Hubei Honest Biochemical Co., Ltd.

Glibenclamide CAS 10238-21-8

Product Name: Glibenclamide

Synonyms: LABOTEST-BB LT00244861;GLYBENCLAMIDE;GLYBENZCYCLAMIDE;GLYBURIDE;GIBENCLAMIDE;GLIBENCLAMIDE;5-CHLORO-N-[4-(CYCLOHEXYLUREIDOSULFONYL)PHENETHYL]-2-METHOXYBENZAMIDE;5-CHLORO-N-[2-[4-[[[(CYCLOHEXYLAMINO)CARBONYL]AMINO]-SULFONYL]PHENYL]ETHYL]-2-METHOXYBENZAMIDE

CAS: 10238-21-8

MF: C23H28ClN3O5S

MW: 494

EINECS: 233-570-6

Melting point 173-175°C

storage temp. 2-8°C

solubility ethanol: soluble2mg/mL

pka 5.3(at 25℃)

Water Solubility Soluble in ethanol (5 mg/mL), DMSO (25 mg/mL), chloroform (1:36), methanol (1:250), and DMF. Insoluble in water.

Hypoglycemic agents Glibenclamide belongs to the second generation oral sulfonylurea drugs with the mechanism of action being similar as tolbutamide and the hypoglycemic effect being strongest among sulfonylurea drugs. Its intensity of action is about 200 to 250 times of that of Tolbutamide. It can selectively act on the pancreatic β-cells, promote insulin secretion; can enhance the hypoglycemic effect of exogenous insulin and strengthen the post-receptor effect of insulin. It has fast oral absorption with high protein binding rate. It begins to take effect after 30 minutes with the effect being strongest at 1.5 hours and the duration of 16 to 24 hours. It has a distribution volume of 0.1L/kg, plasma protein binding rate of 90% to 95% and half-life of 4 to 8 hours. It is mainly consumed by the liver metabolism with six metabolites. Two of them are known as hydroxylated compounds with no hypoglycemic effect and is mainly excreted from the urine and a small amount is excreted by the stool. It is clinically mainly used for the treatment of mild to moderate non-insulin dependent diabetes mellitus.

Recently, an international study found that the commonly used diabetes drug glibenclamide can help the body's immune system to fight against certain bacterial infections, e.g. in the treatment of melioidosis, the mortality rate can be reduced by about half.

Melioidosis is a disease prevalent in tropical areas such as Southeast Asia and northern Australia. It is caused by Burkholderia pseudomallei with the symptoms including sepsis and pneumonia. The mortality rate is high. Diabetic patients tend to be more susceptible to melioidosis, but the mortality rate is lower compared with other patients.

Hypoglycemic effect Glibenclamide is currently one of the most commonly used drugs for the treatment of type 2 diabetes. Because this product has fast and strong effect, so the effect after the application remarkable, being able to have good control of blood sugar; being applicable for patients of high blood sugar who get bad efficacy when treated with other sulfonyl Urea hypoglycemic agents.

Two commonly sulfonylurea oral hypoglycemic agents are glibenclamide and glimepiride, the comparison of hypoglycemic effect of them two are as follow:

(1) The effect on glucose transport and metabolism: Glibenclamide and glimepiride can stimulate the key enzymes in the glucose metabolism and improve the glucose transporter (GLUT4) translocation/dephosphorylation to promote the glucose uptake of the surrounding tissue, specifically exhibited in glycogen synthesis and increased fat formation. Glycogen synthase and 3-phosphoglycerol fatty acyltransferase are the key enzymes in glycogen and fat synthesis, and glimepiride is more active than glibenclamide in activating these key enzymes, such as for activating glycogen synthase activity, glimepiride is 2.5 times that of glibenclamide; for the capability to activate lipase, glimepiride is 1.9 times that of glibenclamide. Glimepiride increased the expression of GLUT4 on the cell membrane by inducing dephosphorylation of GLUT4.

 (2) Effect on glycosylated-phosphatidylinositol-specific phospholipase (GPI-PLC): GPI is located in the outer layer of the cell membrane and participates in insulin signal transduction, which can interfere with glucose metabolism of muscle and adipocytes. GPI-PLC can shed the GPI, thereby improving the cell phosphorylation status. Insulin and sulfonylureas can activate GPI-PLC, helping muscle, adipose tissue for the uptake and transport of glucose. However, in the presence of insulin resistance, insulin itself is very difficult to activate GPI-PLC, but glimepiride can still activate the enzyme. In vitro and in vivo studies have shown that, glimepiride has the strongest pancreatic effect in sulfonylurea drugs, which can increase glucose synthesis by 2.5 times and fat synthesis by 4 times. The ratio of glimepiride to glibenclamide was 2: 1. Therefore, glimepiride has a lower secondary failure incidence than other sulfonylurea drugs.