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.
Definition
ChEBI: Fursultiamine is a member of pyrimidines.
Preparation
Furanthiamine is obtained by condensing thiamine hydrochloride with sodium tetrahydrofuranmethyl thiosulfate after ring opening.
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
