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Key Documents

G0639

Sigma-Aldrich

Glibenclamide

≥99% (HPLC)

Sinonimo/i:

5-cloro-N-[4-(cicloesilureidosolfonil)fenetil]-2-metossibenzamide, Gliburide, N-p-[2-(5-cloro-2-metossibenzamido)etil]benzenesolfonil-N′-cicloesilurea

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About This Item

Formula empirica (notazione di Hill):
C23H28ClN3O5S
Numero CAS:
Peso molecolare:
494.00
Numero CE:
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Saggio

≥99% (HPLC)

Solubilità

ethanol: 2 mg/mL
DMSO: soluble
H2O: insoluble

Ideatore

Roche

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Informazioni sul gene

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Applicazioni

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

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Indicazioni di pericolo

Consigli di prudenza

Classi di pericolo

Aquatic Chronic 4

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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Glibenclamide impurity A European Pharmacopoeia (EP) Reference Standard

G0325010

Glibenclamide impurity A

Repaglinide ≥98% (HPLC), solid

Sigma-Aldrich

R9028

Repaglinide

Glipizide solid

Sigma-Aldrich

G117

Glipizide

Nateglinide ≥98% (HPLC), solid

Sigma-Aldrich

N3538

Nateglinide

Tolbutamide analytical standard

Supelco

T0891

Tolbutamide

Supelco

Supelco

C1290

Chlorpropamide

Gliclazide powder, ≥98%

Sigma-Aldrich

G2167

Gliclazide

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)
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)
ATP-dependent potassium channel blockade strengthens microglial neuroprotection after hypoxia-ischemia in rats
Ortega FJ, et al.
Experimental neurology, 235(1), 282-296 (2012)
Potential hypoglycemic effects of Chlorella in streptozotocin-induced diabetic mice
Jong-Yuh C and Mei-Fen S
Life Sciences, 77(9), 980-990 (2005)

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