3-acetamidopropane-1-sulfonic acid

• ChemBase ID: 541
• Molecular Formular: C5H11NO4S
• Molecular Mass: 181.21014
• Monoisotopic Mass: 181.04087884
• SMILES: S(=O)(=O)(O)CCCNC(=O)C
• Canonical SMILES: CC(=O)NCCCS(=O)(=O)O
• InChI: InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
• InChIKey: AFCGFAGUEYAMAO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetamidopropane-1-sulfonic acid
• IUPAC Traditional name: acamprosate
• Brand Name: Campral
• Synonyms: N-Acetylhomotaurine; 3-(Acetylamino)propanesulphonic acid; 3-Acetamido-1-propanesulfonic acid; acamprosate; Acamprosate

Database IDs

• CAS Number: 77337-76-9
• PubChem SID: 160964004; 46506657
• PubChem CID: 71158

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.1448904
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -4.1027274
• LogD (pH = 7.4): -4.1027603
• Log P: -2.8292274
• Molar Refractivity: 38.9143 cm^3
• Polarizability: 15.96749 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.79
• LOG S: -0.98
• Solubility (Water): 1.88e+01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.1

DETAILS

DrugBank - DB00659

• Drug Groups: approved; investigational
• Description: Acamprosate, also known by the brand name Campral™, is a drug used for treating alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcoholism, possibly by blocking glutaminergic N-methyl-D-aspartate receptors, while gamma-aminobutyric acid type A receptors are activated. Reports indicate that acamprosate only works with a combination of attending support groups and abstinence from alcohol. Certain serious side effects include allergic reactions, irregular heartbeats, and low or high blood pressure, while less serious side effects include headaches, insomnia, and impotence. Acamprosate should not be taken by people with kidney problems or allergies to the drug.
• Indication: For the maintenance of abstinence from alcohol in patients with alcohol dependence who are abstinent at treatment initiation
• Pharmacology: Pharmacodynamic studies have shown that acamprosate calcium reduces alcohol intake in alcohol-dependent animals in a dose-dependent manner and that this effect appears to be specific to alcohol and the mechanisms of alcohol dependence. Acamprosate calcium has negligible observable central nervous system (CNS) activity in animals outside of its effects on alcohol dependence, exhibiting no anticonvulsant, antidepressant, or anxiolytic activity.
• Toxicity: In all reported cases of acute overdosage with acamprosate (total reported doses of up to 56 grams of acamprosate calcium), the only symptom that could be reasonably associated with acamprosate was diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Acamprosate does not undergo metabolism.
• Absorption: The absolute bioavailability of acamprosate after oral administration is about 11%. The food effect on absorption is not clinically significant and no adjustment of dose is necessary.
• Half Life: 20 - 33 hours
• Protein Binding: Non detectable
• Elimination: Following oral administration of CAMPRAL?, the major route of excretion is via the kidneys as acamprosate.
• Distribution: * 72 to 109 L
• References: Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [Pubmed] ; Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. [Pubmed] ; Mason BJ, Goodman AM, Chabac S, Lehert P: Effect of oral acamprosate on abstinence in patients with alcohol dependence in a double-blind, placebo-controlled trial: the role of patient motivation. J Psychiatr Res. 2006 Aug;40(5):383-93. Epub 2006 Mar 20. [Pubmed] ; Feeney GF, Connor JP, Young RM, Tucker J, McPherson A: Combined acamprosate and naltrexone, with cognitive behavioural therapy is superior to either medication alone for alcohol abstinence: a single centres' experience with pharmacotherapy. Alcohol Alcohol. 2006 May-Jun;41(3):321-7. Epub 2006 Feb 8. [Pubmed] ; Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. Pubmed
• Feeney GF, Connor JP, Young RM, Tucker J, McPherson A: Combined acamprosate and naltrexone, with cognitive behavioural therapy is superior to either medication alone for alcohol abstinence: a single centres' experience with pharmacotherapy. Alcohol Alcohol. 2006 May-Jun;41(3):321-7. Epub 2006 Feb 8. Pubmed
• Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. Pubmed
• Mason BJ, Goodman AM, Chabac S, Lehert P: Effect of oral acamprosate on abstinence in patients with alcohol dependence in a double-blind, placebo-controlled trial: the role of patient motivation. J Psychiatr Res. 2006 Aug;40(5):383-93. Epub 2006 Mar 20. Pubmed
• Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. Pubmed