Glibenclamide

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Structural formula
Structural formula of glibenclamid
General
Non-proprietary name Glibenclamide
other names
  • 5-chloro- N - (2- {4 - [(cyclohexylcarbamoyl) sulfamoyl] phenyl} ethyl) -2-methoxybenzenecarboxamide ( IUPAC )
  • 1 - [(4- {2 - [(5-chloro-2-methoxybenzoyl) amino] ethyl} phenyl) sulfonyl] -3-cyclohexylurea ( Pharmacopoeia )
Molecular formula C 23 H 28 ClN 3 O 5 S
External identifiers / databases
CAS number 10238-21-8
EC number 233-570-6
ECHA InfoCard 100.030.505
PubChem 3488
ChemSpider 3368
DrugBank DB01016
Wikidata Q420626
Drug information
ATC code

A10 BB01

Drug class

Antidiabetic drugs , sulfonylureas

Mechanism of action

Potassium channel blockers

properties
Molar mass 494.00 g · mol -1
Melting point
  • 171–175 ° C ( polymorph I)
  • 151 ° C (polymorph II)
  • 153 ° C (polymorph III)
pK s value

5.3

solubility
  • practically insoluble in water (2.3 ± 0.3 mg l −1 , at pH 6.5)
  • soluble in ethanol (5 g / l), DMSO (25 g / l), chloroform (1:36), methanol (1: 250) and DMF
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
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Glibenclamide is a chemical compound from the group of sulfonylureas , which is used in medicine as an antidiabetic . It is effective orally and causes an increased release of insulin from the β-cells of the pancreas .

If it is possible to lower blood sugar effectively, the risk of the long-term effects of diabetes mellitus is also reduced with glibenclamide . Because of its undesirable effects, however, metformin is now the first choice of active ingredient, although it can be combined with glibenclamide.

indication

Glibenclamide is indicated for non-insulin-dependent type 2 diabetes mellitus when other measures such as diet, weight reduction and physical activity have not led to adequate control of the blood sugar.

Working principle

Like other sulfonylureas, glibenclamide blocks potassium channels in the β-cells and thus inhibits the outflow of these ions . This leads to a depolarization and thus to the opening of voltage-controlled calcium channels ; Calcium ions increasingly flow into the cell. This activates enzymes that cause insulin to be released. For glibenclamide to work, the body must have the ability to secrete insulin.

unwanted effects

The blood sugar lowering effect of glibenclamide sets in quickly and can last for up to 24 hours. This fact must be taken into account in the dosage and when monitoring the blood sugar level , since a relative overdose (e.g. with irregular food intake) can lead to hypoglycaemia . The hypoglycemic coma (colloquially "hypoglycemic shock" or "sugar shock") is feared. The weight normalization of overweight diabetics is problematic, since glibenclamide has an appetite-stimulating effect (insulin release).

Glibenclamide impairs ischemic preconditioning in the heart muscle, which can lead to more extensive myocardial infarction when the myocardial oxygen supply is interrupted. On the other hand, cardioprotective effects such as an antiarrhythmic effect have also been described.

Contraindications

Glibenclamide is contraindicated in the case of severe renal insufficiency and severe liver dysfunction.

Neonatal diabetes

In May 2018, Glibenclamid was approved under the name Amglidia (AMMTek) in the EU for the treatment of neonatal diabetes in newborns, infants and children, a rare disease . For this group of patients, the drug is available as an orally administrable suspension (0.6 mg / ml or 6 mg / ml), which is dosed with an oral syringe.

Trivia

Elfriede Blauensteiner , who went down in Austrian criminal history as the “black widow”, used, among other things, Euglucon (glibenclamide tablets) for her murders .

Trade names

Monopreparations
Amglidia (EU), Daonil (A, CH), Euglucon N (D, A), Gliben CT (D), Glibenorm (CH), Glibesifar (CH), Glucobe (A), Normoglucon (A), Maninil (D ), Melix (CH), Semi-Daonil (CH), Semi-Euglucon (D), numerous generics (D, A, CH) Combination products
Glucovance (A)

Web links

Individual evidence

  1. ↑ a b c Young-Tack Sohn, Bo-Young Um: Dissolution of Glibenclamide Polymorphs . In:, 27, 1997, pp. 233-239.
  2. ↑ a b c M.A. Hassan, M. Sheikh Salem, MK Al-Hindawi: Preparation and characterization of a new polymorphic form and a solvate of glibenclamide . In: Acta Pharm. Hung. , 67, 1997, pp. 81-88.
  3. ↑ a b c d e f g Data sheet Glybenzcyclamide, 99% from AlfaAesar, accessed on December 26, 2019 ( PDF )(JavaScript required) .
  4. ^ Carsten jewelry, Bernd Engels, Tanja Schirmeister, Reinhold Fink: Chemistry for medical professionals . Pearson Studium, ISBN 978-3-8273-7286-4 , p. 654.
  5. ↑ K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs . In: Pharm Res , 26, 2009, pp. 2093-2100. doi: 10.1007 / s11095-009-9921-3 .
  6. ↑ Richard Daikeler, idols Use, Sylke Waibel: diabetes. Evidence-based diagnosis and therapy. 10th edition. Kitteltaschenbuch, Sinsheim 2015, ISBN 978-3-00-050903-2 , p. 168.
  7. ↑ EPAR Amglidia .
This text is based in whole or in part on the entry sulfonylurea in Flexikon , a wiki of the DocCheck company . The takeover took place on March 1, 2007 under the then valid GNU license for free documentation .