Glipizide

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Glipizide chemical structure
Glipizide
Systematic (IUPAC) name
N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]- 5-methyl-pyridine-2-carboxamide
Identifiers
CAS number 29094-61-9
ATC code A10BB07
PubChem 3478
DrugBank APRD00436
Chemical data
Formula C21H27N5O4S 
Mol. weight 445.536 g/mol
Pharmacokinetic data
Bioavailability 100% (regular formulation)
90% (extended release)
Protein binding 98 to 99%
Metabolism Hepatic hydroxylation
Half life 2 to 5 hours
Excretion Renal and fecal
Therapeutic considerations
Pregnancy cat.

C (Au, U.S.)

Legal status

POM (UK), ℞-only (U.S.)

Routes Oral

Glipizide is an oral medium-to-long acting anti-diabetic drug from the sulfonylurea class. It is classified as a second generation Sulfonylurea, which means that it undergoes enterohepatic circulation. The structure on the R2 group is a much larger cyclo or aromatic group compared to the 1st generation sulfonylureas. This leads to a once a day dosing that is much less than the first generation, about 100 fold.

Mechanism of action is produced by blocking potassium K+ channels in the Beta cells of the Islets of Langerhans. By partially blocking the K+ channels, you will increase the time the cell spends in the Calcium release stage of cell signaling leading to an increase in calcium. The increase in Calcium will initiate more Insulin release from each Beta cell.

It is available under the brand name Glucotrol® by Pfizer, originally available in 1984. Pfizer sells Glucotrol in doses of 5 and 10 milligrams and Glucotrol XL (an extended release form of glipizide) in doses of 2.5, 5, and 10 milligrams. Other companies sell generic forms of glipizide, most commonly extended release tablets of 5 and 10 milligrams.

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Oral antidiabetic drugs (A10B) edit
Biguanides: Metformin
Sulfonylureas: Chlorpropamide, glibenclamide (Glyburide), Gliclazide, Glimepiride, Glipizide, Gliquidone, Tolazamide, Tolbutamide
Alpha-glucosidase inhibitor: Acarbose, Miglitol
Thiazolidinediones (TZD): Pioglitazone, Rosiglitazone, Troglitazone
Meglitinides: Nateglinide, Repaglinide, Mitiglinide
Dipeptidyl peptidase-4 (DPP-4) inhibitors: Saxagliptin, Sitagliptin, Vildagliptin