83480-29-9 Usage
Description
Voglibose, an orally active α-D-glucosidase inhibitor, is a potent and effective medication used for the treatment of postprandial hyperglycemia in diabetic patients. It works by decreasing the release of glucose from carbohydrate ingestion and slowing the increase of postprandial blood glucose levels. Voglibose is much more potent and has fewer side effects than other agents in its class, such as acarbose. It is a colorless crystalline solid and is available under the brand names Basen and Glustat.
Uses
Used in Pharmaceutical Industry:
Voglibose is used as an anti-diabetic drug for treating diabetes. It is specifically used for lowering post-prandial blood glucose levels, thereby reducing the risk of macrovascular complications in diabetic patients.
Used in Diabetes Management:
Voglibose is used as an α-glucosidase inhibitor for the treatment of diabetes. It helps in managing carbohydrate-dependent metabolic disorders such as obesity by maintaining low plasma levels of glucose, triglyceride, and insulin.
Used in Research:
Voglibose is used to study its benefits as a protectant against ischemia-reperfusion injury through glucagon-like peptide 1 receptors and the phosphoinositide 3-kinase-Akt-endothelial nitric oxide synthase pathway.
Oral hypoglycemic agents
Voglibose is an oral hypoglycemic agents which can alleviate the postprandial hyperglycemia of diabetes patients. It is first successfully developed by the Takeda Company in Japan. It belongs to α-glucosidase inhibitor (a drug which can delay the intestinal absorption of carbohydrates to achieve hypoglycemic effect). Its mechanism of action is through inhibiting the activity of disaccharides hydrolase (α-glucosidase) which can hydrolyze disaccharide into monosaccharide inside the gut and thus delaying the digestion and absorption of sugar and further alleviating the postprandial hyperglycemia. In the assay of measuring the exhaled hydrogen of healthy adults given sucrose loading, the results have confirmed that this drug in its clinical dosage has an inhibitory effect on hyperglycemia. When normal rats are subject to oral administration, this product can inhibit the increased blood sugar level after the increased loading of starch, sucrose, glucose and maltose, while it has no inhibitory effect on the increased blood sugar after increased loading of glucose, fructose, and lactose. In vitro analysis of mechanism of action have shown that, for the maltase and sucrose obtained from the small intestine of pig and rat, this drug has a strong inhibitory effect; on the other hand, it has a relative low inhibitory effect on the pancreatic α-amylase of pig and rat and has no inhibitory effect on β-glucosidase. It has a competitive inhibitory effect on the disaccharide hydrolase of the isomaltase-sucrase complex from the rat small intestine.
It is understood that voglibose has a broad scope of application; it is not only suitable for elderly patients with diabetes, but also has significant efficacy on patients with refractory type II diabetes, patients with secondary failure of sulfonylureas, patients with combined hyperlipidemia diabetes, patients with merged cardiovascular diabetes disease as well as patients with combined hyperinsulinemia. Because this product does not stimulate the secretion of insulin, it can reduce the harmful effects of postprandial hyperinsulinemia, reducing the resistance of insulin and contributes to the prevention and treatment of metabolic syndrome such as cardiovascular complications.
Side Effects
Mechanism of occurrence of side effects of oral administration of hypoglycemic agents is generally that: when the unabsorbed carbohydrate enters into the large intestine, under the action of bacteria, it subjects to glycolysis which produces carbon dioxide, hydrogen, and organic acids. At the same time, because of the increased osmotic pressure of intestinal, water retention happen which therefore causes increased exhausting, bloating, and diarrhea. Since voglibose can selectively inhibit the activity of the disaccharide hydrolase in the intestine, further delaying the rapid digestion and absorption of carbohydrate in the upper small intestine, and thus reducing saccharide, leading to a lower incidence of adverse reactions. It is known to have the following adverse reactions:
1. The digestive system: diarrhea, loose stools, borborygumus, abdominal pain, constipation, loss of appetite, nausea, vomiting, heartburn (incidence of 0.1 to 5%), stomatitis, thirst, abnormal taste, and pneumatosis cystoides gastrointestinalis (0.1%).
