Acamprosate calcium Chemical Properties

Melting point:

>300°C

storage temp. 

2-8°C

solubility 

H2O: >5mg/mL

form 

powder

color 

White to Off-White

Water Solubility 

Soluble in water (100mM)

Merck 

14,17

CAS DataBase Reference

77337-73-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36

WGK Germany 

3

RTECS 

TZ6357000

HS Code 

29241990

Toxicity

LD50 i.p. in male mice: 1.87 g/kg (Durlach, 1982)

Acamprosate calcium Usage And Synthesis

Description

Acamprosate is an acetylated derivative of the GABA analog homotaurine (tramiprosate; ). Despite its structural similarity to GABA, acamprosate does not act at GABA_A receptors but does decrease paired-pulse inhibition of GABA_A inhibitory post-synaptic currents (IPSCs) at short inter-stimulus intervals when used at a concentration of 300 μM, indicating that it may inhibit GABA_B autoreceptor-mediated inhibition of GABA release. It is an NMDA receptor modulator with antagonist or agonist effects depending on brain region, receptor subunit composition, and other factors. Acamprosate (0.26 and 0.52 mmol/kg per day, i.p.) reduces voluntary intake of ethanol in rats, an effect that can be blocked by the GABA antagonist bicuculline . Formulations containing acamprosate have been used for the maintenance of alcohol abstinence.

Chemical Properties

Acamprosate calcium is White Crystalline Solid

Originator

Campral,Merck

Uses

Of interest for the treatment of alcoholism. Store at -20°C

Uses

glucocortcoid, antiinflammatory

Uses

Acamprosate calcium is a synthetic amino acid and a neurotransmitter analogue that is used as an alcohol deterrent in management of alcohol dependence and abuse. Acamprosate calcium was approved for use in the therapy of alcohol dependence and abuse in the United States in 2004.

Uses

Of interest for the treatment of alcoholism and other neurochemical disorders.

Definition

ChEBI: Acamprosate calcium is an organic calcium salt. It contains an acamprosate(1-).

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

Biological Activity

GABA receptor agonist and modulator of glutamatergic systems. Reduces alcohol consumption in animal models of alcohol addiction.

Biochem/physiol Actions

Acamprosate calcium is a GABA γ-aminobutyric acid agonist.

Clinical Use

Maintenance of abstinence in alcohol dependence

Metabolism

Acamprosate is excreted in the urine and is not metabolised significantly.

storage

Room temperature (desiccate)

References

1. wilde m i, wagstaff a j. acamprosate. drugs, 1997, 53(6): 1038-1053.

Acamprosate calcium(77337-73-6)Related Product Information

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