Welcome to LookChem.com Sign In|Join Free

CAS

  • or

83480-29-9

Post Buying Request

83480-29-9 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

83480-29-9 Usage

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.

Uses

Different sources of media describe the Uses of 83480-29-9 differently. You can refer to the following data:
1. 1. It is used for treating diabetes. 2. Anti-diabetic drug.
2. An α-Glucosidase inhibitor used as an antidiabetic.
3. For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.
4. An alpha-Glucosidase inhibitor used as an antidiabetic
5. 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.

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)

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.

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

83480-29-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (V0119)  Voglibose  >98.0%(HPLC)(T)

  • 83480-29-9

  • 100mg

  • 1,200.00CNY

  • Detail

83480-29-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Voglibose

1.2 Other means of identification

Product number -
Other names Glustat

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:83480-29-9 SDS

83480-29-9Synthetic route

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol
115250-39-0

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; palladium In methanol Ambient temperature;94%
With boron trifluoride diethyl etherate; diisopropylamine In tetrahydrofuran at 15 - 30℃; Reagent/catalyst; Solvent;82.86%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In tetrahydrofuran; methanol; water at 20℃; under 2206.72 - 2574.5 Torr; for 3h;
dihydroxyacetone
96-26-4

dihydroxyacetone

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane
83465-22-9

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 24h;85%
With hydrogenchloride; water; sodium cyanoborohydride In water; N,N-dimethyl-formamide at 70℃; for 16h;82%
With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 50 - 60℃; for 15h;73%
Stage #1: dihydroxyacetone; (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: With sodium cyanoborohydride In water; N,N-dimethyl-formamide at 20℃; for 16h;
3 g
C42H41NO13

C42H41NO13

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
In water for 24h; Reflux;85%
C10H19NO7

C10H19NO7

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; N,N-dimethyl-formamide at 0 - 50℃; for 24h; Reagent/catalyst; Temperature;80%
3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-1,5,6-tris-O-(phenylmethyl)-D-epi-inositol

3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-1,5,6-tris-O-(phenylmethyl)-D-epi-inositol

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; water; palladium In methanol at 20 - 60℃; for 6h;65%
(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol
115250-38-9

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / NaBH3CN / methanol / 16 h / Ambient temperature
2: 94 percent / 90 percent formic acid, Pd-black / methanol / Ambient temperature
View Scheme
voglibose hydrochloride
849419-34-7

voglibose hydrochloride

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With triethylamine In methanol for 1h; pH=~ 8.8 - ~ 9.0;
(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol
115250-39-0

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

A

4-benzyl-voglibose

4-benzyl-voglibose

B

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
With formic acid; palladium on activated charcoal In methanol; water Inert atmosphere;A 0.7 g
B 16 g
valienamine
38231-86-6

valienamine

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 5 h / 0 - 20 °C
1.2: 48 h / 40 °C
1.3: 6 h / 0 - 20 °C
2.1: sodium tetrahydroborate / N,N-dimethyl-formamide; methanol / 24 h / 0 - 50 °C
3.1: hydrogenchloride; sodium cyanoborohydride / N,N-dimethyl-formamide / 24 h / 60 °C
View Scheme
N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine
82920-27-2

N-<2-hydroxy-1-(hydroxymethyl)ethyl>valienamine

voglibose
83480-29-9

voglibose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; acetonitrile / 3 h / 0 - 20 °C
1.2: 24 h / 40 °C
1.3: 3.5 h / 0 - 20 °C
2.1: sodium tetrahydroborate / N,N-dimethyl-formamide; methanol / 24 h / 0 - 50 °C
View Scheme
C24H40N2O5

C24H40N2O5

voglibose
83480-29-9

voglibose

C30H56N2O9

C30H56N2O9

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 25℃; for 0.5h;
voglibose
83480-29-9

voglibose

(R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one(tartrate)

(R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one(tartrate)

83480-29-9Relevant articles and documents

Synthesis method of voglibose

-

Paragraph 0060; 0061; 0096-0098, (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.

Method for preparing voglibose and corresponding intermediate

-

Paragraph 0152-0154, (2019/01/23)

The invention relates to a novel intermediate for preparing voglibose and a preparation method of the voglibose. In particular, the intermediate is shown as a formula II as shown in the specification.The intermediate is prepared by a reaction of a compound shown as a formula I with peroxide; in addition, the intermediate can be hydrolyzed to form valiolamine; and voglibose is further synthesized.The method is simple, environmentally-friendly and high in yield.

Amino sugar compound and preparation method and application thereof

-

Paragraph 0060; 0068; 0069, (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.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 83480-29-9