Description
Buformin is a biguanide derivative with antihyperglycemic activity. It delays absorption of glucose from the gastrointestinal tract, increases insulin sensitivity and glucose utilization in peripheral cells, and inhibits hepatic gluconeogenesis. It can also deactivate the glycolytic pathway by suppressing glyceraldehyde 3-phosphate dehydrogenase gene expression, which can lead to lactic acidosis. Biguanides, such as buformin, are reported to inhibit the mitochondrial respiratory complex I by inhibiting ubiquinone reduction and by stimulating reactive oxygen species production
via the complex I flavin. Some biguanides, including buformin, can also inhibit the mitochondrial ATP synthase. Buformin has also been examined for antitumor activity due to its ability to disrupt the unfolded protein response transcription program during glucose deprivation, which induces cell death in glucose-deprived tumor cells.
Chemical Properties
White Solid
Originator
Silubin,Protochemie,Switz.
Uses
Buformin, clinically used for diabetes mellitus, is known to improve resistance to insulin in patients. It suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase.
Uses
BuforMin Hydrochloride is a biguanide derivative with antihyperglycemic activity. It delays absorption of glucose from the gastrointestinal tract, increases insulin sensitivity and glucose utilization in peripheral cells, and inhibits hepatic gluconeogenesis. BuforMin Hydrochloride has also been examined for antitumor activity due to its ability to disrupt the unfolded protein response transcription program during glucose deprivation, which induces cell death in glucose-deprived tumor cells.
Manufacturing Process
105.6 g of n-butylamine hydrochloride and 79.3 g of dicyandiamide were
ground intimately and mixed. The mixture was heated by means of an oil
bath, gradually with stirring, and after thirty minutes when the internal
temperature had reached 150°C, an exothermic reaction ensued with internal
pressure rising to 178°C. The reaction mixture was removed from the oil bath
until the internal temperature had fallen to 150°C and then heating was
resumed at 150°C for one hour. The cooled fusion mixture was dissolved in 3
liters of acetonitrile and on cooling n-butyl-biguanide hydrochloride precipitated.
Therapeutic Function
Antidiabetic
References
[1] RUSSELL A. MILLER. Biguanides suppress hepatic glucagon signalling by decreasing production of cyclic AMP[J]. Nature, 2013, 494 7436: 256-260. DOI:
10.1038/nature11808[2] AKIKO YANO. Buformin suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase.[J]. Biological & pharmaceutical bulletin, 2006, 29 5: 1006-1009. DOI:
10.1248/bpb.29.1006[3] HANNAH R BRIDGES. Effects of metformin and other biguanides on oxidative phosphorylation in mitochondria.[J]. Biochemical Journal, 2014, 462 3: 475-487. DOI:
10.1042/bj20140620[4] SAKAE SAITO. Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation.[J]. Cancer research, 2009: 4225-4234. DOI:
10.1158/0008-5472.can-08-2689
