Acamprosate calcium
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326701

CAS#: 77337-73-6 (calcium salt)

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

img
Acamprosate calcium
CAS# 77337-73-6 (calcium salt)

Theoretical Analysis

MedKoo Cat#: 326701
Name: Acamprosate calcium
CAS#: 77337-73-6 (calcium salt)
Chemical Formula: C10H20CaN2O8S2
Exact Mass: 0.00
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
100mg USD 350 2 Weeks
200mg USD 550 2 Weeks
500mg USD 1050 2 Weeks
1g USD 1650 2 Weeks
Bulk inquiry

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

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

More Info:

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 2.50
Water 50.0 124.85

Preparing Stock Solutions

The following data is based on the product molecular weight 400.47 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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Rösner S, Hackl-Herrwerth A, Leucht S, Lehert P, Vecchi S, Soyka M. Acamprosate for alcohol dependence. Cochrane Database Syst Rev. 2010 Sep 8;(9):CD004332. doi: 10.1002/14651858.CD004332.pub2. PMID: 20824837.


2: Ademar K, Adermark L, Söderpalm B, Ericson M. Sodium acamprosate and calcium exert additive effects on nucleus accumbens dopamine in the rat. Addict Biol. 2022 Sep;27(5):e13224. doi: 10.1111/adb.13224. PMID: 36001425; PMCID: PMC9541434.


3: Kranzler HR, Soyka M. Diagnosis and Pharmacotherapy of Alcohol Use Disorder: A Review. JAMA. 2018 Aug 28;320(8):815-824. doi: 10.1001/jama.2018.11406. PMID: 30167705; PMCID: PMC7391072.


4: Burnette EM, Nieto SJ, Grodin EN, Meredith LR, Hurley B, Miotto K, Gillis AJ, Ray LA. Novel Agents for the Pharmacological Treatment of Alcohol Use Disorder. Drugs. 2022 Feb;82(3):251-274. doi: 10.1007/s40265-021-01670-3. Epub 2022 Feb 8. PMID: 35133639; PMCID: PMC8888464.


5: Fairbanks J, Umbreit A, Kolla BP, Karpyak VM, Schneekloth TD, Loukianova LL, Sinha S. Evidence-Based Pharmacotherapies for Alcohol Use Disorder: Clinical Pearls. Mayo Clin Proc. 2020 Sep;95(9):1964-1977. doi: 10.1016/j.mayocp.2020.01.030. Epub 2020 May 20. PMID: 32446635.


6: Palpacuer C, Duprez R, Huneau A, Locher C, Boussageon R, Laviolle B, Naudet F. Pharmacologically controlled drinking in the treatment of alcohol dependence or alcohol use disorders: a systematic review with direct and network meta- analyses on nalmefene, naltrexone, acamprosate, baclofen and topiramate. Addiction. 2018 Feb;113(2):220-237. doi: 10.1111/add.13974. Epub 2017 Sep 20. PMID: 28940866.


7: Kennedy WK, Leloux M, Kutscher EC, Price PL, Morstad AE, Carnahan RM. Acamprosate. Expert Opin Drug Metab Toxicol. 2010 Mar;6(3):363-80. doi: 10.1517/17425251003641975. PMID: 20163323.


8: Maisel NC, Blodgett JC, Wilbourne PL, Humphreys K, Finney JW. Meta-analysis of naltrexone and acamprosate for treating alcohol use disorders: when are these medications most helpful? Addiction. 2013 Feb;108(2):275-93. doi: 10.1111/j.1360-0443.2012.04054.x. Epub 2012 Oct 17. PMID: 23075288; PMCID: PMC3970823.


9: 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. PMID: 26180876.


10: Pradhan G, Melugin PR, Wu F, Fang HM, Weber R, Kroener S. Calcium chloride mimics the effects of acamprosate on cognitive deficits in chronic alcohol- exposed mice. Psychopharmacology (Berl). 2018 Jul;235(7):2027-2040. doi: 10.1007/s00213-018-4900-1. Epub 2018 Apr 20. PMID: 29679288.


11: Patel AK, Balasanova AA. Treatment of Alcohol Use Disorder. JAMA. 2021 Feb 9;325(6):596. doi: 10.1001/jama.2020.2012. PMID: 33560323.


12: Spanagel R, Vengeliene V, Jandeleit B, Fischer WN, Grindstaff K, Zhang X, Gallop MA, Krstew EV, Lawrence AJ, Kiefer F. Acamprosate produces its anti- relapse effects via calcium. Neuropsychopharmacology. 2014 Mar;39(4):783-91. doi: 10.1038/npp.2013.264. Epub 2013 Sep 30. PMID: 24081303; PMCID: PMC3924515.


13: Schwartz TL, Siddiqui UA, Raza S, Costello A. Acamprosate calcium as augmentation therapy for anxiety disorders. Ann Pharmacother. 2010 Dec;44(12):1930-2. doi: 10.1345/aph.1P353. Epub 2010 Nov 9. PMID: 21062908.


14: Mason BJ, Heyser CJ. Alcohol Use Disorder: The Role of Medication in Recovery. Alcohol Res. 2021 Jun 3;41(1):07. doi: 10.35946/arcr.v41.1.07. PMID: 34113531; PMCID: PMC8184096.


15: Kufahl PR, Watterson LR, Olive MF. The development of acamprosate as a treatment against alcohol relapse. Expert Opin Drug Discov. 2014 Nov;9(11):1355-69. doi: 10.1517/17460441.2014.960840. Epub 2014 Sep 26. PMID: 25258174; PMCID: PMC4578640.


16: Anton RF, O'Malley SS, Ciraulo DA, Cisler RA, Couper D, Donovan DM, Gastfriend DR, Hosking JD, Johnson BA, LoCastro JS, Longabaugh R, Mason BJ, Mattson ME, Miller WR, Pettinati HM, Randall CL, Swift R, Weiss RD, Williams LD, Zweben A; COMBINE Study Research Group. Combined pharmacotherapies and behavioral interventions for alcohol dependence: the COMBINE study: a randomized controlled trial. JAMA. 2006 May 3;295(17):2003-17. doi: 10.1001/jama.295.17.2003. PMID: 16670409.


17: Naguy A, Alenezi S, Alwetayan S. Acamprosate for Treatment-Refractory Catatonia. Am J Ther. 2020 May/Jun;27(3):e324-e326. doi: 10.1097/MJT.0000000000000991. PMID: 31356347.


18: 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. PMID: 26084940.


19: Melugin PR, Wu F, Munoz C, Phensy A, Pradhan G, Luo Y, Nofal A, Manepalli R, Kroener S. The effects of acamprosate on prefrontal cortical function are mimicked by CaCl2 and they are influenced by the history of alcohol exposure. Neuropharmacology. 2022 Jul 1;212:109062. doi: 10.1016/j.neuropharm.2022.109062. Epub 2022 Apr 14. PMID: 35430241.


20: Bahji A, Bach P, Danilewitz M, Crockford D, Devoe DJ, El-Guebaly N, Saitz R. Pharmacotherapies for Adults With Alcohol Use Disorders: A Systematic Review and Network Meta-analysis. J Addict Med. 2022 Nov-Dec 01;16(6):630-638. doi: 10.1097/ADM.0000000000000992. PMID: 35653782; PMCID: PMC10010623.