Glipizide

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Not to be confused with gliclazide or glyburide.

Glipizide


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^Y
ATC code	A10BB07
PubChem	CID 3478
DrugBank	DB01067
ChemSpider	3359^Y
UNII	X7WDT95N5C^Y
KEGG	D00335^Y
ChEMBL	CHEMBL1073^Y
Chemical data
Formula	C₂₁H₂₇N₅O₄S
Mol. mass	445.536 g/mol
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
Y (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.

External links

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

Oral anti-diabetic drugs and Insulin analogs (A10)

Insulin

Sensitizers

Biguanides	Metformin^# Buformin^‡ Phenformin^‡

TZDs/"glitazones" (PPAR)	Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Secretagogues

K+ ATP

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Metahexamide Tolbutamide Tolazamide 2nd generation: Glibenclamide (Glyburide)^# Glibornuride Glipizide Gliquidone Glisoxepide Glyclopyramide Glimepiride Gliclazide

Meglitinides/"glinides"	Nateglinide Repaglinide Mitiglinide

GLP-1 agonists

DPP-4 inhibitors

GPR40 Free fatty acid receptor 1

Fasiglifam^†

Analogs/other insulins

fast-acting (Insulin lispro
Insulin aspart
Insulin glulisine)
short-acting (Regular insulin)
long-acting (Insulin glargine
Insulin detemir
NPH insulin)
ultra-long-acting (Insulin degludec^†)
inhalable Exubera^‡

Other

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

SGLT2 inhibitors	Canagliflozin Dapagliflozin Empagliflozin^† Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Bromocriptine Benfluorex^‡ Tolrestat^‡

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: END

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noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

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