| Identification | More | [Name]
Acamprosate calcium | [CAS]
77337-73-6 | [Synonyms]
3-(ACETYLAMINO)-1-PROPANESULFONIC ACID CALCIUM SALT
ACAMPROSATE CALCIUM
ACAMPROSATE CALCIUMSALT
calcium 3-acetamidopropane-1-sulfonate
calcium 3-(acetylamino)propanesulphonate
CALCIUM ACETYLHOMOTAURINE
calcium(2+) 3-(acetylamino)propanesulphonate
3-(Acetylamino)-1-propanesulfonic Acid Calcium Salt, Calcium Acetylhomotaurine
ALAMPROSATECALCIUM
3-(Acetylamino)-1-propanesulfonic acid calcium salt (2:1)
Bis[3-(acetylamino)-1-propanesulfonic acid]calcium salt
CaAOTA
Calcium acetylhomotaurinate | [EINECS(EC#)]
278-665-3 | [Molecular Formula]
C10H20CaN2O8S2 | [MDL Number]
MFCD00886588 | [Molecular Weight]
400.48 | [MOL File]
77337-73-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
>300°C | [storage temp. ]
Room temp | [solubility ]
H2O: >5mg/mL | [form ]
powder | [color ]
White to Off-White | [Water Solubility ]
Soluble in water (100mM) | [Usage]
Of interest for the treatment of alcoholism. Store at-20°C | [Merck ]
14,17 | [CAS DataBase Reference]
77337-73-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [RTECS ]
TZ6357000 | [HS Code ]
29241990 | [Toxicity]
LD50 i.p. in male mice: 1.87 g/kg (Durlach, 1982) |
| Hazard Information | Back Directory | [Description]
Acamprosate is an acetylated derivative of the GABA analog homotaurine (tramiprosate; Item No. 20701).1 Despite its structural similarity to GABA, acamprosate does not act at GABAA receptors but does decrease paired-pulse inhibition of GABAA inhibitory post-synaptic currents (IPSCs) at short inter-stimulus intervals when used at a concentration of 300 μM, indicating that it may inhibit GABAB autoreceptor-mediated inhibition of GABA release.2,3,4 It is an NMDA receptor modulator with antagonist or agonist effects depending on brain region, receptor subunit composition, and other factors.4 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 (Item No. 11727). Formulations containing acamprosate have been used for the maintenance of alcohol abstinence. | [Chemical Properties]
Acamprosate calcium is White Crystalline Solid
| [Originator]
Campral,Merck | [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]
glucocortcoid, antiinflammatory | [Uses]
Of interest for the treatment of alcoholism and other neurochemical disorders. | [Uses]
Of interest for the treatment of alcoholism. Store at -20°C | [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 | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [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. |
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