Glipizide

Not to be confused with gliclazide or glyburide.

Glipizide, sold under the brand name Glucotrol among others, is an anti-diabetic medication of the sulfonylurea class used to treat type 2 diabetes.^[1][2] It is used together with a diabetic diet and exercise.^[1][2] It is not indicated for use by itself in type 1 diabetes.^[1][2] It is taken by mouth.^[1][2] Effects generally begin within half an hour and can last for up to a day.^[1]

Glipizide

Clinical data
Trade names	Glucotrol, Glucotrol XL, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684060
License data	US DailyMed: Glipizide
Pregnancy category	AU: C
Routes of administration	By mouth
Drug class	Sulfonylurea
ATC code	A10BB07 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	100% (regular formulation) 90% (extended release)
Protein binding	98 to 99%
Metabolism	Liver hydroxylation
Elimination half-life	2 to 5 hours
Excretion	Kidney and fecal
Identifiers
IUPAC name N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
CAS Number	29094-61-9 Y
PubChem CID	3478
IUPHAR/BPS	6821
DrugBank	DB01067 Y
ChemSpider	3359 Y
UNII	X7WDT95N5C
KEGG	D00335 Y
ChEBI	CHEBI:5384 N
ChEMBL	ChEMBL1073 Y
CompTox Dashboard (EPA)	DTXSID0040676
ECHA InfoCard	100.044.919
Chemical and physical data
Formula	C21H27N5O4S
Molar mass	445.54 g·mol−1
3D model (JSmol)	Interactive image
Melting point	208 to 209 °C (406 to 408 °F)
SMILES O=C(c1ncc(nc1)C)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3
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
NY (what is this?)  (verify)

Common side effects include nausea, diarrhea, low blood sugar, and headache.^[1] Other side effects include sleepiness, skin rash, and shakiness.^[3] The dose may need to be adjusted in those with liver or kidney disease.^[1] Use during pregnancy or breastfeeding is not recommended.^[3] It works by stimulating the pancreas to release insulin and increases tissue sensitivity to insulin.^[1]

Glipizide was approved for medical use in the United States in 1984.^[1] It is available as a generic medication.^[1] In 2022, it was the 42nd most commonly prescribed medication in the United States, with more than 14 million prescriptions.^[4][5]

Mechanism of action

Glipizide sensitizes the beta cells of pancreatic islets of Langerhans insulin response, meaning that more insulin is released in response to glucose than would be without glipizide ingestion.^[2] Glipizide acts by partially blocking potassium channels among beta cells of pancreatic islets of Langerhans. By blocking potassium channels, the cell depolarizes, which results in the opening of voltage-gated calcium channels. The resulting calcium influx encourages insulin release from beta cells.^[6]

History

It was patented in 1969, and approved for medical use in 1971.^[7] Glipizide was approved for medical use in the United States in 1984.^[1]