356310

Glyburide

A sulfonylurea that selectively blocks ATP-sensitive K⁺ channels.

• Synonym(e): Glyburide, Glybenclamide
• Empirische Formel (Hill-System): C₂₃H₂₈ClN₃O₅S
• CAS-Nummer: 10238-21-8
• Molekulargewicht: 494.00
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00056625
• Assay: ≥98% (TLC)
• Form: solid
• Storage condition: OK to freeze

Eigenschaften

• Quality Segment: 100
• description: Merck USA index - 14, 4478
• assay: ≥98% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 25 mg/mL, ethanol: 5 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• SMILES string: [S](=O)(=O)(NC(=O)NC3CCCCC3)c1ccc(cc1)CCNC(=O)c2c(ccc(c2)Cl)OC
• InChI: 1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
• InChI key: ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Beschreibung

General description

A sulfonylurea that selectively blocks ATP-sensitive K⁺ channels. Reduced K⁺ conductance causes membrane depolarization and influx of Ca²⁺ through voltage sensitive Ca²⁺ channels. Blocks vascular smooth muscle relaxation produced by K_ATP channel openers. Inhibits the vasorelaxing effects of nitric oxide.

Antidiabetic sulfonylurea that selectively blocks ATP-sensitive K⁺ channels. Reduced K⁺ conductance causes membrane depolarization and influx of Ca²⁺ through voltage sensitive Ca²⁺ channels. Blocks vascular smooth muscle relaxation produced by K_ATP channel openers. High-affinity binding sites are widely distributed and have been identified in the cardiovascular system, the central nervous system, and pancreatic β-cells. In cultured cells, glyburide enhances insulin action and stimulates the synthesis of glucose transporters. Displays large potency difference in action on pancreatic tissue (IC₅₀ in nM range) and vascular tissue (IC₅₀ in µM range).

Biochem/physiol Actions

Cell permeable: no

Primary Target
ATP-sensitive K+ channels

Product does not compete with ATP.

Reversible: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Holzmann, S., et al. 1992. Eur. J. Pharmacol.215, 1.
Rabuazzo, A.M., et al. 1992. Endocrinology131, 1815.
Miller, J.A., et al. 1991. J. Pharmacol. Exp. Ther.256, 358.
Jacobs, D.R., et al. 1989. Diabetes 38, 205.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• hcodes: H413
• pcodes: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable