Glipizide

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 namesGlucotrol, Glucotrol XL, others
AHFS/Drugs.comMonograph
MedlinePlusa684060
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth
Drug classSulfonylurea
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% (regular formulation)
90% (extended release)
Protein binding98 to 99%
MetabolismLiver hydroxylation
Elimination half-life2 to 5 hours
ExcretionKidney and fecal
Identifiers
IUPAC name
  • N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.044.919
Chemical and physical data
FormulaC21H27N5O4S
Molar mass445.54 g·mol−1
3D model (JSmol)
Melting point208 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 2020, it was the 49th most commonly prescribed medication in the United States, with more than 13 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]

References

  1. "Glipizide Monograph for Professionals". Drugs.com. AHFS. Retrieved 24 December 2018.
  2. "Glucotrol XL- glipizide tablet, extended release". DailyMed. 17 August 2018. Retrieved 31 July 2020.
  3. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 693. ISBN 9780857113382.
  4. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  5. "Glipizide - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  6. Bösenberg LH, Van Zyl DG (December 2008). "The mechanism of action of oral antidiabetic drugs: a review of recent literature". Journal of Endocrinology, Metabolism and Diabetes of South Africa. 13 (3): 80–8. doi:10.1080/22201009.2008.10872177.
  7. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 449. ISBN 9783527607495.
  • "Glipizide". Drug Information Portal. U.S. National Library of Medicine.
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