Acamprosate calcium
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MedKoo CAT#: 326701

CAS#: 77337-73-6 (calcium salt); 77337-76-9 (free acid).

Description: Acamprosate is a medication used along with counselling in the treatment of alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcohol withdrawal. Reports indicate that acamprosate works to best advantage in combination with psychosocial support and can help facilitate reduced consumption as well as full abstinence. Until it became a generic in the United States, Campral was manufactured and marketed in the United States by Forest Laboratories, while Merck KGaA markets it outside the US.


Chemical Structure

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Acamprosate calcium
CAS# 77337-73-6 (calcium salt); 77337-76-9 (free acid).

Theoretical Analysis

MedKoo Cat#: 326701
Name: Acamprosate calcium
CAS#: 77337-73-6 (calcium salt); 77337-76-9 (free acid).
Chemical Formula: C10H20CaN2O8S2
Exact Mass:
Molecular Weight: 400.474
Elemental Analysis: C, 29.99; H, 5.03; Ca, 10.01; N, 7.00; O, 31.96; S, 16.01

Price and Availability

Size Price Availability Quantity
100.0mg USD 175.0 2 Weeks
200.0mg USD 290.0 2 Weeks
500.0mg USD 515.0 2 Weeks
1.0g USD 750.0 2 Weeks
2.0g USD 1100.0 2 Weeks
5.0g USD 2015.0 2 Weeks
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Synonym: Alcomed; Aotal; Campral; Sobriol; Acamprosate calcium

IUPAC/Chemical Name: Calcium 3-(acetylamino)propane-1-sulfonate

InChi Key: BUVGWDNTAWHSKI-UHFFFAOYSA-L

InChi Code: InChI=1S/2C5H11NO4S.Ca/c2*1-5(7)6-3-2-4-11(8,9)10;/h2*2-4H2,1H3,(H,6,7)(H,8,9,10);/q;;+2/p-2

SMILES Code: O=S(CCCNC(C)=O)([O-])=O.O=S(CCCNC(C)=O)([O-])=O.[Ca+2]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Acamprosate calcium (Campral EC) is a GABA receptor agonist and modulator of glutamatergic systems.
In vitro activity: TBD
In vivo activity: This study next investigated whether acamprosate administration affected concentrations of vesicular glutamate and zinc in the hippocampus of intact brain. Immunohistochemical examination of the hippocampal dentate gyrus area showed expression of VGLUT1 or ZnT3 in the vehicle-treated group. In contrast, VGLUT1 or ZnT3 expression was significantly reduced in the acamprosate-treated group at the same hippocampal area (VGLUT1: vehicle, 30.74 ± 2.8; acamprosate, 19.36 ± 1.8, a 37% decrease; ZnT3: vehicle, 24.98 ± 1.25; acamprosate, 19.62 ± 0.36, a 21% decrease; average gray-scale intensities; Fig 1 B, C, F, and G). Western blot also revealed a significant decrease in the level of each of these proteins in the hippocampus of rats receiving acamprosate for 2 weeks as compared with the vehicle-treated group (VGLUT1: 0.48-fold change, P < 0.01; ZnT3: 0.74-fold change, P < 0.01; Fig 1 A–H). Moreover, the vesicular TSQ intensity was also significantly decreased in the hippocampal mossy fibers in rats receiving acamprosate as compared with the vehicle-treated group (vehicle, 24.3 ± 0.68; acamprosate, 19.68 ± 0.81, a 19% decrease; average gray-scale intensities; Fig 1 I–K). Reference: Transl Res. 2019 May;207:1-18. https://pubmed.ncbi.nlm.nih.gov/30731068/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.5 1.25
PBS (pH 7.2) 1.0 2.5
Water 50.0 124.85

