Glipizide

Title: Glipizide
CAS Registry Number: 29094-61-9
CAS Name: N-[2-[4-[[[(Cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methylpyrazinecarboxamide
Additional Names: 1-cyclohexyl-3-[[p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea; glydiazinamide
Manufacturers' Codes: K-4024
Trademarks: Glibenese (Pfizer); Glucotrol (Pfizer); Mindiab (Pfizer); Minidiab (Pfizer); Ozidia (Pfizer)
Molecular Formula: C21H27N5O4S
Molecular Weight: 445.54
Percent Composition: C 56.61%, H 6.11%, N 15.72%, O 14.36%, S 7.20%
Literature References: Second generation sulfonylurea with hypoglycemic activity. Prepn: V. Ambrogi, W. Logemann, DE 2012138; eidem, US 3669966 (1970, 1972 both to Carlo Erba); Ambrogi et al., Arzneim.-Forsch. 21, 200 (1971). Pharmacology: eidem, ibid. 208; Marigo et al., ibid. 215. Metabolism: Goldaniga et al., ibid. 23, 242 (1973); Fuccella et al., J. Clin. Pharmacol. 13, 68 (1973). Toxicity: Ambrogi et al., Arzneim.-Forsch. 21, 208 (1971). Review of pharmacology and therapeutic efficacy: R. N. Brogden et al., Drugs 18, 329-353 (1979); H. E. Lebovitz, Pharmacotherapy 5, 63-77 (1985).
Properties: Crystals from ethanol, mp 208-209°. Also reported as mp 200-203°. LD50 in mice, rats (g/kg): >3, 1.2 i.p. (Ambrogi).
Melting point: mp 208-209°; mp 200-203°
Toxicity data: LD50 in mice, rats (g/kg): >3, 1.2 i.p. (Ambrogi)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic; Sulfonylurea Derivatives.
Gliquidone Glisoxepid Globin Glucagon Glucagon-Like Peptides

Glipizide
Glipizide.svg
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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 YesY
ATC code A10BB07
PubChem CID 3478
DrugBank DB01067
ChemSpider 3359 YesY
UNII X7WDT95N5C YesY
KEGG D00335 YesY
ChEBI CHEBI:5384 N
ChEMBL CHEMBL1073 YesY
Chemical data
Formula C21H27N5O4S 
Mol. mass 445.536 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.

Glucotrol XL 5 MG Extended Release 24 hour tablet

Mechanism of action is produced by blocking potassium channels in the beta cells of the islets of Langerhans. By partially blocking the potassium channels, the cell remains depolarized, increasing the time the cell spends in the calcium release stage, which results in signaling leading to calcium influx. The increase in calcium will initiate more insulin release from each beta cell. Sulfonylureas may also cause the decrease of serum glucagon and potentiate the action of insulin at the extrapancreatic tissues.

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.