Acamprosate calcium | 77337-73-6 | 77337-76-9

MedKoo Cat#: 326701 | Name: Acamprosate calcium

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Description:

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

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

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: 0.0000

Molecular Weight: 400.47

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
250mg	USD 285.00	2 Weeks
1g	USD 650.00	2 Weeks

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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

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.5	1.25
	PBS (pH 7.2)	1.0	2.50
	Water	50.0	124.85

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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: 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.