Voglibose

Names

[ Name ]:
Voglibose

[Synonym ]:
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

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]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[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.

[Related Small Molecules]

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

MSDS

Click to get detail MSDS

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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...

Related Compounds

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