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Voglibose

Voglibose structure

CAS No:
83480-29-9
Formula:
C10H21NO7
Chemical Name:
Voglibose
Synonyms:
D-epi-Inositol,3,4-dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-;3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epi-inositol;N-(1,3-Dihydroxy-2-propyl)valiolamine;Voglibose;AO 128;Glustat;A 71100;Basen;Voglistat;(1S,2S,3R,4S,5S)-5-[(1,3-Dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol;(1S,2S,3R,4S,5S)-5-((1,3-Dihydroxypropan-2-yl)amino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol;112653-29-9
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

Voglibose is an N-substituted derivative of valiolamine, excellent inhibitory activity against α-glucosidases and its action against hyperglycemia and various disorders caused by hyperglycemia.Target: α-glucosidasesglibose can inhibit the intestinal α-glucosidases, which are responsible for the digestion of disaccharides such as maltose and sucrose, including maltase and sucrase. The Ki values of Voglibose for sucrase and maltase are about 106and 105 times smaller than the Km values for

Solid

Voglibose is an organic molecular entity.|Voglibose is an alpha-glucosidase inhibitor used for lowering post-prandial blood glucose levels in people with diabetes mellitus. It is made in India by Ranbaxy Labs and sold under the trade name Volix.|Voglibose is a valiolamine derivative and inhibitor of alpha-glucosidase with antihyperglycemic activity. Voglibose binds to and inhibits alpha-glucosidase, an enteric enzyme found in the brush border of the small intestines that hydrolyzes oligosaccharides and disaccharides into glucose and other monosaccharides. This prevents the breakdown of larger carbohydrates into glucose and decreases the rise in postprandial blood glucose levels.

Voglibose Basic Attributes

Molecular Weight：

267.28

Exact Mass：

267.28

EC Number：

1312995-182-4

UNII：

S77P977AG8

DSSTox ID：

DTXSID2021442

NCI Thesaurus Code：

C95221

ATC Code：

A - Alimentary tract and metabolism

Characteristics

PSA：

154

XLogP3：

-4.1

Appearance：

Solid

Density：

1.6±0.1 g/cm3

Melting Point：

162-163°C

Boiling Point：

601.9°C at 760 mmHg

Flash Point：

274.1±22.1 °C

Refractive Index：

1.636

Water Solubility：

1.90e+02 g/L

Storage Conditions：

Store at -20°C

Specific rotation：

D25 +26.2° (c = 1 in water)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

20/21/22-36/37/38

safety instructions：

36/37-37/39-26

RTECS Number：

NM7524600

Marks：

Drug Information

Drug Indication：

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

Pharmacology：

Voglibose, an alpha-glucosidase inhibitor, is a synthetic compound with potent and enduring therapeutic efficacies against disorders of sensory, motor and autonomic nerve systems due to diabetes mellitus. The drug was approved in Japan in 1994 for the treatment of diabetes, and it is under further investigation by Takeda for the treatment of impaired glucose tolerance. Alpha-glucosidase inhibitors are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of complex carbohydrates (such as starch). Complex carbohydrates are normally converted into simple sugars (monosaccharides) which can be absorbed through the intestine. Hence, alpha-glucosidase inhibitors reduce the impact of complex carbohydrates on blood sugar.

MeSH：

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)|Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. (See all compounds classified as Glycoside Hydrolase Inhibitors.)

Absorption：

Slowly and poorly absorbed. The reported pharmacokinetic parameters of voglibose with metformin are Cmax corresponds to 1.38 mcg/ml while AUC is 8.17 mcg.h/ml and tmax is of 2.5 hours.

Metabolism/Metabolites：

Little metabolism occurs and no metabolites have as yet been identified.

Biological Half-Life：

The half-life of voglibose is very similar to the one found for metformin and it is reported to be of 4.08 hours.

Mechanism of Action：

Alpha-glucosidase inhibitors are saccharides that act as competitive inhibitors of enzymes needed to digest carbohydrates: specifically alpha-glucosidase enzymes in the brush border of the small intestines. The membrane-bound intestinal alpha-glucosidases hydrolyze oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the small intestine. Acarbose also blocks pancreatic alpha-amylase in addition to inhibiting membrane-bound alpha-glucosidases. Pancreatic alpha-amylase hydrolyzes complex starches to oligosaccharides in the lumen of the small intestine. Inhibition of these enzyme systems reduces the rate of digestion of complex carbohydrates. Less glucose is absorbed because the carbohydrates are not broken down into glucose molecules. In diabetic patients, the short-term effect of these drugs therapies is to decrease current blood glucose levels: the long term effect is a small reduction in hemoglobin-A1c level. (From Drug Therapy in Nursing, 2nd ed)

MeSH Entry Terms：

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

Voglibose Use and Manufacturing

Methods of Manufacturing

III (0.2 g, 0.001 mmol) was added to DMF (8 mL), stirred and dissolved, followed by the addition of 1, 3-dihydroxyacetone (0.3 g, 0.03 mmol), 2N HCl (0.15 mL) and NaBH3CN (0.22 g, 0.004 mol) at 60 °C for 24 h cooled to room temperature, add water (3mL), adjusted to pH=4.0 with 2 Ν HCl, stirred for 30min, 1N NaOH was added to adjust PH = 7.0, the solvent was distilled off under reduced pressure through the UBK resin, followed by elution with water, 2N ammonia, and the eluate was collected and concentrated. After passing through CG50, water: ethanol (6: 4) was eluted and the eluate was collected, and then decolorized by Dowex1 x 2 to give 0.24 g of white powder voglibose, 85percent.To a solution of 6 (483mg, 2.5mmol) in DMF (30mL), 1, 3-dihydroxyacetone (900mg, 10.0mmol) and 2.0M hydrochloric acid (0.50mL) and NaBHThe synthesis of voglibose from the starting material, d-glucose, to compound 1 referred to the previous reports.

Uses

For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications. Used to treat diabetes; anti-diabetic drugs

Computed Properties

Molecular Weight:267.28
XLogP3:-4.1
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:267.13180201
Monoisotopic Mass:267.13180201
Topological Polar Surface Area:154
Heavy Atom Count:18
Complexity:263
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is an oral hypoglycemic drug. It delays the digestion and absorption of sugars and improves postprandial hyperglycemia by inhibiting disaccharide hydrolases (alpha-glucosidase) in the intestine. It has a strong inhibitory effect on maltase and sucrase, but a weak inhibitory effect on alpha-amylase and no inhibitory effect on beta-glucosidase.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Voglibose Capsules
Ingredients	Chemical name: ()-1L-[1(hydroxy),2,4,5/3]-5-[2-hydroxy-1-(hydroxymethyl)ethyl]amino-1-carbon-(hydroxymethyl)-1,2,3,4-cyclohexanetetraol
Indication	Precautions for combined use 1. When using diabetes drugs (such as sulfonamides and sulfonylureas, biguanides, insulin preparations, insulin sensitizers): When using insulin and sulfonylureas together, hypoglycemia has been reported. Therefore, when using the above drugs together, the possibility of hypoglycemia should be considered and the drug should be administered at a low dose with caution. 2. When using diabetes drugs together with drugs that enhance or reduce their hypoglycemic effects: (1) Drugs that enhance the hypoglycemic effect of diabetes drugs [beta-blockers, salicylic acid preparations, monoamine oxidase inhibitors, fibrate hyperlipidemia treatment agents, warfarin, etc.]. (2) Drugs that reduce the hypoglycemic effect of diabetes drugs (epinephrine, adrenocortical hormones, thyroid hormones, etc.). When using the above drugs together with this product, the interactions recorded in the precautions for using diabetes drugs should be noted, and full attention should also be paid to the effects of this product's delayed sugar absorption effect.
Specifications	0.1mg
Manufacturer	Cisen Pharmaceutical Co., Ltd.

Voglibose
Manufacturer	Zhejiang Hisoar Pharmaceutical Co., Ltd.

Voglibose Tablets
Ingredients	The main ingredient of this product is voglibose, and its chemical name is ()-1L-[1(OH),2,4,5/3]-5-[2-hydroxy-1-(hydroxymethyl)ethyl]amino-1-carbon-(hydroxymethyl)-1,2,3,4-cyclohexylfuran. Molecular formula: C10H21NO7, molecular weight: 267.28.
Indication	Precautions for combined use 1. When using diabetes drugs (such as sulfonamides and sulfonylureas, biguanides, insulin preparations, insulin sensitizers) together: When using insulin and sulfonylureas together, there have been reports of hypoglycemia. Therefore, when using the above drugs together, the possibility of hypoglycemia should be considered and the drug should be administered cautiously from a low dose. 2. When using diabetes drugs together with drugs that enhance or reduce their hypoglycemic effects: 1) Drugs that enhance the hypoglycemic effect of diabetes drugs (beta-blockers, salicylic acid preparations, monoamine oxidase inhibitors, fibrate hyperlipidemia treatment agents, warfarin, etc.) 2) Drugs that reduce the hypoglycemic effect of diabetes drugs (epinephrine, adrenocortical hormones, thyroid hormones, etc.) When the above drugs are used together with this product, the interactions recorded in the precautions for using diabetes drugs together should be noted, and full attention should also be paid to the effects of this product's delayed sugar absorption effect.
Specifications	0.2mg
Manufacturer	Chiatai Qingchunbao Pharmaceutical Co., Ltd.

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Registered Holders

JEIL PHARMACEUTICAL CO.,LTD.

South Korea
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