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Acarbose

CAT: 0957-S1271-02Size: 1 gDry Ice: YesHazardous: No
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Description
Acarbose (BAY g 5421, Prandase, Precose, Glucobay, Bay-g 5421) is an inhibitor of intestinal alpha-glucosidase, used to treat type 2 diabetes mellitus.
CAS Number
56180-94-0
Synonyms
BAY g 5421, Prandase, Precose, Glucobay, Bay-g 5421
Target
Carbohydrate Metabolism
Activity
Metabolism
Molecular Formula
C25H43NO18
Storage Conditions
2 years -80 in solvent

Chemical Information

Acarbose

Acarbose is a complex oligosaccharide that acts as an inhibitor of several enzymes responsible for the breakdown of complex carbohydrates in the intestines. It inhibits both pancreatic alpha-amylase and membrane-bound alpha-glucosidases - including intestinal glucoamylase, sucrase, maltase, and isomaltase - which are responsible for the metabolism of complex starches and oligo-, tri-, and disaccharides into absorbable simple sugars. By inhibiting the activity of these enzymes, acarbose limits the absorption of dietary carbohydrates and the subsequent postprandial increase in blood glucose and insulin levels. Acarbose is therefore used in conjunction with diet, exercise, and other pharmacotherapies for the management of blood sugar levels in patients with type 2 diabetes. Acarbose is one of only two approved alpha-glucosidase inhibitors (the other being [miglitol]), receiving its first FDA approval in 1995 under the brand name Precose (since discontinued). This class of antidiabetic therapy is not widely used due to their relatively modest impact on A1c, their requirement for thrice-daily dosing, and the potential for significant gastrointestinal adverse effects.

CAS Number56180-94-0
PubChem CID9811704
IUPAC Name(2R,3R,4R,5R)-4-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,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-2,3,5,6-tetrahydroxyhexanal
Molecular FormulaC25H43NO18
Molecular Weight645.6
XLogP-8.8
Topological Polar Surface Area329
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count19
Rotatable Bond Count13
Heavy Atom Count44
Formal Charge0
Complexity945
SMILES
C[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]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)CO)O)O)N[C@H]3C=C([C@H]([C@@H]([C@H]3O)O)O)CO
InChI
InChI=1S/C25H43NO18/c1-7-13(26-9-2-8(3-27)14(33)18(37)15(9)34)17(36)20(39)24(41-7)44-23-12(6-30)42-25(21(40)19(23)38)43-22(11(32)5-29)16(35)10(31)4-28/h2,4,7,9-27,29-40H,3,5-6H2,1H3/t7-,9+,10+,11-,12-,13-,14-,15+,16-,17+,18+,19-,20-,21-,22-,23-,24-,25-/m1/s1
InChIKey
CEMXHAPUFJOOSV-XGWNLRGSSA-N
Chemical Structure
2D Structure
2D structure of Acarbose
CAS: 56180-94-0
CID: 9811704
Formula: C25H43NO18
MW: 645.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight645.6
XLogP3-8.8
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count19
Rotatable Bond Count13
Exact Mass645.24801352
Monoisotopic Mass645.24801352
Topological Polar Surface Area329 Ų
Heavy Atom Count44
Formal Charge0
Complexity945
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
A2431-1000Acarbose

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