Voglibose

Modify Date: 2024-01-02 16:32:05

Voglibose Structure
Voglibose structure
 Common Name Voglibose
CAS Number 83480-29-9 Molecular Weight 267.276
Density 1.6±0.1 g/cm3 Boiling Point 601.9±55.0 °C at 760 mmHg
Molecular Formula C10H21NO7 Melting Point 162-163ºC
MSDS Chinese USA Flash Point 274.1±22.1 °C

 Use of Voglibose


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 sucrose and maltose [1]. Voglibose (0.2 mg/kg) completely inhibits the insulin response to sucrose in rats. Voglibose (0.2 mg/kg) reduces the carbohydrate-induced increase in blood glucose in rats. Voglibose (0.2 mg/kg) reduces the carbohydrate-induced increase in blood glucose without causing sustained hypoglycemia in both normal and neonatal streptozotocin-induced diabetic rats [2]. Voglibose (0.001%) treatment increases GLP-1 secretion (Voglibose alone, 1.6-fold; Alogliptin plus Voglibose, 1.5-fold), while it decreases plasma glucose-dependent insulinotropic polypeptide (GIP) (Voglibose alone, 30%; Alogliptin plus voglibose, 29%) in prediabetic db/db mice after 3 weeks. Voglibose (0.001%) treatment decreases plasma DPP-4 activity by 15% in prediabetic db/db mice. Voglibose (0.001%) treatment increases plasma insulin by 1.8-fold and decreases plasma glucagon by 8% in prediabetic db/db mice [3].

 Names

Name Voglibose
Synonym More Synonyms

 Voglibose Biological Activity

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 sucrose and maltose [1]. Voglibose (0.2 mg/kg) completely inhibits the insulin response to sucrose in rats. Voglibose (0.2 mg/kg) reduces the carbohydrate-induced increase in blood glucose in rats. Voglibose (0.2 mg/kg) reduces the carbohydrate-induced increase in blood glucose without causing sustained hypoglycemia in both normal and neonatal streptozotocin-induced diabetic rats [2]. Voglibose (0.001%) treatment increases GLP-1 secretion (Voglibose alone, 1.6-fold; Alogliptin plus Voglibose, 1.5-fold), while it decreases plasma glucose-dependent insulinotropic polypeptide (GIP) (Voglibose alone, 30%; Alogliptin plus voglibose, 29%) in prediabetic db/db mice after 3 weeks. Voglibose (0.001%) treatment decreases plasma DPP-4 activity by 15% in prediabetic db/db mice. Voglibose (0.001%) treatment increases plasma insulin by 1.8-fold and decreases plasma glucagon by 8% in prediabetic db/db mice [3].
Related Catalog
References

[1]. Chen, X., Y. Zheng, and Y. Shen, Voglibose (Basen, AO-128), one of the most important alpha-glucosidase inhibitors. Curr Med Chem, 2006. 13(1): p. 109-16.

[2]. Ikenoue, T., et al., Effect of a new hypoglycemic agent, A-4166 [(-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine], on postprandial blood glucose excursion: comparison with voglibose and glibenclamide. Biol Pharm Bull, 1997. 20(4): p. 354-9.

[3]. Moritoh, Y., K. Takeuchi, and M. Hazama, Combination treatment with alogliptin and voglibose increases active GLP-1 circulation, prevents the development of diabetes and preserves pancreatic beta-cells in prediabetic db/db mice. Diabetes Obes Metab, 2010. 12(3): p. 224-33.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 601.9±55.0 °C at 760 mmHg
Melting Point 162-163ºC
Molecular Formula C10H21NO7
Molecular Weight 267.276
Flash Point 274.1±22.1 °C
Exact Mass 267.131805
PSA 153.64000
LogP -2.36
Vapour Pressure 0.0±3.9 mmHg at 25°C
Index of Refraction 1.636
Storage condition Store at -20°C

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi: Irritant;
Risk Phrases R20/21/22
Safety Phrases S36/37
RIDADR NONH for all modes of transport
RTECS NM7524600

 Synthetic Route

Tetrabenzyl voglibose structure

Tetrabenzyl vog...

CAS#:115250-39-0

~91%

Voglibose Structure

Voglibose

CAS#:83480-29-9

Literature: Fukase; Horii Journal of Organic Chemistry, 1992 , vol. 57, # 13 p. 3651 - 3658
1,3-Dihydroxyacetone structure

1,3-Dihydroxyacetone

CAS#:96-26-4

Valiolamine structure

Valiolamine

CAS#:83465-22-9

~80%

Voglibose Structure

Voglibose

CAS#:83480-29-9

Literature: Ji, Li; Zhang, Ding-Feng; Zhao, Qian; Hu, San-Ming; Qian, Chao; Chen, Xin-Zhi Tetrahedron, 2013 , vol. 69, # 34 p. 7031 - 7037
voglibose hydrochloride structure

voglibose hydro...

CAS#:849419-34-7

~%

Voglibose Structure

Voglibose

CAS#:83480-29-9

Literature: WO2005/30698 A1, ; Page/Page column 9-10 ;
(2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone structure

(2R,3S,4S,5S)-5...

CAS#:115250-38-9

~%

Voglibose Structure

Voglibose

CAS#:83480-29-9

Literature: Journal of Organic Chemistry, , vol. 57, # 13 p. 3651 - 3658

 Articles35

More Articles
Intensive glucose lowering in cardiovascular risk management - unsolved questions - .

Circ. J. 76(3) , 593-5, (2012)

Effects of voglibose and nateglinide on glycemic status and coronary atherosclerosis in early-stage diabetic patients.

Circ. J. 76(3) , 712-20, (2012)

Postprandial hyperglycemia and hyperinsulinemia have been considered as important determinants for the development of atherosclerosis. However, it remains to be elucidated whether correction of the po...

Effect of voglibose on the pharmacokinetics of metformin in healthy Korean subjects.

Int. J. Clin. Pharmacol. Ther. 52(11) , 1005-11, (2014)

The objective of this study was to evaluate the effects of voglibose on the pharmacokinetics of metformin.A randomized, open-label, two-way crossover study with a 7-day washout period was conducted. A...

 Synonyms

Beigrace
Jumeal
Voglibose
Glustat
(1S,2S,3R,4S,5S)-5-[(1,3-Dihydroxy-2-propanyl)amino]-1-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol
Voglibose (JP15/USAN)
Basen
Voglistat
3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epiinositol
AO 128
MFCD00865496
1,2,3,4-Cyclohexanetetrol, 5-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-1-(hydroxymethyl)-, (1S,2S,3R,4S,5S)-
(1S,2S,3R,4S,5S)-5-[(1,3-Dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
(1S,2S,3R,4S,5S)-5-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino}-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
N-(1,3-Dihydroxy-2-propyl)valiolamine
(1S,2S,3R,4S,5S)-5-[(1,3-Dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexan-1,2,3,4-tetrol
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