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56180-94-0, Acarbose, CAS:56180-94-0

56180-94-0, Acarbose,
CAS:56180-94-0
C25H43NO18 / 645.60
MFCD00869592

阿卡波糖, Acarbose

Competitive, reversible inhibitor of α-glucosidases used for the control of postprandial hyperglycaemia in patients with type 2 diabetes mellitus. It inhibits digestive enzymes with α-glucosidase activity, which breakdown complex sugars to absorbable monosaccharides. It also reduces the levels of glycated haemoglobin (HbA1c). 

Acarbose is the first identified α-glucosidase inhibitor. It has been shown to delay the absorption and digestion of dietary polysaccharides by reversibly inhibiting digestive enzymes such as maltase and sucrase with IC50 values of 0.16 and 2.9 µM, respectively. It has also been shown to bind to phosphorylase kinase, potentiating its activity. In clinical trials, acarbose has been used to inhibit postprandial hyperglycemia associated with diabetes without cardiovascular complications.

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Acarbose is an oral antidiabetic drug, a glucosidase inhibitor used in the management of non-insulin-dependent diabetes mellitus (NIDDM).

Acarbose is a pseudotetrasaccharide and inhibitor of alpha-glucosidase and pancreatic alpha-amylase with antihyperglycemic activity. Acarbose 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. In addition, acarbose inhibits pancreatic alpha-amylase which hydrolyzes complex starches to oligosaccharides in the small intestines.

Acarbose is an alpha glucosidase inhibitor which decreases intestinal absorption of carbohydrates and is used as an adjunctive therapy in the management of type 2 diabetes. Acarbose has been linked to rare instances of clinically apparent acute liver injury.

Acarbose, also known as bay g 5421 or glumida, belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4, 5- and 4, 6-disubstituted 2-deoxystreptamines. Acarbose is soluble (in water) and a very weakly acidic compound (based on its pKa). Acarbose has been detected in multiple biofluids, such as urine and blood. Within the cell, acarbose is primarily located in the cytoplasm.

Title: Acarbose

CAS Registry Number: 56180-94-0

CAS Name: O-4,6-Dideoxy-4-[[[1S-(1a,4a,5b,6a)]-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-a-D-glucopyranosyl-(1®4)-O-a-D-glucopyranosyl-(1®4)-D-glucose

Additional Names: 4'',6''-dideoxy-4''-[(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino]maltotriose

Manufacturers' Codes: Bay g 5421

Trademarks: Glucobay (Bayer); Prandase (Bayer); Precose (Bayer)

Molecular Formula: C25H43NO18

Molecular Weight: 645.60

Percent Composition: C 46.51%, H 6.71%, N 2.17%, O 44.61%

Literature References: Pseudotetrasaccharide containing an unsaturated cyclitol moiety. An a-glucosidase inhibitor that reduces sugar absorption in the gastrointestinal tract. Isoln from strains of Actinoplanes: W. Frommer et al., DE 2347782; eidem, US 4062950 (1975, 1977 both to Bayer). Total synthesis: S. Ogawa, Y. Shibata, Chem. Commun. 1988, 605; eidem, Carbohydr. Res. 189, 309 (1989). Biosynthetic studies: U. Degwert et al., J. Antibiot. 40, 855 (1987). Glucosidase inhibition studies: D. D. Schmidt et al., Naturwissenschaften 64, 535 (1977); W. Puls et al., ibid. 536. Use in treatment of diabetic adults: D. Sailor, G. Roder, Arzneim.-Forsch. 30, 2182 (1980); H. Laube et al., ibid. 1154. Long-term study in sulfonylurea-treated diabetics: H. Vierhapper et al., Diabetologia 20, 586 (1981). Potential use in prophylaxis of dental caries: N. E. Fiehn, D. Moe, Scand. J. Dent. Res. 90, 124 (1982). Review of pharmacodynamics, pharmacokinetics and therapeutic potential: S. P. Clissold, C. Edwards, Drugs 35, 214-243 (1988).

Properties: Amorphous powder. [a]D18 +165° (c = 0.4 in water).

Optical Rotation: [a]D18 +165° (c = 0.4 in water)

Therap-Cat: Antidiabetic.

Keywords: Antidiabetic; a-Glucosidase Inhibitor.

CAS Number56180-94-0
Product NameAcarbose
IUPAC Name(3R,4R,6R)-5-[(3R,4R,6R)-5-[(3R,4S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
Molecular FormulaC25H43NO18
Molecular Weight645.60 g/mol
InChIInChI=1S/C25H43NO18/c1-6-11(26-8-2-7(3-27)12(30)15(33)13(8)31)14(32)19(37)24(40-6)43-22-10(5-29)42-25(20(38)17(22)35)44-21-9(4-28)41-23(39)18(36)16(21)34/h2,6,8-39H,3-5H2,1H3/t6-,8+,9-,10-,11?,12-,13+,14+,15+,16-,17-,18-,19-,20-,21?,22?,23?,24?,25?/m1/s1
InChI KeyCEMXHAPUFJOOSV-XGWNLRGSSA-N
SMILESCC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO
SolubilityIn water, 1.0X10+6 mg/L /miscible/ at 25 °C (est)
1.48e+02 g/L
SynonymsAcarbose, Bay g 5421, Glucobay, Glucor, Glumida, Prandase, Precose
Canonical SMILESCC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C=C(C(C(C4O)O)O)CO
Isomeric SMILESC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@@H]([C@@H]([C@H]2O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O)CO)CO)O)O)N[C@H]4C=C([C@@H]([C@@H]([C@H]4O)O)O)CO


CAS No: 56180-94-0 Synonyms: 4'',6''-Dideoxy-4''-([1S]-[1,4,6/5]-4,5,6-trihydroxy-3-hydroxymethyl-2-yclohexenylamino)-maltotriose MDL No: MFCD00869592 Chemical Formula: C25H43NO18 Molecular Weight: 645.605
References: 1. Sailor D, et al., Arzneim.-Forsch. 1982, 30, p2182


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