Fursultiamine Chemical Properties

Melting point:

130-136°C (decompos.)

Boiling point:

652.3±55.0 °C(Predicted)

Density 

1.29

refractive index 

1.6270 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF).

form 

Solid

pka

14.42±0.10(Predicted)

color 

White to Off-White

CAS DataBase Reference

804-30-8(CAS DataBase Reference)

Safety Information

Toxicity

LD50 in rats (mg/kg): 2200 orally; 540 i.p. (Yurugi, Fushimi)

Fursultiamine Usage And Synthesis

Description

Fursultiamine (syn. thiamine tetrahydrofurfuryl disulfide) is a vitamin B1 derivative which is rarely used, is only sparingly soluble in water and thus is usually employed only for solid drug forms. Lyophilisates are stabilized by sodium dextran sulfate.

Chemical Properties

white or slightly yellow crystalline powder. melting point 130-136 °C (decomposition). soluble in methanol, ethanol, chloroform, slightly soluble in acetone, insoluble in benzene, ether, slightly garlic odor.

Originator

Alinamin F,Takeda,Japan,1961

Uses

Fursultiamine is an oral source of thiamine, used in comparative pharmacokinectic analysis of thiamine and it’s phosphorylated metabolites administered as multivitamin preparations, identification of drug candidate against prostate cancer from aspect of somatic cell reprogramming, therapeutic tool in number of human neurological diseases.

Application

Fursultiamine, a lipophilic vitamin B1 derivative, which is more readily absorbed in large amounts in the small intestine and has a longer half-life than its active counterpart vitamin B1. It is suitable for the treatment of beriberi or Wernicke encephalopathy due to vitamin B1 deficiency. It can also be used for the adjuvant treatment of peripheral neuritis and indigestion caused by vitamin B1 deficiency.

Preparation

Furanthiamine is obtained by condensing thiamine hydrochloride with sodium tetrahydrofuranmethyl thiosulfate after ring opening.

Definition

ChEBI: Fursultiamine is a member of pyrimidines.

Manufacturing Process

To a solution of 20 parts of thiamine hydrochloride in 30 parts of water is added an aqueous solution of sodium hydroxide (7.2 parts of NaOH in 30 parts of water), and the mixture is cooled with water. The mixture is allowed to stand for 30 minutes, 60 parts of chloroform is added, followed by a solution of 30 parts of crude sodium tetrahydrofurfurylthiosulfate in 30 parts of water, and the whole is stirred for 30 minutes. The chloroform layer is separated and the aqueous layer is extracted twice with 20 parts of chloroform. All the chloroform solutions are combined and shaken with 50 parts of 5% hydrochloric acid. The acid solution is decolorized and neutralized with alkali carbonate, whereupon thiamine tetrahydrofurfuryl disulfide separates out in the resinous state but soon solidifies [MP 129°C (decamp.)] . The yield is 16 parts. Recrystallization from ethyl acetate gives colorless prisms melting at 132°C (decomp.).

Therapeutic Function

Enzyme cofactor vitamin

Fursultiamine(804-30-8)Related Product Information

• Methylene dithiocyanate
• Methylparaben
• Acetonitrile
• Paraquat dichloride
• DL-Dithiothreitol
• Methanol
• Methyl acrylate
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• Dimethyl disulfide
• Furan
• CHLOROPHOSPHONAZO III
• Kresoxim-methyl
• Selenium sulfide
• Basic Violet 1
• Methyl
• Fursultiamine HCL JP
• Thiamine chloride
• Thiamine disulfide