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83480-29-9, Voglibose, CAS: 83480-29-9

83480-29-9, Voglibose,
CAS: 83480-29-9
C10H21NO7 / 267.28
MFCD00865496

Voglibose , 伏格列波糖

Voglibose is a competitive α-glucosidase inhibitor (IC50 = 5.6 µM) that was first isolated from S. hygroscopicus. It has been shown to delay the absorption and digestion of dietary polysaccharides by reversibly inhibiting digestive enzymes such as maltase, isomaltase, and sucrase with IC50 values of 0.18, 5.2, and 0.37 µM, respectively. Voglibose is also reported to increase glucagon-like peptide 1 release. In clinical trials, voglibose has been used to inhibit postprandial hyperglycemia associated with diabetes without cardiovascular complications.

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, also known as basen or glustat, belongs to the class of organic compounds known as aminocyclitols. These are cyclitols with at least one hydroxyl group replace by an amino group. Voglibose is a drug which is used for the treatment of diabetes. it is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications. Voglibose is soluble (in water) and a very weakly acidic compound (based on its pKa). Voglibose has been detected in multiple biofluids, such as urine and blood.

Voglibose is an organic molecular entity.

Voglibose is a competitive inhibitor of α-glucosidase used for the control of blood sugar levels in patients with type 2 diabetes mellitus. The compound binds reversibly to intestinal carbohydrate-active digestive enzymes with α-glucosidase activity, inhibits breakdown of complex sugars and consequently delays the absorption of glucose into blood.

Title: Voglibose

CAS Registry Number: 83480-29-9

CAS Name: 3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epiinositol

Additional Names: N-(1,3-dihydroxy-2-propyl)valiolamine

Manufacturers' Codes: AO-128

Trademarks: Basen (Takeda)

Molecular Formula: C10H21NO7

Molecular Weight: 267.28

Percent Composition: C 44.94%, H 7.92%, N 5.24%, O 41.90%

Literature References: a-Glucosidase inhibitor. Prepn: S. Horii et al., EP 56194; eidem, US 4701559 (1982, 1987 both to Takeda); and structure-activity study: eidem et al., J. Med. Chem. 29, 1038 (1986). Synthesis: H. Fukase, S. Horii, J. Org. Chem. 57, 3651 (1992). Enzyme inhibition and pharmacology: T. Matsuo et al., Am. J. Clin. Nutr. 55, 314S (1992). Clinical pharmacology: B. Göke et al., Digestion 56, 493 (1995). Clinical evaluation in hyperinsulinemia: K. Shinozaki et al., Metabolism 45, 731 (1996).

Properties: Colorless crystals, mp 162-163°. [a]D25 +26.2° (c = 1 in water).

Melting point: mp 162-163°

Optical Rotation: [a]D25 +26.2° (c = 1 in water)

Therap-Cat: Antidiabetic.

Keywords: Antidiabetic; a-Glucosidase Inhibitor.

CAS Number83480-29-9
Product NameVoglibose
IUPAC Name(1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetraol
Molecular FormulaC10H21NO7
Molecular Weight267.28 g/mol
InChIInChI=1S/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
InChI KeyFZNCGRZWXLXZSZ-CIQUZCHMSA-N
SMILESO[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](NC(CO)CO)C1
SolubilitySoluble in DMSO, not in water
Synonyms3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol, Basen, N-(1,3-dihydroxy-2-propyl)valiolamine, voglibose
Canonical SMILESC1C(C(C(C(C1(CO)O)O)O)O)NC(CO)CO
Isomeric SMILESC1[C@@H]([C@@H]([C@H]([C@@H]([C@]1(CO)O)O)O)O)NC(CO)CO


CAS No: 83480-29-9 Synonyms: 3,4-Dideoxy-[2-hydroxy-1-(hydroxyethyl)ethyl] amino-1-C-(hydroxynethyl)-1,2,3,4-cyclohexaneterol3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epiinositol MDL No: MFCD00865496 Chemical Formula: C10H21NO7 Molecular Weight: 267.28

COA:

Name: Voglibose   CAS: 83480-29-9     M.F.: C10H21NO7  M.W.: 267.28    

Items

Standards

Results

Appearance

White crystalline powder

Positive

Solubility

Very slightly soluble in water, freely soluble in acetic acid, slightly soluble in methanol

Complies

NMR and MS

Should comply

Complies

Identification

IR and HPLC

Positive

M.P.

163 ~168

164 ~166

Specific rotation

(0.1% in 0.1mol/L HCl)

+45o ~ +48o

+47.6o

pH (10%)

9.8 ~ 10.4

10.2

Heavy metal

Max. 10ppm

Complies

Water

Max. 0.2%

0.1%

Residue On Ignition

Max. 0.1%

0.02%

Total impurities

Max. 0.2%

0.08

Any impurity

Max. 0.1%

Complies

Assay

99.5% ~ 101%

99.8%

References:

1. Shinozaki K, et al., Metabolism 1996, 45, 731


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