Sulbutiamine – (3286-46-2)

Sulbutiamine is a synthetic derivative of thiamine (vitamin B1) developed in Japan to treat asthenia or chronic fatigue. Its chemical structure consists of two modified thiamine molecules linked by a disulfide bridge, enhancing its lipophilicity and allowing it to cross the blood-brain barrier more effectively than regular thiamine. Once in the brain, Sulbutiamine is metabolized back into thiamine molecules, which participate in various biochemical processes.

Sulbutiamine primarily works by increasing thiamine and its phosphate esters in the brain, optimizing energy metabolism pathways such as the decarboxylation of pyruvate to acetyl-CoA and the citric acid cycle. This leads to increased ATP production, which is crucial for neurons with high energy demands. Additionally, Sulbutiamine modulates neurotransmitter systems by increasing the release of dopamine and glutamate, enhancing cognitive performance, improving mood, and providing neuroprotective effects.

The compound also upregulates high-affinity choline transporters, facilitating choline uptake into neurons and supporting the synthesis of acetylcholine, a neurotransmitter essential for memory and learning. Furthermore, Sulbutiamine exhibits antioxidant properties, protecting neuronal cells from oxidative damage and contributing to its neuroprotective effects.

The above information is displayed for information purpose only, and has not been reviewed by EON nor does EON attests or validates the accuracy nor does it constitutes a recommendation or validation.

Sulbutiamine is a synthetic derivative of thiamine (vitamin B1) developed in Japan to treat asthenia or chronic fatigue. Its chemical structure consists of two modified thiamine molecules linked by a disulfide bridge, enhancing its lipophilicity and allowing it to cross the blood-brain barrier more effectively than regular thiamine. Once in the brain, Sulbutiamine is metabolized back into thiamine molecules, which participate in various biochemical processes.

Sulbutiamine primarily works by increasing thiamine and its phosphate esters in the brain, optimizing energy metabolism pathways such as the decarboxylation of pyruvate to acetyl-CoA and the citric acid cycle. This leads to increased ATP production, which is crucial for neurons with high energy demands. Additionally, Sulbutiamine modulates neurotransmitter systems by increasing the release of dopamine and glutamate, enhancing cognitive performance, improving mood, and providing neuroprotective effects.

The compound also upregulates high-affinity choline transporters, facilitating choline uptake into neurons and supporting the synthesis of acetylcholine, a neurotransmitter essential for memory and learning. Furthermore, Sulbutiamine exhibits antioxidant properties, protecting neuronal cells from oxidative damage and contributing to its neuroprotective effects.

The above information is displayed for information purpose only, and has not been reviewed by EON nor does EON attests or validates the accuracy nor does it constitutes a recommendation or validation.
Sources:
https://en.wikipedia.org/wiki/Sulbutiamine
https://pubchem.ncbi.nlm.nih.gov/compound/20055424
https://www.medchemexpress.com/Sulbutiamine.html
https://www.medkoo.com/products/22742
https://pmc.ncbi.nlm.nih.gov/articles/PMC7210561/
https://synapse.patsnap.com/article/what-is-the-mechanism-of-sulbutiamine
Other Names

Bisibuthiamine

IUPAC Name

[(Z)-4-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-3-[[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulfanyl]pent-3-enyl] 2-methylpropanoate

CAS

3286-46-2

Molecular Weight

702.9

Molecular Formula

C32H46N8O6S2

SMILES

CC1=NC=C(C(=N1)N)CN(/C(=C(\SS/C(=C(\N(C=O)CC2=CN=C(N=C2N)C)/C)/CCOC(=O)C(C)C)/CCOC(=O)C(C)C)/C)C=O

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