Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H8NO3S.Na |
Molecular Weight | 161.155 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].NCCCS([O-])(=O)=O
InChI
InChIKey=KMGJRCNLDZGSFX-UHFFFAOYSA-M
InChI=1S/C3H9NO3S.Na/c4-2-1-3-8(5,6)7;/h1-4H2,(H,5,6,7);/q;+1/p-1
Tramiprosate is a glycosaminoglycan mimetic designed to interfere with the actions of beta-amyloid peptides (Abeta) early in the cascade of amyloidogenic events. It is a patented variant of the amino acid taurine, which is reported to inhibit the interaction of Abeta with endogenous glycosaminoglycans and thereby prevent beta-sheet formation. Preclinical data have shown that tramiprosate reduces brain and plasma levels of Abeta, prevents fibril formation and exerts cytoprotective effects in the brain. The pharmacological effects have also been demonstrated in clinical trials of patients with mild to moderate Alzheimer's disease. Promising findings for the efficacy of tramiprosate, indicated by improvement or stabilization of cognitive function, have been shown in phase II clinical trials and open-label extensions of these studies. Furthermore, tramiprosate appears to be well tolerated with no reports of safety concerns. Tramiprosate is in phase III clinical trial for the treatment of Alzheimer's disease.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2487 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23484434 |
100.0 µM [IC50] | ||
Target ID: GO:0050435 |
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Target ID: CHEMBL2111463 |
PubMed
Title | Date | PubMed |
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Baclofen induces catatonia in rats. | 1987 Sep |
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Taurine is a weak scavenger of peroxynitrite and does not attenuate sodium nitroprusside toxicity to cells in culture. | 2001 |
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Interactions between taurine and ethanol in the central nervous system. | 2002 |
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Interactions of taurine and structurally related analogues with the GABAergic system and taurine binding sites of rabbit brain. | 2003 Mar |
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Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. | 2004 Apr |
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Taurine-induced long-lasting potentiation in the rat hippocampus shows a partial dissociation from total hippocampal taurine content and independence from activation of known taurine transporters. | 2004 Jun |
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Inhibitors arrest myofibrillogenesis in skeletal muscle cells at early stages of assembly. | 2004 Sep |
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The regulation of alpha-MSH release by GABA is mediated by a chloride-dependent [Ca2+]c increase in frog melanotrope cells. | 2005 Oct |
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Gateways to clinical trials. | 2006 Oct |
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Substrate specificity of the amino acid transporter PAT1. | 2006 Sep |
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Pharmacogenetic aspects of addictive behaviors. | 2007 |
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Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon. | 2007 |
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Taurine, an inducer for tau polymerization and a weak inhibitor for amyloid-beta-peptide aggregation. | 2007 Dec 18 |
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Present and prospective clinical therapeutic regimens for Alzheimer's disease. | 2008 Aug |
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Preventing beta-amyloid fibrillization and deposition: beta-sheet breakers and pathological chaperone inhibitors. | 2008 Dec 3 |
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Assimilation of homotaurine-nitrogen by Burkholderia sp. and excretion of sulfopropanoate. | 2008 Feb |
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[New approaches for the development of anti-Alzheimer's disease drugs based on the cholinergic hypothesis and amyloid hypothesis]. | 2008 May |
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Multivalent & multifunctional ligands to beta-amyloid. | 2009 |
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Recent developments in Alzheimer's disease therapeutics. | 2009 Feb 19 |
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Domain-specific cognitive effects of tramiprosate in patients with mild to moderate Alzheimer's disease: ADAS-cog subscale results from the Alphase Study. | 2009 Nov |
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Homotaurine: a failed drug for Alzheimer's disease and now a nutraceutical for memory protection. | 2009 Nov 1 |
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Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy. | 2010 |
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Reciprocal regulation between taurine and glutamate response via Ca2+-dependent pathways in retinal third-order neurons. | 2010 Aug 24 |
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Determination of the natural abundance δ15N of taurine by gas chromatography-isotope ratio measurement mass spectrometry. | 2010 Dec 15 |
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Glycine receptors in the nucleus accumbens involved in the ethanol intake-reducing effect of acamprosate. | 2010 Jan |
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[Progress in the development of anti-amyloid drugs for treatment of Alzheimer's disease.]. | 2010 Jul |
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Investigation of the noncovalent interactions between anti-amyloid agents and amyloid beta peptides by ESI-MS. | 2010 Sep |
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NCI_THESAURUS |
C1509
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m10998
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23663660
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238-700-5
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C132049
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD