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
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
Synthesis and characterization of N,N-dichlorinated amino acids: taurine, homotaurine, GABA and L-leucine.
2001 Jun
Interactions between taurine and ethanol in the central nervous system.
2002
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
The regulation of alpha-MSH release by GABA is mediated by a chloride-dependent [Ca2+]c increase in frog melanotrope cells.
2005 Oct
Gateways to clinical trials.
2006 Oct
Changing the course of Alzheimer's disease: anti-amyloid disease-modifying treatments on the horizon.
2007
Present and prospective clinical therapeutic regimens for Alzheimer's disease.
2008 Aug
[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
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)
Created by admin on Fri Dec 15 15:52:32 GMT 2023 , Edited by admin on Fri Dec 15 15:52:32 GMT 2023
Code System Code Type Description
INN
8631
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
DRUG BANK
DB06527
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
RXCUI
1374845
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 RxNorm
PUBCHEM
1646
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
DAILYMED
5K8EAX0G53
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
EPA CompTox
DTXSID80190352
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
RS_ITEM_NUM
1000565
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
NSC
77071
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
MERCK INDEX
m10998
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 Merck Index
FDA UNII
5K8EAX0G53
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
NCI_THESAURUS
C76786
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
CAS
3687-18-1
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
ChEMBL
CHEMBL149082
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
ECHA (EC/EINECS)
222-977-4
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
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