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Details

Stereochemistry ACHIRAL
Molecular Formula C3H8O6S2
Molecular Weight 204.222
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPRODISATE

SMILES

OS(=O)(=O)CCCS(O)(=O)=O

InChI

InChIKey=MGNVWUDMMXZUDI-UHFFFAOYSA-N
InChI=1S/C3H8O6S2/c4-10(5,6)2-1-3-11(7,8)9/h1-3H2,(H,4,5,6)(H,7,8,9)

HIDE SMILES / InChI
Eprodisate (1,3-propanedisulfonate) is a negatively charged, sulfonated molecule of low molecular weight that has structural similarities to heparin sulfate; it is a glycosaminoglycan mimetic that binds to the glycosaminoglycan (GAG) binding site on serum A amyloid (AA) to prevent its interaction with glycosaminoglycan and arrest amyloidosis, or inhibit amyloid deposition. In nonclinical toxicity studies in two animal species (i.e., rat and dog), eprodisate was administered orally at doses of up to 2000 mg/kg/day for 39 weeks: eprodisate showed low toxicity potential at doses several fold higher than the anticipated clinical dose, was well tolerated upon chronic exposure and was found to be nonmutagenic and nonclastogenic. Furthermore, a series of safety pharmacology studies showed that eprodisate does not have any clinically significant effect on major organ function.

Originator

Curator's Comment: Eprodisate (KIACTA™) was originally developed by BELLUS Health (http://www.bellushealth.com/English/home/default.aspx). In April 2008, Neurochem was renamed as BELLUS Health.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: 111345.0
Gene Symbol: Saa
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Ethanedisulfonate is degraded via sulfoacetaldehyde in Ralstonia sp. strain EDS1.
2001 Jul
Nordihydroguaiaretic acid potently breaks down pre-formed Alzheimer's beta-amyloid fibrils in vitro.
2002 May
Dissimilation of C3-sulfonates.
2006 Mar
Advances in the treatment of amyloidosis.
2007 Jun 7
[Multisystemic amyloidosis in 2007].
2007 May
Eprodisate in amyloid A amyloidosis: a novel therapeutic approach?
2008 Aug
Eprodisate in amyloid A amyloidosis: a novel therapeutic approach?
2008 Aug
Preventing beta-amyloid fibrillization and deposition: beta-sheet breakers and pathological chaperone inhibitors.
2008 Dec 3
[A new treatment of renal disease in AA amyloidosis...and not only that?].
2008 Jan-Feb
[Amyloidosis in rheumatic diseases].
2010
Two cationic metal-organic frameworks based on cadmium and α,ω-alkanedisulfonate anions and their photoluminescent properties.
2010 Dec 14
Systemic AA amyloidosis: epidemiology, diagnosis, and management.
2014
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Animals recieved amyloid enhancing factor (AEF) and an inflammatory stimulus to initiate amyloid development. In the acute model, animals were treated with the test compaund 24 hours after induction, and for the next five days. After the sixth days they were killed and their spleens were assessed for amyloid. Eprodisate sodium (Sodium 1,3-propanedisulphonate) was effective in this model (35+/-6% of amyloid found in the untreated controls). This inhibition of steroidogenesis is not a result of a reduction of hepatic serum A amyloid (SAA).
Swiss white mice 25-30 g; 50 mM in 7-8 ml of drinking water per animal per day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
EPRODISATE
INN  
INN  
Official Name English
PROPANE-1,3-DISULPHONATE
Systematic Name English
eprodisate [INN]
Common Name English
PROPANE-1,3-DISULFONATE
Systematic Name English
PROPANE-1,3-DISULFONIC ACID
Systematic Name English
1,3-PROPANEDISULFONIC ACID
Systematic Name English
Eprodisate [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 118998
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
Code System Code Type Description
PUBCHEM
428573
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PRIMARY
DRUG BANK
DB06405
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EPA CompTox
DTXSID4048301
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CAS
21668-77-9
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
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MESH
C520274
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SMS_ID
100000178030
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NCI_THESAURUS
C166957
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WIKIPEDIA
1,3-Propanedisulfonic acid
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
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FDA UNII
6QFP76V7S7
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
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ChEMBL
CHEMBL2111092
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INN
8630
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