood of alcohol abstinence.

Metabolism

Acamprosate is not metabolized.