Glibenclamide
Synonym(s):5-Chloro-N-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide;Glybenclamide;Glyburide;Glyburide - CAS 10238-21-8 - Calbiochem;N-p-[2-(5-Chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-N′-cyclohexylurea
- CAS NO.:10238-21-8
- Empirical Formula: C23H28ClN3O5S
- Molecular Weight: 494
- MDL number: MFCD00056625
- EINECS: 233-570-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-08-15 17:37:19
What is Glibenclamide?
Absorption
Elderly patients taking glyburide reached a Cmax of 211-315ng/mL with a Tmax of 0.9-1.0h, while younger patients reached a Cmax of 144-302ng/mL with a Tmax of 1.3-3.0h. Patients taking glyburide have and AUC of 348ng*h/mL.
Toxicity
The oral LD50 in rats is >3200mg/kg, in mice is >1500mg/kg, in rabbits is >10,000mg/kg, and in guinea pigs is >1500mg/kg.
Patients experiencing an overdose may present with hypoglycemia. Mild hypoglycemia should be treated with oral glucose and adjustments to drug doses or meal schedules. Severe hypoglycemia may present with coma, seizure, and neurological impairment. This should be treated immediately in hospital with intravenous glucose and monitoring for 24-48 hours.
Description
Glyburide (10238-21-8) is a second generation oral hypoglycemic agent. Acts via ATP-dependent K+ channel (Kir6, KATP) block.1?Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Glyburide also inhibits recombinant CFTR Cl- channels with an IC50 of 20 μM.2?Cell permeable.
The Uses of Glibenclamide
Glyburide (Glibenclamide) is a sulfonylurea compound that modulates insulin production. Sulfonylureas bind to ATP-dependent K+ channels in beta cells of the pancreas, depolarizing them and stimulating the release of Ca2+, which in turn stimulates insulin production. Glyburide (Glibenclamide) is an ATP-dependent K+ channel (KIR6, KATP) and CFTR Cl- channel blocker. This compound inhibits recombinant CFTR Cl- channels (IC50 = 20 ?M).
What are the applications of Application
Glyburide (Glibenclamide) is an ATP-dependent KIR6 and CFTR Cl- channel blocker
Background
Glyburide is a second generation sulfonylurea used to treat patients with diabetes mellitus type II. It is typically given to patients who cannot be managed with the standard first line therapy, metformin. Glyburide stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations.
Glyburide was granted FDA approval on 1 May 1984. A formulation with metformin was granted FDA approval on on 31 July 2000.
Indications
Glyburide is indicated alone or as part of combination product with metformin, as an adjunct to diet and exercise, to improve glycemic control in adults with type 2 diabetes mellitus.
Pharmacokinetics
Glyburide is a second generation sulfonylurea that stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations. Glibenclamide has a long duration of action as it is given once daily, and a wide therapeutic index as patients are started at doses as low as 0.75mg but that can increase as high as 10mg or more. Patients taking glyburide should be cautioned regarding an increased risk of cardiovascular mortality as seen with tolbutamide, another sulfonylurea.
Metabolism
Glyburide is metabolized mainly by CYP3A4, followed by CYP2C9, CYP2C19, CYP3A7, and CYP3A5. These enzymes metabolize glyburide to 4-trans-hydroxycyclohexyl glyburide (M1), 4-cis-hydroxycyclohexyl glyburide (M2a), 3-cis-hydroxycyclohexyl glyburide (M2b), 3-trans-hydroxycyclohexyl glyburide (M3), 2-trans-hydroxycyclohexyl glyburide (M4), and ethylhydroxycyclohexyl glyburide (M5). The M1 and M2b metabolites are considered active, along with the parent molecule.
Properties of Glibenclamide
Melting point: | 173-175°C |
Density | 1.1805 (rough estimate) |
storage temp. | 2-8°C |
solubility | ethanol: soluble2mg/mL |
form | White solid |
color | White |
Water Solubility | Soluble in ethanol (5 mg/mL), DMSO (25 mg/mL), chloroform (1:36), methanol (1:250), and DMF. Insoluble in water. |
Safety information for Glibenclamide
Signal word | Danger |
Pictogram(s) |
Health Hazard GHS08 |
GHS Hazard Statements |
H370:Specific target organ toxicity, single exposure |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P405:Store locked up. P501:Dispose of contents/container to..… |
Computed Descriptors for Glibenclamide
InChIKey | ZNNLBTZKUZBEKO-UHFFFAOYSA-N |
Abamectin manufacturer
Cadila Pharmaceuticals Ltd
WARUKSHA LABORATORIES PVT LTD
Auro Laboratories Limited
Prudence Pharma Chem
Elixir Pharma
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