Glyburide

Glibenclamide

Clinical data
Trade names	see below
AHFS/Drugs.com	International Drug Names
MedlinePlus	a684058
License data	US FDA: Glyburide
Pregnancy category	AU: C US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	A10BB01 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Protein binding	Extensive
Metabolism	Hepatic hydroxylation (CYP2C9-mediated)
Biological half-life	10 hours
Excretion	Renal and biliary
Identifiers
IUPAC name 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl) phenyl]ethyl]-2-methoxybenzamide
CAS Number	10238-21-8 Y
PubChem (CID)	3488
IUPHAR/BPS	2414
DrugBank	DB01016 Y
ChemSpider	3368 Y
UNII	SX6K58TVWC Y
KEGG	D00336 Y
ChEBI	CHEBI:5441 Y
ChEMBL	CHEMBL472 Y
ECHA InfoCard	100.030.505
Chemical and physical data
Formula	C23H28ClN3O5S
Molar mass	494.004 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCNC(=O)c3cc(Cl)ccc3OC
InChI 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) Y Key:ZNNLBTZKUZBEKO-UHFFFAOYSA-N Y

Glibenclamide (AAN, BAN, INN), also known as glyburide (USAN), is an antidiabetic drug in a class of medications known as sulfonylureas, closely related to sulfonamide antibiotics. It was developed in 1966 in a cooperative study between Boehringer Mannheim (now part of Roche) and Hoechst (now part of Sanofi-Aventis).

It is used in the treatment of type 2 diabetes. As of 2003, in the United States, it was the most popular sulfonylurea.

It is not as good as either metformin or insulin in those who have gestational diabetes.

This drug is a major cause of drug-induced hypoglycemia. The risk is greater than with other sulfonylureas. Cholestatic jaundice is noted.

Glibenclamide may be not recommended in those with G6PD deficiency, as it may cause acute haemolysis.

Recently published data suggest 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.

The drug works by binding to and inhibiting the ATP-sensitive potassium channels (K_ATP) inhibitory regulatory subunit sulfonylurea receptor 1 (SUR1) in pancreatic beta cells. This inhibition causes cell membrane depolarization, opening voltage-dependent calcium channels. This results in an increase in intracellular calcium in the beta cell and subsequent stimulation of insulin release.