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)
Molecular Formula | C3H9NO3S |
Molecular Weight | 139.173 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Neurotoxic effect of acamprosate, n-acetyl-homotaurine, in cultured neurons. | 2001 Jan-Feb |
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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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Molecule of the month. Tramiprosate. | 2006 Jan-Feb |
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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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Substrate specificity of the amino acid transporter PAT1. | 2006 Sep |
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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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Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon. | 2007 |
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Targeting soluble Abeta peptide with Tramiprosate for the treatment of brain amyloidosis. | 2007 Apr |
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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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[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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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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:52:32 GMT 2023
by
admin
on
Fri Dec 15 15:52:32 GMT 2023
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Record UNII |
5K8EAX0G53
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Record Status |
Validated (UNII)
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Record Version |
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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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SALT/SOLVATE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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