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G0639

Sigma-Aldrich

Glybenclamide

≥99% (HPLC)

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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
PubChem Substance ID:
57654199
NACRES:
NA.77

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)

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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.

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

Regulatory Information

涉药品监管产品

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Potential hypoglycemic effects of Chlorella in streptozotocin-induced diabetic mice
Jong-Yuh C and Mei-Fen S
Life Sciences, 77(9), 980-990 (2005)
ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats
Ortega FJ, et al.
Experimental neurology, 235(1), 282-296 (2012)
The effects of levosimendan and glibenclamide on circulatory and metabolic variables in a canine model of acute hypoxia
Schwarte LA, et al.
Intensive Care Medicine, 37(4), 701-710 (2011)
Glybenclamide: an antidiabetic with in vivo antithrombotic activity
Ting HJ and Khasawneh FT
European Journal of Pharmacology, 649(1-3), 249-254 (2010)
Hypoglycaemic Effect of Glibenclamide: A Critical Study on the Basis of Creatinine and Lipid Peroxidation Status of Streptozotocin-induced Diabetic Rat
Sreejesh PG, et al.
Indian Journal of Pharmaceutical Sciences, 79(5), 768-777 (2017)
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