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HomeProduct name listVoglibose

Voglibose

Synonym(s):3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol;N-(1,3-Dihydroxyprop-2-yl)valiolamine

  • CAS NO.:83480-29-9
  • Empirical Formula: C10H21NO7
  • Molecular Weight: 267.28
  • MDL number: MFCD00865496
  • EINECS: 1312995-182-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
Voglibose Structural

What is Voglibose?

Description

Voglibose was introduced in Japan for the treatment of postprandial hyperglycemia in diabetic patients. As an orally active α-D-glucosidase inhibitor, it is effective in decreasing the release of glucose from carbohydrate ingestion and slowing the increase of postprandial blood glucose levels, as demonstrated in animals and humans following sucrose and starch loading. In addlion, voglibose was reported to have prophylactic effect in genetically obese Wistar rats, maintaining low plasma levels of glucose, triglyceride and insulin, indicating a potential usefulness for the management of other carbohydrate-dependent metabolic disorders such as obesity. Voglibose is much more potent and has fewer side effects than acarbose, another agent in its class.

Chemical properties

Colourless Crystalline Solid

Originator

Takeda (Japan)

The Uses of Voglibose

Voglibose is an α-glucosidase inhibitor, similar to acarbose and miglitol, used for lowering post-prandial hyperglycemia (PPHG) in people with diabetes mellitus. Voglibose is used to study it 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.

The Uses of Voglibose

An alpha-Glucosidase inhibitor used as an antidiabetic

The Uses of Voglibose

An α-Glucosidase inhibitor used as an antidiabetic.

The Uses of Voglibose

For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.

What are the applications of Application

Voglibose is an α-glucosidase inhibitor that increases glucagon-like peptide 1 secretion

Definition

ChEBI: Voglibose is an organic molecular entity.

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).

brand name

Basen (Takeda); Glustat (Takeda).

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.

General Description

The most potent -glucosidase inhibitor is the valiolamine derivative voglibose. Compared with acarbose its inhibitory potency in vitro, depending on the -glucosidase enzyme, is up to 200 times higher. In Japan, daily dosages are only 0.3 – 0.9 mg, however, therapeutic efficacy on HbA1c reduction could not be clearly demonstrated with those dosages. HbA1c, a glycated hemoglobin species, which occurs in blood, is a diagnostic measure for the non-enzymatic glycation process, and depends on the plasma glucose concentration. The process of protein glycation is discussed to be responsible for the development of diabetic complications (neuropathy, retinopathy, nephropathy). In Europe voglibose is under evaluation with distinctly higher daily dosages of 1.5 to 6 mg. In contrast to acarbose, the smaller inhibitors of the monosaccharide type (miglitol, emiglitate, voglibose) do not inhibit pancreatic -amylase.

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 .

Properties of Voglibose

Melting point: 162-163°C
alpha  D25 +26.2° (c = 1 in water)
Boiling point: 601.9±55.0 °C(Predicted)
Density  1.58±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  DMSO (Slightly), Methanol (Very Slightly, Heated), Water (Sparingly, Sonicated)
form  Solid
pka 13.26±0.70(Predicted)
color  White to Off-White
Merck  14,10029
CAS DataBase Reference 83480-29-9(CAS DataBase Reference)

Safety information for Voglibose

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Voglibose

InChIKey FZNCGRZWXLXZSZ-CIQUZCHMSA-N

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