Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H9NO3S |
Molecular Weight | 139.173 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCS(O)(=O)=O
InChI
InChIKey=SNKZJIOFVMKAOJ-UHFFFAOYSA-N
InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)
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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Synthesis and characterization of N,N-dichlorinated amino acids: taurine, homotaurine, GABA and L-leucine. | 2001 Jun |
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Interactions between taurine and ethanol in the central nervous system. | 2002 |
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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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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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Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon. | 2007 |
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Present and prospective clinical therapeutic regimens for Alzheimer's disease. | 2008 Aug |
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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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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1509
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DSLD |
4321 (Number of products:1)
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8631
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DB06527
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1374845
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1646
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5K8EAX0G53
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DTXSID80190352
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1000565
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77071
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m10998
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5K8EAX0G53
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C76786
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3687-18-1
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CHEMBL149082
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222-977-4
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C001355
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HOMOTAURINE
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QQ-111
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100000090589
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SUB25707
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)