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Details

Stereochemistry ACHIRAL
Molecular Formula C3H6O6S2.2Na
Molecular Weight 248.186
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPRODISATE DISODIUM

SMILES

[Na+].[Na+].[O-]S(=O)(=O)CCCS([O-])(=O)=O

InChI

InChIKey=DKGJFKPIUSHDIT-UHFFFAOYSA-L
InChI=1S/C3H8O6S2.2Na/c4-10(5,6)2-1-3-11(7,8)9;;/h1-3H2,(H,4,5,6)(H,7,8,9);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C3H6O6S2
Molecular Weight 202.206
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Arresting amyloidosis in vivo using small-molecule anionic sulphonates or sulphates: implications for Alzheimer's disease.
1995 Feb
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
Diagnostic performance of amyloid A protein quantification in fat tissue of patients with clinical AA amyloidosis.
2007 Jun
Eprodisate for the treatment of renal disease in AA amyloidosis.
2007 Jun 7
Advances in the treatment of amyloidosis.
2007 Jun 7
Eprodisate for the treatment of renal disease in AA amyloidosis.
2007 Jun 7
[Multisystemic amyloidosis in 2007].
2007 May
Eprodisate slows the progression of renal disease in patients with AA amyloidosis.
2007 Nov
Eprodisate slows the progression of renal disease in patients with AA amyloidosis.
2007 Nov
Eprodisate in AA amyloidosis.
2007 Sep 13
Amyloid deposition in transplanted human pancreatic islets: a conceivable cause of their long-term failure.
2008
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
[Diagnostics and therapy of AA amyloidosis].
2009 May
[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
Review of eprodisate for the treatment of renal disease in AA amyloidosis.
2012
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:35:38 GMT 2023
Record UNII
5X0D9H16IU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPRODISATE DISODIUM
DASH   MART.   USAN  
USAN  
Official Name English
Eprodisate disodium [WHO-DD]
Common Name English
NC-503
Code English
KIACTA
Brand Name English
DISODIUM PROPANE-1,3-DISULPHONATE
Systematic Name English
EPRODISATE DISODIUM [MART.]
Common Name English
NSC-760403
Code English
Disodium propane-1,3-disulfonate
Systematic Name English
1,3-PROPANEDISULFONIC ACID, DISODIUM SALT
Common Name English
NSC-240395
Code English
EPRODISATE DISODIUM [USAN]
Common Name English
DISODIUM EPRODISATE
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/01/051
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
NCI_THESAURUS C45496
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9046732
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
FDA UNII
5X0D9H16IU
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
SMS_ID
100000089641
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
CAS
36589-58-9
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
NCI_THESAURUS
C65520
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
NSC
760403
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
PUBCHEM
6451143
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
USAN
QQ-107
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
EVMPD
SUB25381
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL2111092
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
NSC
240395
Created by admin on Fri Dec 15 16:35:38 GMT 2023 , Edited by admin on Fri Dec 15 16:35:38 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY