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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
Baclofen induces catatonia in rats.
1987 Sep
Neurotoxic effect of acamprosate, n-acetyl-homotaurine, in cultured neurons.
2001 Jan-Feb
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
Molecule of the month. Tramiprosate.
2006 Jan-Feb
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
Substrate specificity of the amino acid transporter PAT1.
2006 Sep
The amyloid beta ion channel hypothesis of Alzheimer's disease.
2007
Progress update: Pharmacological treatment of Alzheimer's disease.
2007
Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon.
2007
Targeting soluble Abeta peptide with Tramiprosate for the treatment of brain amyloidosis.
2007 Apr
Anti-inflammatory and immune therapy for Alzheimer's disease: current status and future directions.
2007 Dec
Therapies for Alzheimer's disease.
2007 May
[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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:52:32 GMT 2023
Edited
by admin
on Fri Dec 15 15:52:32 GMT 2023
Record UNII
5K8EAX0G53
Record Status Validated (UNII)
Record Version
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Name Type Language
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
3-AMINOPROPANE SULFONIC ACID [INCI]
Common Name English
TRAMIPROSATE [USAN]
Common Name English
3-AMINOPROPANE SULFONIC ACID
INCI  
INCI  
Official Name 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 Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
DSLD 4321 (Number of products:1)
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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
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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 Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
WIKIPEDIA
HOMOTAURINE
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
USAN
QQ-111
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
SMS_ID
100000090589
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
EVMPD
SUB25707
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY