Drug/Small Molecule:
acarbose

Overview

IUPAC Name: (2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4S,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,4-triol
Trade Names: Glucobay; Prandase; Precose
PharmGKB Accession Id: PA448010

Description

An inhibitor of alpha glucosidase that retards the digestion and absorption of carbohydrates in the small intestine and hence reduces the increase in blood-glucose concentrations after a carbohydrate load. It is given orally to non-insulin dependent diabetes mellitus patients where diet modification or oral hypoglycemic agents do not control their condition. (From Martindale The Extra Pharmacopoeia, 31st ed)

Indication

For treatment and management of diabetes type II (used in combination therapy as a second or third line agent)

ATC Therapeutic Category

  • A10BF:Alpha glucosidase inhibitors

Pharmacology and Interactions

Mechanism Of Action

Acarbose reversibly bind to pancreatic alpha-amylase and membrane-bound intestinal alpha-glucoside hydrolases. These enzymes inhibit hydrolysis of complex starches to oligosaccharides in the lumen of the small intestine and hydrolysis of oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the brush border of the small intestine.

Pharmacology

Used to reduce blood gluose in patients with type 2 diabetes. Acarbose is a complex oligosaccharide that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. Acarbose binds to and inhibits alpha amylase and alpha-gluocside hydrolases. In diabetic patients, this enzyme inhibition results in a delayed glucose absorption and a lowering of postprandial hyperglycemia.

Food Interactions

Take with food, at beginning of each meal.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Absorption

Extremely low bioavailability.

Half Life

2 hours

Chemical Properties

Chemical Formula:

C25H43NO18

SMILES Code:

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]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

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

645.6048 / 645.248

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

digoxin Decreased serum levels of digoxin, it is thought that acarbose reduces digoxin absorption.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00284
ChEBI ID:
2376
KEGG Compound ID:
C06802
KEGG Drug ID:
D00216
PubChem Compound ID:
441184
PubChem Substance ID:
7847283

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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