U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H26N4O3S2.ClH
Molecular Weight 435.007
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FURSULTIAMINE HYDROCHLORIDE

SMILES

C/C(=C(/CCO)\SSCC1CCCO1)/N(Cc2cnc(C)[nH]c2=N)C=O.Cl

InChI

InChIKey=OPGOLNDOMSBSCW-CLNHMMGSSA-N
InChI=1S/C17H26N4O3S2.ClH/c1-12(16(5-6-22)26-25-10-15-4-3-7-24-15)21(11-23)9-14-8-19-13(2)20-17(14)18;/h8,11,15,22H,3-7,9-10H2,1-2H3,(H2,18,19,20);1H/b16-12+;

HIDE SMILES / InChI
Fursultiamine, also known as thiamine tetrahydrofurfuryl disulfide (TTFD) is an oral FDA- approved thiamine derivative for treating vitamin B1 deficiency and is very rapidly metabolized into thiamine. Fursultiamine possesses a mild beneficial effect in patients with Alzheimer's disease. The improvement could be observed not only in their emotional or other mental symptoms but also in intellectual function. Only mildly impaired subjects showed cognitive improvement. In addition was shown, that fursultiamine have a beneficial clinical effect on some autistic children. Some relatively recent experiments have revealed that fursultiamine was a unique antagonist of hepcidin in vitro that could serve as a template for the development of drug candidates that inhibit the hepcidin-ferroportin interaction. This inhibition is a key for the treatment of anemia of inflammation (AI), a common in patients with infection, autoimmune diseases, cancer, and chronic kidney disease.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study.
2002 Aug
Thiamine tetrahydrofurfuryl disulfide: a little known therapeutic agent.
2004 Sep
Fursultiamine, a vitamin B1 derivative, enhances chondroprotective effects of glucosamine hydrochloride and chondroitin sulfate in rabbit experimental osteoarthritis.
2005 Jun
Patents

Sample Use Guides

Single administration of 100 mg of thiamin tetrahydrofurfuryl disulfide
Route of Administration: Oral
To explore new therapeutic options for Anemia of inflammation (AI) and other iron-related disorders caused by hepcidin excess, there was developed a cell-based screen to identify hepcidin antagonists. Of the 70,000 small molecules in the library, it was identified 14 compounds that antagonized the hepcidin effect on ferroportin. One of these was fursultiamine. To fully characterize fursultiamine as a hepcidin antagonist, there was examined its dose-dependent effect on cellular iron export. Fpn-GFP cells were treated with 100 ng/ml hepcidin and 0–50 μM fursultiamine for 24 hours, and intracellular ferritin concentration was determined. Fursultiamine reversed the effect of hepcidin on ferritin levels, with the IC50 dose in the submicromolar range.
Name Type Language
FURSULTIAMINE HYDROCHLORIDE
JAN   JP   WHO-DD  
Common Name English
FURSULTIAMINE HYDROCHLORIDE [JAN]
Common Name English
FURSULTIAMINE HYDROCHLORIDE [WHO-DD]
Common Name English
ALINAXIN
Brand Name English
FURSULTIAMINE HYDROCHLORIDE [JP]
Common Name English
THIAMINE TETRAHYDROFURFURYL DISULFIDE HYDROCHLORIDE
Common Name English
N-((4-AMINO-2-METHYLPYRIMIDIN-5-YL)METHYL)-N-((1E)-4-HYDROXY-1-METHYL-2-((TETRAHYDROFURAN-2-YLMETHYL)DISULFANYL)BUT-1-EN-1-YL)FORMAMIDE HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
EVMPD
SUB21942
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL1740659
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
218-278-9
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
DRUG BANK
DBSALT002919
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
EPA CompTox
2105-43-3
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
CAS
2105-43-3
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
FDA UNII
T3557LWB27
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY
PUBCHEM
9845819
Created by admin on Sat Jun 26 06:28:55 UTC 2021 , Edited by admin on Sat Jun 26 06:28:55 UTC 2021
PRIMARY