U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of Tramiprosate

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)

HIDE SMILES / InChI

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.

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 18:11:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:44 GMT 2025
Record UNII
5K8EAX0G53
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-AMINOPROPANE SULFONIC ACID
INCI  
INCI  
Preferred Name English
Tramiprosate
INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
HOMOTAURINE
Common Name English
ACAMPROSATE CALCIUM IMPURITY A [EP IMPURITY]
Common Name English
ACAMPROSATE RELATED COMPOUND A [USP-RS]
Common Name English
1-PROPANESULFONIC ACID, 3-AMINO-
Systematic Name English
TRAMIPROSATE [USAN]
Common Name English
NC-531
Code English
tramiprosate [INN]
Common Name English
3-Aminopropane-1-sulfonic acid
Systematic Name English
TRAMIPROSATE [MI]
Common Name English
Tramiprosate [WHO-DD]
Common Name English
NSC-77071
Code English
3-AMINO-1-PROPANESULFONIC ACID
Systematic Name English
3-AMINOPROPANESULFONIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
DSLD 4321 (Number of products:1)
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
Code System Code Type Description
INN
8631
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PRIMARY
DRUG BANK
DB06527
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PRIMARY
RXCUI
1374845
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PRIMARY RxNorm
PUBCHEM
1646
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PRIMARY
DAILYMED
5K8EAX0G53
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PRIMARY
EPA CompTox
DTXSID80190352
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PRIMARY
RS_ITEM_NUM
1000565
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PRIMARY
NSC
77071
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PRIMARY
MERCK INDEX
m10998
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PRIMARY Merck Index
FDA UNII
5K8EAX0G53
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
PRIMARY
NCI_THESAURUS
C76786
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PRIMARY
CAS
3687-18-1
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PRIMARY
ChEMBL
CHEMBL149082
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PRIMARY
ECHA (EC/EINECS)
222-977-4
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PRIMARY
MESH
C001355
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
PRIMARY
WIKIPEDIA
HOMOTAURINE
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
PRIMARY
USAN
QQ-111
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PRIMARY
SMS_ID
100000090589
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
PRIMARY
EVMPD
SUB25707
Created by admin on Mon Mar 31 18:11:44 GMT 2025 , Edited by admin on Mon Mar 31 18:11:44 GMT 2025
PRIMARY
Related Record Type Details
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.
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.
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY