Glipizide

Not to be confused with gliclazide or glyburide.

Glipizide

Systematic (IUPAC) name
N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
Clinical data
Trade names	Glucotrol
AHFS/Drugs.com	monograph
MedlinePlus	a684060
Pregnancy cat.	C (Au, U.S.)
Legal status	POM (UK), ℞-only (U.S.)
Routes	Oral
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
Identifiers
CAS number	29094-61-9
ATC code	A10BB07
PubChem	CID 3478
DrugBank	DB01067
ChemSpider	3359^Y
UNII	X7WDT95N5C^Y
KEGG	D00335^Y
ChEMBL	CHEMBL1073^Y
Chemical data
Formula	C₂₁H₂₇N₅O₄S
Mol. mass	445.536 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)^Y Key:ZJJXGWJIGJFDTL-UHFFFAOYSA-N^Y
Y(what is this?) (verify)

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 channels in the beta cells of the islets of Langerhans. By partially blocking the potassium channels, it 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.

Originally available in 1984, it is marketed by Pfizer under the brand name Glucotrol in the USA, where 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 also market glipizide, most commonly extended release tablets of 5 and 10 milligrams.

External links

Glucotrol XL Full U.S. Prescribing Information. Accessed on July 26, 2005.

Oral anti-diabetic drugs and Insulin analogs (A10)

Insulin

Sensitizers

Biguanides	Metformin^# • Buformin^‡ • Phenformin^‡

TZDs (PPAR)	Pioglitazone • Rivoglitazone^† • Rosiglitazone • Troglitazone^‡

Dual PPAR agonist	Aleglitazar^† • Muraglitazar^§ • Tesaglitazar^§

Secretagogues

K+ ATP

Sulfonylureas	1st generation: Acetohexamide • Carbutamide • Chlorpropamide • Tolbutamide • Tolazamide 2nd generation: Glibenclamide (Glyburide)^# • Glipizide • Gliquidone • Glyclopyramide • Glimepiride • Gliclazide •

Meglitinides/"glinides"	Nateglinide • Repaglinide • Mitiglinide

GLP-1 analogs

Exenatide • Liraglutide • Taspoglutide^† • Albiglutide^† • Lixisenatide

DPP-4 inhibitors

Alogliptin^† • Linagliptin • Saxagliptin • Sitagliptin • Vildagliptin

Analogs/other insulins

fast-acting (Insulin lispro • Insulin aspart • Insulin glulisine) • short-acting (Regular insulin) • long-acting (Insulin glargine • Insulin detemir • NPH insulin) • ultra-long-acting (Insulin degludec^†) • inhalable Exubera^‡

Other

Alpha-glucosidase inhibitors	Acarbose • Miglitol • Voglibose

Amylin analog	Pramlintide

SGLT2 inhibitors	Canagliflozin^† • Dapagliflozin^† • Remogliflozin^§ • Sergliflozin^§

Other	Benfluorex^‡ • Tolrestat^‡

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

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proc, drug (A10/H1/H2/H3/H5)