Preparing Stock Solutions

The following data is based on the product molecular weight 400.474 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Choi BY, Lee SH, Choi HC, Lee SK, Yoon HS, Park JB, Chung WS, Suh SW. Alcohol dependence treating agent, acamprosate, prevents traumatic brain injury-induced neuron death through vesicular zinc depletion. Transl Res. 2019 May;207:1-18. doi: 10.1016/j.trsl.2019.01.002. Epub 2019 Jan 17. PMID: 30731068. 2. Chau P, Lidö HH, Söderpalm B, Ericson M. Acamprosate's ethanol intake-reducing effect is associated with its ability to increase dopamine. Pharmacol Biochem Behav. 2018 Dec;175:101-107. doi: 10.1016/j.pbb.2018.09.009. Epub 2018 Sep 26. PMID: 30266455.
In vitro protocol: TBD
In vivo protocol: 1. Choi BY, Lee SH, Choi HC, Lee SK, Yoon HS, Park JB, Chung WS, Suh SW. Alcohol dependence treating agent, acamprosate, prevents traumatic brain injury-induced neuron death through vesicular zinc depletion. Transl Res. 2019 May;207:1-18. doi: 10.1016/j.trsl.2019.01.002. Epub 2019 Jan 17. PMID: 30731068. 2. Chau P, Lidö HH, Söderpalm B, Ericson M. Acamprosate's ethanol intake-reducing effect is associated with its ability to increase dopamine. Pharmacol Biochem Behav. 2018 Dec;175:101-107. doi: 10.1016/j.pbb.2018.09.009. Epub 2018 Sep 26. PMID: 30266455.

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1: Ho AM, Qiu Y, Jia YF, Aguiar FS, Hinton DJ, Karpyak VM, Weinshilboum RM, Choi DS. Combined Effects of Acamprosate and Escitalopram on Ethanol Consumption in Mice. Alcohol Clin Exp Res. 2016 May 17. doi: 10.1111/acer.13099. [Epub ahead of print] PubMed PMID: 27184383.

2: Spanagel R, Vengeliene V, Kiefer F. Reply to: Does acamprosate really produce its anti-relapse effects via calcium? No support from the PREDICT study in human alcoholics. Neuropsychopharmacology. 2016 Feb;41(3):661-2. doi: 10.1038/npp.2015.263. PubMed PMID: 26742861; PubMed Central PMCID: PMC4707840.

3: Mann K, Hoffmann S, Pawlak CR. Does Acamprosate Really Produce its Anti-Relapse Effects via Calcium? No Support from the PREDICT Study in Human Alcoholics. Neuropsychopharmacology. 2016 Feb;41(3):659-60. doi: 10.1038/npp.2015.175. PubMed PMID: 26742860; PubMed Central PMCID: PMC4707814.

4: Knudsen HK, Roman PM. The Diffusion of Acamprosate for the Treatment of Alcohol Use Disorder: Results From a National Longitudinal Study. J Subst Abuse Treat. 2016 Mar;62:62-7. doi: 10.1016/j.jsat.2015.10.005. Epub 2015 Dec 1. PubMed PMID: 26689318; PubMed Central PMCID: PMC4724483.

5: Ewertowska M, Mikolajczak PL, Okulicz-Kozaryn I, Stacheck B, Murias M, Jodynis-Lieberti J. DIFFERENT RESPONSE OF ANTIOXIDANT DEFENSE SYSTEM TO ACAMPROSATE IN ETHANOL PREFERRING AND NON-PREFERRING RATS. Acta Pol Pharm. 2015 May-Jun;72(3):439-45. PubMed PMID: 26642652.

6: Hajj R, Milet A, Toulorge D, Cholet N, Laffaire J, Foucquier J, Robelet S, Mitry R, Guedj M, Nabirotchkin S, Chumakov I, Cohen D. Combination of acamprosate and baclofen as a promising therapeutic approach for Parkinson's disease. Sci Rep. 2015 Nov 6;5:16084. doi: 10.1038/srep16084. PubMed PMID: 26542636; PubMed Central PMCID: PMC4635348.

7: Luo Z, Shen Y, Liang M, Miao J, Mei Y, Wang Y, Qin Y. Pharmacokinetics and bioequivalence evaluation of acamprosate calcium tablets in healthy Chinese volunteers. Eur J Pharm Sci. 2015 Nov 15;79:67-72. doi: 10.1016/j.ejps.2015.09.003. Epub 2015 Sep 7. PubMed PMID: 26360834.

8: Nam HW, Karpyak VM, Hinton DJ, Geske JR, Ho AM, Prieto ML, Biernacka JM, Frye MA, Weinshilboum RM, Choi DS. Elevated baseline serum glutamate as a pharmacometabolomic biomarker for acamprosate treatment outcome in alcohol-dependent subjects. Transl Psychiatry. 2015 Aug 18;5:e621. doi: 10.1038/tp.2015.120. PubMed PMID: 26285131; PubMed Central PMCID: PMC4564571.

