Glipizide

Glipizide
Clinical data
Trade names	Glucotrol
AHFS/Drugs.com	Monograph
MedlinePlus	a684060
Pregnancy; category	AU: C; ;
Routes of; administration	Oral
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	Hepatic hydroxylation
Elimination half-life	2 to 5 hours
Excretion	Renal and fecal
Identifiers
	IUPAC name N-(4-[N-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-5-methylpyrazine-2-carboxamide;
CAS Number	29094-61-9 ;
PubChem CID	3478;
IUPHAR/BPS	6821;
DrugBank	DB01067 ;
ChemSpider	3359 ;
UNII	X7WDT95N5C;
KEGG	D00335 ;
ChEBI	CHEBI:5384 ;
ChEMBL	ChEMBL1073 ;
CompTox Dashboard (EPA)	DTXSID0040676 ;
ECHA InfoCard	100.044.919
Chemical and physical data
Formula	C21H27N5O4S
Molar mass	445.536 g/mol 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) ; Key:ZJJXGWJIGJFDTL-UHFFFAOYSA-N ;
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Glipizide is an oral rapid- and short-acting anti-diabetic medication 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

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^[1]. 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. ^[2]

References

^ Drugs@FDA (the official database of FDA-approved drugs) https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020329s025lbl.pdf
^ LH Bösenberg & DG van Zyl (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, 80-88, DOI: 10.1080/22201009.2008.1087217

External links

Glucotrol XL Full U.S. Prescribing Information. Accessed on July 26, 2005.

[1] Drugs@FDA (the official database of FDA-approved drugs) https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020329s025lbl.pdf

[2] LH Bösenberg & DG van Zyl (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, 80-88, DOI: 10.1080/22201009.2008.1087217

[1]

[2]

Mechanism of action

See also

References

External links