Glibenclamide

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Glibenclamide
Systematic (IUPAC) name
5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl) phenyl]ethyl]-2-methoxy-benzamide
Identifiers
CAS number	10238-21-8
ATC code	A10BB01
PubChem	3488
DrugBank	APRD00233
Chemical data
Formula	C23H28ClN3O5S
Mol. mass	494.004 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	Extensive
Metabolism	Hepatic hydroxylation (CYP2C9-mediated)
Half life	10 hours
Excretion	Renal and biliary
Therapeutic considerations
Licence data	US
Pregnancy cat.	C(AU) B(US)
Legal status	POM(UK) ℞-only(US)
Routes	Oral

Glibenclamide (INN), also known as glyburide (USAN), is an anti-diabetic drug in a class of medications known as sulfonylureas, used in the treatment of type II diabetes. As of 2007, it is one of only two oral anti-diabetics in the World Health Organization Model List of Essential Medicines (the other being metformin).^[1]

It is sold in doses of 1.25 mg, 2.5 mg and 5 mg, under the trade names Diabeta, Glynase and Micronase in the United States and Daonil, Semi-Daonil and Euglucon in the United Kingdom.

It is also sold in combination with metformin under the trade name Glucovance.

Additionally, recent research shows that glyburide improves outcome in animal stroke models by preventing brain swelling. A retrospective study showed that in type 2 diabetic patients already taking glyburide there was improved NIH stroke scale scores on discharge compared to diabetic patients not taking glyburide.

[edit] Mechanism of action

The drug works by inhibiting ATP-sensitive potassium channels in pancreatic beta cells. This inhibition causes cell membrane depolarization, opening of voltage-dependent calcium channels, thus triggering an increase in intracellular calcium into the beta cell which stimulates insulin release.

[edit] Side effects and contraindications

The drug is contraindicated in pregnant women. It is also a major cause of drug induced hypoglycemia.Cholestatic jaundice is noted.

Recently published data suggests that glibenclamide is associated with significantly higher annual mortality when combined with metformin than other insulin-secreting medications, after correcting for other potentially confounding patient characteristics. The safety of this combination has been questioned.^[2]

[edit] References

v • d • e Oral antidiabetic drugs and Insulin analogs (A10) Biguanides Metformin Sulfonylureas Carbutamide, Chlorpropamide, Glibenclamide (Glyburide), Gliclazide, Glimepiride, Glipizide, Gliquidone, Tolazamide, Tolbutamide Alpha-glucosidase inhibitors Acarbose, Miglitol, Voglibose Thiazolidinediones (TZD) Pioglitazone, Rivoglitazone†, Rosiglitazone, Troglitazone‡ Meglitinides Nateglinide, Repaglinide, Mitiglinide Dipeptidyl peptidase-4 (DPP-4) inhibitors Alogliptin†, Saxagliptin†, Sitagliptin, Vildagliptin Glucagon-like peptide-1 analog Exenatide, Liraglutide†, Albiglutide† Amylin analog Pramlintide Insulin analogs fast acting (Insulin lispro, Insulin aspart, Insulin glulisine), long acting (Insulin glargine, Insulin detemir), Inhalable insulin (Exubera) Dual PPAR agonists Aleglitazar†, Muraglitazar§, Tesaglitazar§ SGLT2 inhibitor Dapagliflozin†, Remogliflozin† †Undergoing clinical trials. ‡ Withdrawn from market. §Development halted.