Acarbose

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Description

Acarbose is an inhibitor of intestinal alpha-glucosidase, used to treat type 2 diabetes mellitus.

CAS Number

56180-94-0

Stability

≥ 2 years

Purity

>98% (HPLC)

Weight

645.6

Molecular Formula

C25H43NO18

Notes

Research use only, not for human use.

Receptor

Α-glucosidase

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 Number	56180-94-0
PubChem CID	9811704
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 Formula	C25H43NO18
Molecular Weight	645.6
XLogP	-8.8
Topological Polar Surface Area	329
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	13
Heavy Atom Count	44
Formal Charge	0
Complexity	945

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

CAS: 56180-94-0

CID: 9811704

Formula: C25H43NO18

MW: 645.6

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	645.6
XLogP3	-8.8
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	13
Exact Mass	645.24801352
Monoisotopic Mass	645.24801352
Topological Polar Surface Area	329 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	945
Isotope Atom Count	0
Defined Atom Stereocenter Count	18
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
A2431-1000	Acarbose

Acarbose

Chemical Information

Alternative Products

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