Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C8H18N2O4S |
Molecular Weight | 238.305 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H](N)C(=O)NCCCS(O)(=O)=O
InChI
InChIKey=NRZRFNYKMSAZBI-ZETCQYMHSA-N
InChI=1S/C8H18N2O4S/c1-6(2)7(9)8(11)10-4-3-5-15(12,13)14/h6-7H,3-5,9H2,1-2H3,(H,10,11)(H,12,13,14)/t7-/m0/s1
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 |
---|---|---|---|
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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Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. | 2001 |
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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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Synthesis and characterization of N,N-dichlorinated amino acids: taurine, homotaurine, GABA and L-leucine. | 2001 Jun |
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Role of K+ -channels in homotaurine-induced analgesia. | 2001 Jun |
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Interactions between taurine and ethanol in the central nervous system. | 2002 |
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Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release. | 2002 Feb 15 |
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Effects of sulfur containing amino acids on iron and nitric oxide stimulated catecholamine oxidation. | 2002 Jun |
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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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Acamprosate: a new tool in the battle against alcohol dependence. | 2006 Dec |
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Diazepam inhibits the induction and maintenance of LTP of C-fiber evoked field potentials in spinal dorsal horn of rats. | 2006 Feb |
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Influence of a proton gradient on the transport kinetics of the H+/amino acid cotransporter PAT1 in Caco-2 cells. | 2006 Jul |
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Tramiprosate. | 2006 May |
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A Phase II study targeting amyloid-beta with 3APS in mild-to-moderate Alzheimer disease. | 2006 Nov 28 |
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Gateways to clinical trials. | 2006 Oct |
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A phase 2 study of tramiprosate for cerebral amyloid angiopathy. | 2006 Oct-Dec |
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The amyloid beta ion channel hypothesis of Alzheimer's disease. | 2007 |
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Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
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Pharmacogenetic aspects of addictive behaviors. | 2007 |
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Current therapeutic options for Alzheimer's disease. | 2007 Dec |
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Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions. | 2007 Dec |
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Therapies for Alzheimer's disease. | 2007 May |
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Influences of different developmental periods of taurine supplements on synaptic plasticity in hippocampal CA1 area of rats following prenatal and perinatal lead exposure. | 2007 May 19 |
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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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The effects of taurine, hypotaurine, and taurine homologs on erythrocyte morphology, membrane fluidity and cytoskeletal spectrin alterations due to diabetes, alcoholism and diabetes-alcoholism in the rat. | 2009 |
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The effects of taurine, taurine homologs and hypotaurine on cell and membrane antioxidative system alterations caused by type 2 diabetes in rat erythrocytes. | 2009 |
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Multivalent & multifunctional ligands to beta-amyloid. | 2009 |
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Lessons learned in the use of volumetric MRI in therapeutic trials in Alzheimer's disease: the ALZHEMED (Tramiprosate) experience. | 2009 Apr |
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Recent developments in Alzheimer's disease therapeutics. | 2009 Feb 19 |
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Alzheimer's disease therapeutic research: the path forward. | 2009 Jul 9 |
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Drug development for Alzheimer's disease: where are we now and where are we headed? | 2009 Jun |
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Effect of tramiprosate in patients with mild-to-moderate Alzheimer's disease: exploratory analyses of the MRI sub-group of the Alphase study. | 2009 Jun |
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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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Regulation of in vitro Aβ1-40 aggregation mediated by small molecules. | 2010 |
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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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Update on the pharmacological treatment of Alzheimer's disease. | 2010 Mar |
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The persisting burden of intracerebral haemorrhage: can effective treatments be found? | 2010 Oct 19 |
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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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GHG2B47067
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C186402
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1034190-08-3
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