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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

Molecular Formula C3H8O6S2
Molecular Weight 204.222
Charge 0
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
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
Eprodisate for the treatment of renal disease in AA amyloidosis.
2007 Jun 7
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
[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
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 16:11:16 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:16 GMT 2023
Record UNII
6QFP76V7S7
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
DRUG BANK
DB06405
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048301
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
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
PRIMARY
MESH
C520274
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
SMS_ID
100000178030
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
NCI_THESAURUS
C166957
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
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
PRIMARY
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
PRIMARY
ChEMBL
CHEMBL2111092
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
INN
8630
Created by admin on Fri Dec 15 16:11:16 GMT 2023 , Edited by admin on Fri Dec 15 16:11:16 GMT 2023
PRIMARY
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ACTIVE MOIETY