FURSULTIAMINE

First approved in 2018

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H26N4O3S2
Molecular Weight	398.543
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC2CCCO2

InChI

InChIKey=JTLXCMOFVBXEKD-FOWTUZBSSA-N

InChI=1S/C17H26N4O3S2/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)/b16-12+

HIDE SMILES / InChI

Molecular Formula	C17H26N4O3S2
Molecular Weight	398.543
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8815393 | https://www.ncbi.nlm.nih.gov/pubmed/15328496 | https://www.ncbi.nlm.nih.gov/pubmed/23292796

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.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Thiamine deficiency 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15328496	Primary	Approved 8583	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8815393	Palliative	Phase II 1147	Unknown Approved Use Unknown
Autism spectrum disorder 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12195231	Palliative	Not Provided 511	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
349.8 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=16	10 mg single, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
340.6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=17	10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
237.7 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
439.8 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4142.9 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=16	10 mg single, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4004.4 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=17	10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1050.3 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1907.1 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.8 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=16	10 mg single, subcutaneous dose: 10 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.1 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/480235_3122401A2053_1_081_1F.pdf#page=17	10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		THIAMINE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27707509/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: RIBOFLAVIN TETRABUTYRATE	RIBOFLAVIN TETRABUTYRATE	THIAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8815393/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8815393/	Sources: https://pubmed.ncbi.nlm.nih.gov/8815393/
300 mg single, intravenous Highest studied dose Dose: 300 mg Route: intravenous Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31534090/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31534090/	Sources: https://pubmed.ncbi.nlm.nih.gov/31534090/
500 mg 1 times / day multiple, oral Highest studied dose Dose: 500 mg, 1 times / day Route: oral Route: multiple Dose: 500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/413089/	unhealthy, NEWBORN Health Status: unhealthy Age Group: NEWBORN Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/413089/	Sources: https://pubmed.ncbi.nlm.nih.gov/413089/

PubMed

Title	Date	PubMed
Fursultiamine, a vitamin B1 derivative, enhances chondroprotective effects of glucosamine hydrochloride and chondroitin sulfate in rabbit experimental osteoarthritis.	2005-06	15973508
Thiamine tetrahydrofurfuryl disulfide: a little known therapeutic agent.	2004-09	15328496
Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study.	2002-08	12195231

Patents

Sample Use Guides

In Vivo Use Guide

Single administration of 100 mg of thiamin tetrahydrofurfuryl disulfide

Route of Administration: Oral

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:41:20 GMT 2025` Edited by `admin` on `Mon Mar 31 18:41:20 GMT 2025`
Record UNII	05J61265PX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALIARON F

Preferred Name

English

FURSULTIAMINE

Official 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

Systematic Name

English

ALINAMIN-F

Common Name

English

N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-N-(4-HYDROXY-1-METHYL-2-((TETRAHYDROFURFURYL)DITHIO)-1-BUTENYL)FORMAMIDE

Systematic Name

English

fursultiamine [INN]

Common Name

English

FURSULTIAMINE [MART.]

Common Name

English

TTFD

Code

English

FURSULTIAMIN

Common Name

English

FURSULTIAMINE [MI]

Common Name

English

Fursultiamine [WHO-DD]

Common Name

English

FURSULTIAMINE [JAN]

Common Name

English

Classification Tree Code System Code

DSLD

3907 (Number of products:11)