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83480-29-9

83480-29-9 structure
83480-29-9 structure
  • Name: Voglibose
  • Chemical Name: Voglibose
  • CAS Number: 83480-29-9
  • Molecular Formula: C10H21NO7
  • Molecular Weight: 267.276
  • Catalog: API Hormone and endocrine-regulating drugs Pancreatic hormones and other blood sugar regulating drugs
  • Create Date: 2018-06-21 13:10:28
  • Modify Date: 2024-01-02 16:32:05
  • 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].

Name Voglibose
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
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.

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
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

~91%

83480-29-9 structure

83480-29-9

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

~80%

83480-29-9 structure

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

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83480-29-9 structure

83480-29-9

Literature: WO2005/30698 A1, ; Page/Page column 9-10 ;

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83480-29-9 structure

83480-29-9

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