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77337-76-9 molecular structure
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3-acetamidopropane-1-sulfonic acid

ChemBase ID: 541
Molecular Formular: C5H11NO4S
Molecular Mass: 181.21014
Monoisotopic Mass: 181.04087884
SMILES and InChIs

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

Cite this record

CBID:541 http://www.chembase.cn/molecule-541.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
77337-76-9
PubChem SID
46506657
160964004
PubChem CID
71158

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00659 external link
PubChem 71158 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa -1.1448904  H Acceptors
H Donor LogD (pH = 5.5) -4.1027274 
LogD (pH = 7.4) -4.1027603  Log P -2.8292274 
Molar Refractivity 38.9143 cm3 Polarizability 15.96749 Å3
Polar Surface Area 83.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.79  LOG S -0.98 
Solubility (Water) 1.88e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
-1.1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00659 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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