2. Allergic symptoms: rash, itching, light sensitivity (incidence of 0.1% or less).
3. Liver: GOT, GPT, LDH, γ-GTP, ALP are increased (0.1% incidence).
4. The nervous system: headache, dizziness, staggering, drowsiness (0.1% incidence).
5. The blood system: anemia (incidence of 0.1 to 5%), thrombocytopenia (0.1%).
6. Other: paralysis, facial swelling, hazy eyes, fever, flu, tiredness, feeling of fatigue, hyperkalemia, rise of serum amylase, decrease of high-density lipoprotein, sweating, hair loss (incidence of 0.1%).
The above information is edited by the lookchem of Dai Xiongfeng.
Originator
Takeda (Japan)
Manufacturing Process
N-(1,3-Dihydroxy-2-propyl)valiolamine:To a solution of 2.0 g of valiol amine in 50 ml of N,N-dimethylformamide are
added 3.4 g of dihydroxyacetone, 1.5 ml of 2 N hydrochloric acid and 2.6 g of
sodium cyanoborohydride, followed by stirring at 60 to 70°C for 16 hours. The
reaction solution is concentrated under reduced pressure to distill off the N,N-
dimethylformamide as much as possible, and the residue is dissolved in 100 ml of water. The solution is made acid with 2 N hydrochloric acid, stirred for
30 to 40 minutes under ice-cooling, adjusted to pH 4.5 with 1 N sodium
hydroxide solution and subjected to column chromatography (250 ml) on
Dowex 50W x 8 (H + type) (produced by Dow Chemical of the United States of
America). After the washing with water, the elution is carried out with 0.5 N
aqueous ammonia. The eluate is concentrated under reduced pressure, and
the concentrate is chromatographed on a column (250 ml) of Amberlite CG-50
(NH 4 + type) (produced by Rohm and Haas Co. of the United States of
America), followed by the elution with water. The eluate is concentrated under
reduced pressure, and the concentrate is lyophilized to give 2.0 g of white
powder of N-(1,3-dihydroxy-2-propyl)valiol amine.Ethanol (about 60 ml) is added to the above lyophilized product (1.2 g) of N-
(1,3-dihydroxy-2-propyl)valiol amine, and the mixture is warmed for 30
minutes in a hot water bath (the bath temperature: 90-95°C), followed by
leaving on standing in a refiegerator. The resultant crystalline substance is
recovered by filtration, washed with ethanol and then dried in a desiccator
under reduced pressure. Yield of 0.95 g. MP: 162-163°C. [α] D 25 = +26.2° (c
= 1, H 2 O).
Therapeutic Function
Antidiabetic, Antiobesity
World Health Organization (WHO)
Acarbose and voglibose area-glucosidase inhibitors and delay
digestion/absorption of carbohydrates as well as improving postprandial
hyperglycaemia.
Biological Activity
Orally active α -glucosidase inhibitor (IC 50 values are 3.9 and 6.4 nM at sucrase and maltase respectively). Increases glucagon-like peptide 1 (GLP-1) secretion and decreases food consumption in ob/ob mice, and reduces plasma concentrations of glucose, triglycerides and insulin in Wistar fatty rats. Exhibits antidiabetic and antiobesity activity in vivo .
Check Digit Verification of cas no
The CAS Registry Mumber 83480-29-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,4,8 and 0 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 83480-29:
(7*8)+(6*3)+(5*4)+(4*8)+(3*0)+(2*2)+(1*9)=139
139 % 10 = 9
So 83480-29-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7?,8+,9-,10?/m0/s1
83480-29-9Relevant articles and documents
Synthesis method of voglibose
-
, (2021/08/07)
The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.
Preparation method of voglibose
-
Paragraph 0007; 0019-0022, (2019/10/22)
The invention discloses a preparation method of voglibose. The preparation method comprises the steps of adopting tetrabenzyl voltolose as a raw material for a reaction in an aprotic solvent in the presence of boron halide, and adding a basic substance for crystallization, suction filtration and recrystallization to obtain the high-purity and high-yield voglibose after the reaction is completed. The whole synthesis process has the advantages that the raw material cost is extremely low, the reaction time is short, and the product yield and the quality are high; the method is suitable for industrial production.
Amino sugar compound and preparation method and application thereof
-
, (2017/09/13)
The invention discloses an amino sugar compound as shown in formula I, a preparation method of the amino sugar compound and application of the amino sugar compound to the preparation of a compound as shown in formula A.