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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
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
Baclofen induces catatonia in rats.
1987 Sep
Treatment of alcohol-dependent outpatients with acamprosate: a clinical review.
2001
Taurine is a weak scavenger of peroxynitrite and does not attenuate sodium nitroprusside toxicity to cells in culture.
2001
Synthesis and characterization of N,N-dichlorinated amino acids: taurine, homotaurine, GABA and L-leucine.
2001 Jun
Role of K+ -channels in homotaurine-induced analgesia.
2001 Jun
Interactions between taurine and ethanol in the central nervous system.
2002
Effects of acute acamprosate and homotaurine on ethanol intake and ethanol-stimulated mesolimbic dopamine release.
2002 Feb 15
Effects of sulfur containing amino acids on iron and nitric oxide stimulated catecholamine oxidation.
2002 Jun
Interactions of taurine and structurally related analogues with the GABAergic system and taurine binding sites of rabbit brain.
2003 Mar
Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1.
2004 Apr
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
Inhibitors arrest myofibrillogenesis in skeletal muscle cells at early stages of assembly.
2004 Sep
The regulation of alpha-MSH release by GABA is mediated by a chloride-dependent [Ca2+]c increase in frog melanotrope cells.
2005 Oct
Acamprosate: a new tool in the battle against alcohol dependence.
2006 Dec
Diazepam inhibits the induction and maintenance of LTP of C-fiber evoked field potentials in spinal dorsal horn of rats.
2006 Feb
Influence of a proton gradient on the transport kinetics of the H+/amino acid cotransporter PAT1 in Caco-2 cells.
2006 Jul
Tramiprosate.
2006 May
A Phase II study targeting amyloid-beta with 3APS in mild-to-moderate Alzheimer disease.
2006 Nov 28
Gateways to clinical trials.
2006 Oct
A phase 2 study of tramiprosate for cerebral amyloid angiopathy.
2006 Oct-Dec
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
Current therapeutic options for Alzheimer's disease.
2007 Dec
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.
2007 Dec
Therapies for Alzheimer's disease.
2007 May
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
Present and prospective clinical therapeutic regimens for Alzheimer's disease.
2008 Aug
Preventing beta-amyloid fibrillization and deposition: beta-sheet breakers and pathological chaperone inhibitors.
2008 Dec 3
Assimilation of homotaurine-nitrogen by Burkholderia sp. and excretion of sulfopropanoate.
2008 Feb
[New approaches for the development of anti-Alzheimer's disease drugs based on the cholinergic hypothesis and amyloid hypothesis].
2008 May
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
Lessons learned in the use of volumetric MRI in therapeutic trials in Alzheimer's disease: the ALZHEMED (Tramiprosate) experience.
2009 Apr
Recent developments in Alzheimer's disease therapeutics.
2009 Feb 19
Alzheimer's disease therapeutic research: the path forward.
2009 Jul 9
Drug development for Alzheimer's disease: where are we now and where are we headed?
2009 Jun
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
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
Homotaurine: a failed drug for Alzheimer's disease and now a nutraceutical for memory protection.
2009 Nov 1
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
Reciprocal regulation between taurine and glutamate response via Ca2+-dependent pathways in retinal third-order neurons.
2010 Aug 24
Determination of the natural abundance δ15N of taurine by gas chromatography-isotope ratio measurement mass spectrometry.
2010 Dec 15
Glycine receptors in the nucleus accumbens involved in the ethanol intake-reducing effect of acamprosate.
2010 Jan
[Progress in the development of anti-amyloid drugs for treatment of Alzheimer's disease.].
2010 Jul
Update on the pharmacological treatment of Alzheimer's disease.
2010 Mar
The persisting burden of intracerebral haemorrhage: can effective treatments be found?
2010 Oct 19
Investigation of the noncovalent interactions between anti-amyloid agents and amyloid beta peptides by ESI-MS.
2010 Sep
Name Type Language
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
BLU-8499
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 Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
PRIMARY
FDA UNII
GHG2B47067
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
PRIMARY
SMS_ID
300000026231
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
PRIMARY
PUBCHEM
25008296
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
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NCI_THESAURUS
C186402
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
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CAS
1034190-08-3
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
PRIMARY
USAN
JK-46
Created by admin on Sat Dec 16 10:16:14 GMT 2023 , Edited by admin on Sat Dec 16 10:16:14 GMT 2023
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