3-acetamidopropane-1-sulfonic acid

• ChemBase编号: 541
• 分子式: C5H11NO4S
• 平均质量: 181.21014
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-acetamidopropane-1-sulfonic acid
• IUPAC传统名: acamprosate
• 商标名: Campral
• 别名: N-Acetylhomotaurine; 3-(Acetylamino)propanesulphonic acid; 3-Acetamido-1-propanesulfonic acid; acamprosate; Acamprosate

登记号

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

理论计算性质

JChem

• Acid pKa: -1.1448904
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -4.1027274
• LogD (pH = 7.4): -4.1027603
• Log P: -2.8292274
• 摩尔折射率: 38.9143 cm^3
• 极化性: 15.96749 Å^3
• 极化表面积: 83.47 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.79
• LOG S: -0.98
• 溶解度: 1.88e+01 g/l

分子性质

理化性质

• 疏水性(logP): -1.1

详细说明

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

参考文献

• 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