Glipizide

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Glipizide
Glipizide.svg
Glipizide ball-and-stick.png
Systematic (IUPAC) name
N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
Clinical data
Trade namesGlucotrol
AHFS/Drugs.commonograph
MedlinePlusa684060
Pregnancy cat.
Legal status
  • POM (UK), ℞-only (U.S.)
RoutesOral
Pharmacokinetic data
Bioavailability100% (regular formulation)
90% (extended release)
Protein binding98 to 99%
MetabolismHepatic hydroxylation
Half-life2 to 5 hours
ExcretionRenal and fecal
Identifiers
CAS number29094-61-9 YesY
ATC codeA10BB07
PubChemCID 3478
DrugBankDB01067
ChemSpider3359 YesY
UNIIX7WDT95N5C YesY
KEGGD00335 YesY
ChEBICHEBI:5384 N
ChEMBLCHEMBL1073 YesY
Chemical data
FormulaC21H27N5O4S 
Mol. mass445.536 g/mol
 N (what is this?)  (verify)
 
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Not to be confused with gliclazide or glyburide.
Glipizide
Glipizide.svg
Glipizide ball-and-stick.png
Systematic (IUPAC) name
N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide
Clinical data
Trade namesGlucotrol
AHFS/Drugs.commonograph
MedlinePlusa684060
Pregnancy cat.
Legal status
  • POM (UK), ℞-only (U.S.)
RoutesOral
Pharmacokinetic data
Bioavailability100% (regular formulation)
90% (extended release)
Protein binding98 to 99%
MetabolismHepatic hydroxylation
Half-life2 to 5 hours
ExcretionRenal and fecal
Identifiers
CAS number29094-61-9 YesY
ATC codeA10BB07
PubChemCID 3478
DrugBankDB01067
ChemSpider3359 YesY
UNIIX7WDT95N5C YesY
KEGGD00335 YesY
ChEBICHEBI:5384 N
ChEMBLCHEMBL1073 YesY
Chemical data
FormulaC21H27N5O4S 
Mol. mass445.536 g/mol
 N (what is this?)  (verify)

Glipizide is an oral rapid- and short-acting anti-diabetic drug from the sulfonylurea class. It is classified as a second generation sulfonylurea, which means that it undergoes enterohepatic circulation. Second-generation sulfonylureas are both more potent and have shorter half-lives than the first-generation sulfonylureas.

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.

Mechanism of Action[edit]

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.

Sulfonylureas may also cause the decrease of serum glucagon and potentiate the action of insulin at the extrapancreatic tissues.[citation needed]

Synthesis[edit]

Glipizide synthesis:[1] DE 2012138  U.S. Patent 3,669,966

See also[edit]

References[edit]

  1. ^ Arzneim Forsch. 21,200

External links[edit]