Voglibose

ChemicalBook > CAS DataBase List > Voglibose

Oral hypoglycemic agents Side Effects Uses

Product Name: Voglibose
CAS No.: 83480-29-9
Chemical Name: Voglibose
Synonyms: 5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol;Basen;Jumeal;AO 128;A 71100;Glustat;Beigrace;Voglistat;VOGLIBOSE;Voglibose D5
CBNumber: CB4481287
Molecular Formula: C10H21NO7
Formula Weight: 267.28
MOL File: 83480-29-9.mol

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Voglibose Property

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
InChIKey: FZNCGRZWXLXZSZ-CIQUZCHMSA-N
CAS DataBase Reference: 83480-29-9(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 20/21/22-36/37/38
Safety Statements: 36/37-37/39-26
WGK Germany: 3
RTECS: NM7524600
HS Code: 2940.00.6000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 50359
Product name: Voglibose
Purity: ≥97.0% (TLC)
Packaging: 10mg
Price: $305
Updated: 2024/03/01

TCI Chemical

Product number: V0119
Product name: Voglibose
Purity: >98.0%(HPLC)(T)
Packaging: 100mg
Price: $170
Updated: 2024/03/01

Cayman Chemical

Product number: 14179
Product name: Voglibose
Purity: ≥95%
Packaging: 10mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 14179
Product name: Voglibose
Purity: ≥95%
Packaging: 50mg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 14179
Product name: Voglibose
Purity: ≥95%
Packaging: 100mg
Price: $139
Updated: 2024/03/01

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Voglibose Chemical Properties,Usage,Production

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 chemicalbook of Dai Xiongfeng.

Uses

1. It is used for treating diabetes.
2. Anti-diabetic drug.

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)

Uses

An α-Glucosidase inhibitor used as an antidiabetic.

Uses

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

Uses

An alpha-Glucosidase inhibitor used as an antidiabetic

Uses

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.

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 .

Voglibose Preparation Products And Raw materials

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View Lastest Price from Voglibose manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Voglibose 83480-29-9
Price: US $0.00/g
Min. Order: 1g
Purity: 99%min
Supply Ability: 1000 G
Release date: 2021-06-19

Baoji Guokang Bio-Technology Co., Ltd.

Product: Voglibose
Price: US $1050.00/g
Min. Order: 100g
Purity: 98%
Supply Ability: 1-100lkg
Release date: 2021-06-08

Hebei Weibang Biotechnology Co., Ltd

Product: Voglibose 83480-29-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-11-01

83480-29-9, VogliboseRelated Search:

Cyclohexanone Acetaminophen Tris(hydroxymethyl)aminomethane Molasses Trimethylolpropane Cyclohexane Glibornuride TETRABENZYL-VOGLIBOSE (R)-Valiolamine Voglibose D-epi-Inositol, 1-O-(cyclohexylmethyl)-3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)- (9CI) Acarbose Miglitol Pioglitazone hydrochloride D-epi-Inositol, 2-C-[(cyclohexylmethoxy)methyl]-3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]- (9CI) Valiolamine (S)-Valiolamine Voglibose Cyclohexanone Impurity 3 D-epi-Inositol, 6-O-(cyclohexylmethyl)-3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)- (9CI)

Voglistat

epi-Inositol, 2,3-dideoxy-2-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-4-C-(hydroxymethyl)-

2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol

Beigrace

Jumeal

Voglibose ,98%

3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol

N-(1,3-Dihydroxyprop-2-yl)valiolamine

(1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)aMino]-1-(hydroxyMethyl)cyclohexane-1,2,3,4-tetrol

D-epi-Inositol, 3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)

Voglibose 5-(1,3-Dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

VOGLIBOSE

3,4-DIDEOXY-4-[[2-HYDROXY-1-(HYDROXYMETHYL)ETHYL]AMINO]-2-C-(HYDROXYMETHYL)-D-EPIINOSITOL

3,4-DIDEOXY-4-[[2-HYDROXY-1-(HYDROXYMETHYL)ETHYL]AMINO]-2-C-(HYDROXYMETHYL)-D-EPINOSITOL

Voglibose Solution, 100ppm

5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

VOGLIBOSE, 99+%

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

A 71100

AO 128

Basen

D-epi-Inositol, 3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)- (9CI)

Glustat

N-(1,3-Dihydroxy-2-propyl)valiolamine

Voglibose Voglibose

(1S,2S,3R,4S,5S)-5-((1,3-Dihydroxypropan-2-yl)amino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol

Voglibose USP/EP/BP

5-(1,3-Dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-Tetro

Voglibose D5

VogliboseQ: What is Voglibose Q: What is the CAS Number of Voglibose Q: What is the storage condition of Voglibose Q: What are the applications of Voglibose

Voglibose CP GRADE

Voglibose extrapure, 98%

AO 128|||Glustat|||Basen

Voglibose Impurity 34

83480-29-9

480-29-9

3480-29-9

C10H21NO6

C10H21NO7

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