Thiamine
Thiamine
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Thiamine

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Catalog Number PR70166
CAS 70-16-6
Structure
Description Thiamine(1+) is a primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a primary alcohol and a vitamin B1. It is a conjugate base of a thiamine(2+).
Synonyms vitamin B1
IUPAC Name 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
Molecular Weight 265.36
Molecular Formula C12H17N4OS+
InChI JZRWCGZRTZMZEH-UHFFFAOYSA-N
InChI Key InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
Associated Therapies Nutritional supplementation, Vitamin supplementation, Dietary supplementation
Drug Categories Alimentary Tract and Metabolism; Diet, Food, and Nutrition; Food; Growth Substances; Micronutrients; OCT1 substrates; OCT2 Inhibitors; Physiological Phenomena; Pyrimidines; Sulfur Compounds; Thiazoles; Vitamin B Complex; Vitamins
Drug Interactions Acyclovir-The risk or severity of adverse effects can be increased when Acyclovir is combined with Thiamine.
Amantadine-The serum concentration of Amantadine can be increased when it is combined with Thiamine.
Chlorpheniramine-The risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Thiamine.
Choline salicylate-The serum concentration of Choline salicylate can be increased when it is combined with Thiamine.
Cimetidine-The risk or severity of adverse effects can be increased when Cimetidine is combined with Thiamine.
Isomeric SMILES CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
Type Small Molecule
Therapeutic Category Supplyments
Pharmacology

Indications

Thiamine is primarily indicated for the treatment of conditions associated with thiamine and niacin deficiency. These include Korsakoff's alcoholic psychosis, Wernicke-Korsakoff syndrome, delirium, and peripheral neuritis. By addressing deficiencies in these critical nutrients, thiamine plays a vital role in managing and alleviating the symptoms of these disorders.

Pharmacodynamics

Thiamine serves multiple physiological roles due to its diverse pharmacodynamic properties. It acts as an antioxidant and has erythropoietic, cognition-, and mood-modulating effects. Moreover, thiamine exhibits antiatherosclerotic and detoxification activities. Research indicates that it can mitigate lead-induced lipid peroxidation in the liver and kidneys of rats. Thiamine deficiency is known to cause selective neuronal death, likely due to increased free radical production, suggesting oxidative stress as an early contributor to brain damage. Additionally, thiamine is essential in intracellular glucose metabolism, affecting arterial smooth muscle and endothelial cell proliferation, which is crucial in preventing atherosclerosis, particularly in hyperglycemic conditions.

Absorption

Thiamine is primarily absorbed in the duodenum, utilizing both active and passive transport mechanisms.

Metabolism

Hepatic.

Mechanism of Action

The mechanism of action of thiamine involves influencing endothelial cell function by potentially reducing intracellular protein glycation and directing glycolytic pathways. While thiamine itself serves as the primary transport form of the vitamin, its phosphorylated derivatives-thiamine monophosphate (ThMP), thiamine diphosphate (ThDP or thiamine pyrophosphate, TPP), thiamine triphosphate (ThTP), and adenosine thiamine triphosphate (AThTP)-constitute the active forms that act as coenzzymes and perform distinct biological functions.

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