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
Glipizide.svg
Glipizide ball-and-stick.png
Clinical data
Trade namesGlucotrol, Glucotrol XL, others
AHFS/Drugs.comMonograph
MedlinePlusa684060
Pregnancy
category
  • AU: C
Routes of
administration		By mouth
Drug classSulfonylurea
ATC code
  • A10BB07 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
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
  • 29094-61-9 check
PubChem CID
  • 3478
IUPHAR/BPS
  • 6821
DrugBank
  • DB01067 check
ChemSpider
  • 3359 check
UNII
  • X7WDT95N5C
KEGG
  • D00335 check
ChEBI
  • CHEBI:5384 ☒
ChEMBL
  • ChEMBL1073 check
CompTox Dashboard (EPA)
  • DTXSID0040676 Edit this at Wikidata
ECHA InfoCard100.044.919 Edit this at Wikidata
Chemical and physical data
FormulaC21H27N5O4S
Molar mass445.54 g·mol−1
3D model (JSmol)
  • Interactive image
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) check
  • Key:ZJJXGWJIGJFDTL-UHFFFAOYSA-N check
 ☒check (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 2018, it was the 44th most commonly prescribed medication in the United States, with more than 17 million prescriptions.[4][5]

Mechanism of actionEdit

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]

HistoryEdit

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]

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.