G0639

Glybenclamide

≥99% (HPLC)

• Synonym(s): 5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide, Glyburide, N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N′-cyclohexylurea
• Empirical Formula (Hill Notation): C₂₃H₂₈ClN₃O₅S
• CAS Number: 10238-21-8
• Molecular Weight: 494.00
• EC Number: 233-570-6
• MDL number: MFCD00056625
• UNSPSC Code: 12352200
• PubChem Substance ID: 57654199
• NACRES: NA.77

Properties

• Assay: ≥99% (HPLC)
• solubility: ethanol: 2 mg/mL; DMSO: soluble; H₂O: insoluble
• originator: Roche
• storage temp.: 2-8°C
• SMILES string: COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3
• 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
• Gene Information: human ... ABCC8(6833) , KCNH2(3757) , KCNJ1(3758) , KCNJ11(3767) ; rat ... Kcnj1(24521)

Description

Application

Glybenclamide has been used:

• as a positive control oral hypoglycemic drug to study the hypoglycemic effects of Chlorella in streptozotocin-induced diabetic mice
• as a K+ATP channel antagonist in canine with induced acute hypoxia
• as an inhibitor of cystic fibrosis transmembrane conductance regulator (CFTR) channel in fetal distal lung epithelial (FDLE) cells

Biochem/physiol Actions

Glybenclamide is a sulfonylurea class of antidiabetic drug used in the treatment of type 2 diabetes mellitus. It has benzamide moiety and stimulates pancreatic β cells to produce insulin resulting in a hypoglycemic effect. It selectively blocks ATP-sensitive K⁺ channels in the brain with high-affinity binding sites and elicits cardiovascular effects. It may be a potential therapeutic for thromboembolic disorders due to its in vivo antiplatelet functionality. Glybenclamide traverses to the ischemic brain and provides neuroprotection especially during the early stages of stroke.

Selectively blocks ATP-sensitive K⁺ channels; high affinity binding sites found in brain, pancreatic β cells, and cardiovascular system.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Chloride Channels and Potassium Channels pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• Hazard Statements: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves