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Fursultiamine
[CAS# 804-30-8]

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Identification
Classification API >> Vitamins and minerals >> Vitamin B drugs
Name Fursultiamine
Synonyms N-(4-Amino-2-methylpyrimidin-5-ylmethyl)-N-[4-hydroxy-1-methyl- 2-(tetrahydrofurfuryldithio)but-1-enyl]formamide
Molecular Structure CAS # 804-30-8, Fursultiamine, N-(4-Amino-2-methylpyrimidin-5-ylmethyl)-N-[4-hydroxy-1-methyl- 2-(tetrahydrofurfuryldithio)but-1-enyl]formamide
Molecular Formula C17H26N4O3S2
Molecular Weight 398.55
CAS Registry Number 804-30-8
EC Number 212-357-1
SMILES CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(\CCO)/SSCC2CCCO2)/C
Properties
Density 1.3±0.1 g/cm3 Calc.*
Melting point 130-136 ººC (decompos) (Expl.)
Boiling point 652.3±55.0 ºC 760 mmHg (Calc.)*
Flash point 348.3±31.5 ºC (Calc.)*
Index of refraction 1.626 (Calc.)*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H315-H320-H335    Details
Precautionary Statements P261-P280-P301+P312-P302+P352-P305+P351+P338    Details
SDS Available
up Discovory and Applicatios
Fursultiamine is a synthetic derivative of thiamine (vitamin B1) designed to enhance the bioavailability and lipid solubility of the parent vitamin. It was first developed in Japan in the 1960s as part of a series of chemical modifications aimed at improving thiamine absorption and therapeutic efficacy. The compound contains a disulfide-linked furan ring, which facilitates its passage through lipid membranes, allowing more efficient uptake in the gastrointestinal tract compared to water-soluble thiamine salts. This modification was particularly important in addressing deficiencies in populations with malabsorption disorders or increased metabolic demands.

Fursultiamine is used primarily in clinical nutrition to prevent or treat thiamine deficiency, which can lead to conditions such as beriberi, Wernicke’s encephalopathy, and peripheral neuropathy. Its enhanced lipophilicity allows for better penetration into cells, particularly in the nervous system, where thiamine plays a critical role as a cofactor for enzymes involved in carbohydrate metabolism and energy production. By increasing intracellular thiamine levels, fursultiamine helps restore normal enzymatic activity in pathways such as the pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase complexes, which are essential for ATP generation and neuronal function.

Beyond its use in thiamine deficiency, fursultiamine has been explored for its potential in managing metabolic and neurological disorders. Studies have indicated benefits in reducing fatigue, improving cognitive function, and supporting recovery in conditions associated with high oxidative stress or impaired energy metabolism. Its ability to cross cell membranes more readily than thiamine hydrochloride or thiamine pyrophosphate allows fursultiamine to achieve higher tissue concentrations, which is advantageous in both therapeutic and preventive contexts.

The compound is typically administered orally in the form of capsules or tablets, and it has demonstrated a favorable safety profile with minimal adverse effects when used at recommended doses. Its pharmacokinetic advantages make it a preferred choice in clinical scenarios requiring rapid correction of thiamine deficiency or enhanced cellular delivery. Fursultiamine is also of interest in sports nutrition and dietary supplementation, where improved energy metabolism and reduction of exercise-induced fatigue are desired outcomes.

Research has further investigated fursultiamine’s potential neuroprotective properties. By enhancing thiamine-dependent enzymatic activity, it may help mitigate neuronal damage in oxidative stress-related conditions, including diabetic neuropathy and ischemic injury. Additionally, its role in modulating energy metabolism has implications for supporting mitochondrial function and overall cellular health.

Overall, fursultiamine represents a significant advancement in vitamin B1 therapy, combining chemical modification with enhanced bioavailability to improve clinical outcomes. Its discovery and application reflect the broader effort to develop lipid-soluble derivatives of water-soluble vitamins to address deficiencies more effectively and support metabolic health. The compound continues to be utilized in clinical practice, nutritional supplementation, and research aimed at understanding its benefits in energy metabolism, nervous system function, and cellular protection.

References

2020. Fursultiamine Alleviates Choroidal Neovascularization by Suppressing Inflammation and Metabolic Reprogramming. Investigative Ophthalmology & Visual Science.
DOI: 10.1167/iovs.61.12.24

2021. PET imaging of 11C-labeled thiamine tetrahydrofurfuryl disulfide, vitamin B1 derivative: First-in-human study. Biochemical and Biophysical Research Communications.
DOI: 10.1016/j.bbrc.2021.03.119

2015. Synthesis of 11C-Labeled Thiamine and Fursultiamine for in Vivo Molecular Imaging of Vitamin B1 and Its Prodrug Using Positron Emission Tomography. The Journal of Organic Chemistry.
DOI: 10.1021/acs.joc.5b00685
Market Analysis Reports
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