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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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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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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Pharmacogenetic aspects of addictive behaviors. | 2007 |
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Targeting soluble Abeta peptide with Tramiprosate for the treatment of brain amyloidosis. | 2007 Apr |
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Tramiprosate, a drug of potential interest for the treatment of Alzheimer's disease, promotes an abnormal aggregation of tau. | 2007 Sep 6 |
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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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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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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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:11:44 GMT 2025
by
admin
on
Mon Mar 31 18:11:44 GMT 2025
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Record UNII |
5K8EAX0G53
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Record Status |
Validated (UNII)
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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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Related Record | Type | Details | ||
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TARGET->INHIBITOR OF AGGREGATION |
A? was maintained in a random-coil/?-helical rich conformation in the presence of Tramiprosate at a 20:1 ratio of Tramiprosate:A?. Binds and shows anti-fibrillogenic activity.
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TARGET->INHIBITOR OF AGGREGATION |
A? was maintained in a random-coil/?-helical rich conformation in the presence of Tramiprosate at a 20:1 ratio of Tramiprosate:A?. Binds and shows anti-fibrillogenic activity.
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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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