9: Doeppner TR, Pehlke JR, Kaltwasser B, Schlechter J, Kilic E, Bähr M, Hermann DM. The indirect NMDAR antagonist acamprosate induces postischemic neurologic recovery associated with sustained neuroprotection and neuroregeneration. J Cereb Blood Flow Metab. 2015 Dec;35(12):2089-97. doi: 10.1038/jcbfm.2015.179. Epub 2015 Jul 29. PubMed PMID: 26219600; PubMed Central PMCID: PMC4671132.

10: Long-term Use of Acamprosate Calcium for Alcoholism: A Review of the Clinical Effectiveness, Safety, and Guidelines [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 May 29. Available from http://www.ncbi.nlm.nih.gov/books/NBK304665/ PubMed PMID: 26180876.

11: Gueorguieva R, Wu R, Tsai WM, O'Connor PG, Fucito L, Zhang H, O'Malley SS. An analysis of moderators in the COMBINE study: Identifying subgroups of patients who benefit from acamprosate. Eur Neuropsychopharmacol. 2015 Oct;25(10):1586-99. doi: 10.1016/j.euroneuro.2015.06.006. Epub 2015 Jun 20. PubMed PMID: 26141511; PubMed Central PMCID: PMC4600651.

12: Plosker GL. Acamprosate: A Review of Its Use in Alcohol Dependence. Drugs. 2015 Jul;75(11):1255-68. doi: 10.1007/s40265-015-0423-9. Review. PubMed PMID: 26084940.

13: Hu W, Morris B, Carrasco A, Kroener S. Effects of acamprosate on attentional set-shifting and cellular function in the prefrontal cortex of chronic alcohol-exposed mice. Alcohol Clin Exp Res. 2015 Jun;39(6):953-61. doi: 10.1111/acer.12722. Epub 2015 Apr 23. PubMed PMID: 25903298.

14: Saitz R. [Acamprosate and naltrexone: similar efficacy for relapse]. Rev Med Suisse. 2014 Dec 17;10(455):2437. French. PubMed PMID: 25752019.

15: Mason BJ. Acamprosate, alcoholism, and abstinence. J Clin Psychiatry. 2015 Feb;76(2):e224-5. doi: 10.4088/JCP.14com09632. PubMed PMID: 25742214.

16: Higuchi S; Japanese Acamprosate Study Group. Efficacy of acamprosate for the treatment of alcohol dependence long after recovery from withdrawal syndrome: a randomized, double-blind, placebo-controlled study conducted in Japan (Sunrise Study). J Clin Psychiatry. 2015 Feb;76(2):181-8. doi: 10.4088/JCP.13m08940. PubMed PMID: 25742205.

17: Donoghue K, Elzerbi C, Saunders R, Whittington C, Pilling S, Drummond C. The efficacy of acamprosate and naltrexone in the treatment of alcohol dependence, Europe versus the rest of the world: a meta-analysis. Addiction. 2015 Jun;110(6):920-30. doi: 10.1111/add.12875. Epub 2015 Mar 17. PubMed PMID: 25664494.

18: Maremmani AG, Bacciardi S, Rovai L, Rugani F, Massimetti E, Gazzarrini D, Dell'Osso L, Maremmani I. Six-month outcome in bipolar spectrum alcoholics treated with acamprosate after detoxification: a retrospective study. Int J Environ Res Public Health. 2014 Dec;11(12):12983-96. PubMed PMID: 25590082.

19: Icro Maremmani AG, Bacciardi S, Rovai L, Rugani F, Massimetti E, Gazzarrini D, Dell'Osso L, Maremmani I. Six-month outcome in bipolar spectrum alcoholics treated with acamprosate after detoxification: a retrospective study. Int J Environ Res Public Health. 2014 Dec 12;11(12):12983-96. doi: 10.3390/ijerph111212983. PubMed PMID: 25514151; PubMed Central PMCID: PMC4276657.

20: Kraemer KL. Review: In alcohol use disorders, oral naltrexone, 50 mg/d, or acamprosate reduces return to drinking. Ann Intern Med. 2014 Oct 21;161(8):JC7. doi: 10.7326/0003-4819-161-8-201410210-02007. PubMed PMID: 25329224.