Benfotiamine
[CAS# 22457-89-2]

Identification

• Classification: API >> Drugs that affect tissue metabolism
• Name: Benfotiamine
• Synonyms: N-((4-Amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydroxy-2-mercapto-1-methyl-1-butenyl)formamide-S-benzoate dihydrogen phosphate
• Molecular Formula: C₁₉H₂₃N₄O₆PS
• Molecular Weight: 466.45
• CAS Registry Number: 22457-89-2
• EC Number: 245-013-4
• SMILES: CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(CCOP(=O)(O)O)/SC(=O)C2=CC=CC=C2)/C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Discovery and Applications

Benfotiamine is a synthetic derivative of thiamine (vitamin B1) with the chemical formula C₁₁H₁₆N₄OS₂. It was developed to improve the bioavailability and efficacy of thiamine, thereby providing better therapeutic effects.

Benfotiamine was first synthesized in the 1950s by Japanese researchers who were looking for ways to improve the stability and absorption of thiamine. Unlike thiamine, which is water-soluble and prone to rapid degradation, benfotiamine is a fat-soluble compound. This property significantly improves its absorption and utilization in the body. This discovery was designed to overcome the limitations of traditional thiamine supplements and enhance their therapeutic effects.

The synthesis of benfotiamine involves the chemical modification of thiamine. The process first reacts thiamine to form a stable thiazole ring structure. A benzoyl group is then introduced to produce benfotiamine, enhancing its lipophilicity and stability. The product is finally purified to obtain benfotiamine in pure form, suitable for supplements and drugs.

Benfotiamine is widely used in the treatment of diabetes and its complications. Research shows that it can improve glucose metabolism and reduce oxidative stress. Clinical studies have shown that benfotiamine can help relieve diabetic neuropathy, a common diabetes complication characterized by nerve damage. By increasing thiamine levels, it helps protect nerve cells from damage and supports better nerve function.

Benfotiamine has benefits for nerve health, especially in cases involving oxidative stress and neurodegeneration. It is studied for its potential to treat neurodegenerative diseases such as Alzheimer's disease and other forms of dementia. It is able to cross the blood-brain barrier and act as an antioxidant, helping to protect brain health.

The compound has also been studied for its cardiovascular benefits. Studies have shown that benfotiamine has a positive impact on vascular health by reducing inflammation and oxidative stress. It helps control high blood pressure and supports overall cardiovascular function.

Benfotiamine is used to relieve pain associated with a variety of conditions, including neuropathic pain. Its effects in reducing oxidative damage and improving nerve health make it effective in managing chronic pain and improving the quality of life for pain patients.

In the supplement industry, benfotiamine is marketed as a dietary supplement for general health. Its higher bioavailability compared to standard thiamine makes it a popular choice for those seeking additional metabolic and neurological health support.

References

2024. Protocol for a seamless phase 2A-phase 2B randomized double-blind placebo-controlled trial to evaluate the safety and efficacy of benfotiamine in patients with early Alzheimer’s disease (BenfoTeam). *PLOS ONE*, 19(5).
DOI: 10.1371/journal.pone.0302998

2023. Synthetic Thioesters of Thiamine: Promising Tools for Slowing Progression of Neurodegenerative Diseases. *International Journal of Molecular Sciences*, 24(14).
DOI: 10.3390/ijms241411296

2022. Benfotiamine protects against hypothalamic dysfunction in a STZ-induced model of neurodegeneration in rats. *Life Sciences*, 307.
DOI: 10.1016/j.lfs.2022.120841