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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
Structure of VALILTRAMIPROSATE

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

HIDE SMILES / InChI

Molecular Formula C8H18N2O4S
Molecular Weight 238.305
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Determination of the natural abundance δ15N of taurine by gas chromatography-isotope ratio measurement mass spectrometry.
2010-12-15
The persisting burden of intracerebral haemorrhage: can effective treatments be found?
2010-10-19
Investigation of the noncovalent interactions between anti-amyloid agents and amyloid beta peptides by ESI-MS.
2010-09
Reciprocal regulation between taurine and glutamate response via Ca2+-dependent pathways in retinal third-order neurons.
2010-08-24
[Progress in the development of anti-amyloid drugs for treatment of Alzheimer's disease.].
2010-07
Update on the pharmacological treatment of Alzheimer's disease.
2010-03
Glycine receptors in the nucleus accumbens involved in the ethanol intake-reducing effect of acamprosate.
2010-01
Regulation of in vitro Aβ1-40 aggregation mediated by small molecules.
2010
Simple in vitro assays to identify amyloid-beta aggregation blockers for Alzheimer's disease therapy.
2010
Homotaurine: a failed drug for Alzheimer's disease and now a nutraceutical for memory protection.
2009-11-01
Domain-specific cognitive effects of tramiprosate in patients with mild to moderate Alzheimer's disease: ADAS-cog subscale results from the Alphase Study.
2009-11
Alzheimer's disease therapeutic research: the path forward.
2009-07-09
Drug development for Alzheimer's disease: where are we now and where are we headed?
2009-06
Effect of tramiprosate in patients with mild-to-moderate Alzheimer's disease: exploratory analyses of the MRI sub-group of the Alphase study.
2009-06
Lessons learned in the use of volumetric MRI in therapeutic trials in Alzheimer's disease: the ALZHEMED (Tramiprosate) experience.
2009-04
Recent developments in Alzheimer's disease therapeutics.
2009-02-19
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
The effects of taurine, taurine homologs and hypotaurine on cell and membrane antioxidative system alterations caused by type 2 diabetes in rat erythrocytes.
2009
Multivalent & multifunctional ligands to beta-amyloid.
2009
Preventing beta-amyloid fibrillization and deposition: beta-sheet breakers and pathological chaperone inhibitors.
2008-12-03
Present and prospective clinical therapeutic regimens for Alzheimer's disease.
2008-08
[New approaches for the development of anti-Alzheimer's disease drugs based on the cholinergic hypothesis and amyloid hypothesis].
2008-05
Assimilation of homotaurine-nitrogen by Burkholderia sp. and excretion of sulfopropanoate.
2008-02
Taurine, an inducer for tau polymerization and a weak inhibitor for amyloid-beta-peptide aggregation.
2007-12-18
Current therapeutic options for Alzheimer's disease.
2007-12
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.
2007-12
Tramiprosate, a drug of potential interest for the treatment of Alzheimer's disease, promotes an abnormal aggregation of tau.
2007-09-06
Influences of different developmental periods of taurine supplements on synaptic plasticity in hippocampal CA1 area of rats following prenatal and perinatal lead exposure.
2007-05-19
Therapies for Alzheimer's disease.
2007-05
Targeting soluble Abeta peptide with Tramiprosate for the treatment of brain amyloidosis.
2007-04
The amyloid beta ion channel hypothesis of Alzheimer's disease.
2007
Progress update: Pharmacological treatment of Alzheimer's disease.
2007
Pharmacogenetic aspects of addictive behaviors.
2007
Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon.
2007
Acamprosate: a new tool in the battle against alcohol dependence.
2006-12
A phase 2 study of tramiprosate for cerebral amyloid angiopathy.
2006-11-30
A Phase II study targeting amyloid-beta with 3APS in mild-to-moderate Alzheimer disease.
2006-11-28
Gateways to clinical trials.
2006-10
Substrate specificity of the amino acid transporter PAT1.
2006-09
Influence of a proton gradient on the transport kinetics of the H+/amino acid cotransporter PAT1 in Caco-2 cells.
2006-07
Tramiprosate.
2006-05
Molecule of the month. Tramiprosate.
2006-03-22
Diazepam inhibits the induction and maintenance of LTP of C-fiber evoked field potentials in spinal dorsal horn of rats.
2006-02
The regulation of alpha-MSH release by GABA is mediated by a chloride-dependent [Ca2+]c increase in frog melanotrope cells.
2005-10
Inhibitors arrest myofibrillogenesis in skeletal muscle cells at early stages of assembly.
2004-09
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.
2004-06
Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1.
2004-04
Interactions of taurine and structurally related analogues with the GABAergic system and taurine binding sites of rabbit brain.
2003-03
Interactions between taurine and ethanol in the central nervous system.
2002
Baclofen induces catatonia in rats.
1987-09
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:08:48 GMT 2025
Edited
by admin
on Mon Mar 31 23:08:48 GMT 2025
Record UNII
GHG2B47067
Record Status Validated (UNII)
Record Version
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Name Type Language
BLU-8499
Preferred Name English
VALILTRAMIPROSATE
USAN  
Official Name English
NRM-8499
Code English
3-((2S)-2-AMINO-3-METHYLBUTAMIDO)PROPANE-1-SULFONIC ACID
Systematic Name English
ALZ-801
Code English
BLU8499
Code English
NRM8499
Code English
valiltramiprosate [INN]
Common Name English
1-PROPANESULFONIC ACID, 3-(((2S)-2-AMINO-3-METHYL-1-OXOBUTYL)AMINO)-
Systematic Name English
VALILTRAMIPROSATE [USAN]
Common Name English
Code System Code Type Description
INN
11912
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
FDA UNII
GHG2B47067
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
SMS_ID
300000026231
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
PUBCHEM
25008296
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
NCI_THESAURUS
C186402
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
CAS
1034190-08-3
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
USAN
JK-46
Created by admin on Mon Mar 31 23:08:48 GMT 2025 , Edited by admin on Mon Mar 31 23:08:48 GMT 2025
PRIMARY
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