Acarbose

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of acarbose
General
Non-proprietary name Acarbose
other names

O -4,6-dideoxy-4 - {[(1 S , 4 R , 5 S , 6 S ) -4,5,6-trihydroxy-3- (hydroxymethyl) -2-cyclohexen-1-yl] amino} -α- D -glucopyranosyl- (1,4) - O -α- D -glucopyranosyl- (1,4) - D -glucopyranose ( IUPAC )

Molecular formula C 25 H 43 NO 18
Brief description

white to yellowish, amorphous, hygroscopic powder

External identifiers / databases
CAS number 56180-94-0
EC number 260-030-7
ECHA InfoCard 100.054.555
PubChem 444254
DrugBank DB00284
Wikidata Q338005
Drug information
ATC code

A10 BF01

Drug class

Antidiabetic drugs

Mechanism of action

Inhibition of the enzyme α-glucosidase, thereby reducing the breakdown of multiple sugars, resulting in less glucose absorption

properties
Molar mass 645.61 g mol −1
solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

5000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acarbose is a sugar and is classified as a pseudotetrasaccharide due to its structure . As a medicinal substance , it is used as an additional therapy in the treatment of diabetes mellitus as a so-called oral antidiabetic in connection with diet. The substance is obtained from bacteria of the genus Actinoplanes or from Streptomyces glaucescens.

It was developed as a remedy for diabetes by Walter Puls at Bayer (trade name: Glucobay ).

effect

Acarbose, an α-glucosidase inhibitor, inhibits α-glucosidase , an enzyme that catalyzes the hydrolysis of oligo- , tri- and disaccharides to glucose and other monosaccharides in the intestine . This reduces an increase in blood sugar levels after meals (postprandial). Because of this mode of action, acarbose is suitable for the therapy of type 2 diabetes mellitus.

Pharmacokinetics

Acarbose has a systemic bioavailability of 0.5 to 2 percent. Most of it remains in the lumen of the gastrointestinal tract . After digestion by intestinal bacteria, up to 35 percent can be absorbed in the form of sugar units. Only 2 percent is excreted through the kidneys. 51 percent can be found in the faeces . The elimination half-life of acarbose is approx. 2 hours.

Side effects

Under the action of acarbose, starch escapes small intestinal digestion. In the large intestine, this starch is fermented with increased butyric acid formation . This leads to the typical side effects , which significantly limit the use, such as flatulence , bowel noises, diarrhea , stomach pain and occasionally nausea.

Other effects

In addition to its use as a drug, acarbose was recognized in 1996 as having the potential to be used as an effective prophylaxis against tooth decay . This did not result in any clinical relevance.

Contraindications

Acarbose should not be administered in severe renal insufficiency or severe liver dysfunction.

Trade names

Acarbose is commercially available in Germany, Austria and Switzerland under the name Glucobay and under the generic name.

literature

  • Richard Daikeler, Götz Use, Sylke Waibel: Diabetes. Evidence-based diagnosis and therapy. 10th edition. Kitteltaschenbuch, Sinsheim 2015, ISBN 978-3-00-050903-2 , p. 156.

Individual evidence

  1. ↑ a b c d e data sheet ACARBOSE CRS (PDF) at EDQM , accessed on April 14, 2009.
  2. ↑ a b Acarbose data sheet from Sigma-Aldrich , accessed on October 24, 2016 ( PDF ).
  3. ↑ a b c Keyword Acarbose In: Hans Zoebelein (Ed.): Dictionary of Renewable Resources. 2nd edition, Wiley-VCH, Weinheim and New York 1996; Page 1. ISBN 3-527-30114-3 .
  4. ↑ Bayer website on research success .
  5. ↑ ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 157.