ChemicalBook > Product Catalog > API > Hormones and the Endocrine System > Pancreatic hormone and blood sugar regulation > Glipizide
Glipizide Chemical Properties
- Melting point:208-209°C
- Density 1.34±0.1 g/cm3(Predicted)
- storage temp. 2-8°C
- solubility methanol: 1.9 mg/mL
- form solid
- pkapKa 5.9 (Uncertain)
- color white
- Merck 14,4442
- CAS DataBase Reference29094-61-9(CAS DataBase Reference)
- EPA Substance Registry System2-Pyrazinecarboxamide, N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl- (29094-61-9)
Glipizide Usage And Synthesis
- DescriptionGlipizide is an oral rapid- and short-acting anti-diabetic medication classified as a second-generation sulfonylurea. It is commonly used as an adjunct to diet in combination with proper exercise program for controlling high blood sugar and its associated symptomatology in people with type II diabetes (non-insulin-dependent diabetes mellitus). Besides, it is effective to lessen the risk of heart attack or stroke and help prevent kidney damage, blindness, nerve problems, loss of limbs, sexual function problems, which can be resulted from hypertension.
Glipizide is an oral hypoglycemic drug that is rapidly absorbed and completely metabolized in human body. It is occasionally be administrated with other diabetes pharmaceuticals but it is not a cure for diabetes. Glipizide lowers blood glucose by stimulating the pancreas to release more natural insulin. The FDA approved glipizide in May 1984.
- Chemical PropertiesCrystalline Solid
- OriginatorMinidiab,Carlo Erba,Italy,1973
- Usessweetener, treatment of portoencephalopathy
- UsesLabelled Glipizide . A sulfonylurea hypoglycemic agent. Used as an antidiabetic.;Labeled Glipizide, intended for use as an internal standard for the quantification of Glipizide by GC- or LC-mass spectrometry.
- UsesA hypoglycemic agent that enhances insulin secretion.
- DefinitionChEBI: An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.
- Manufacturing Process5-Methyl pyrazine-2-carboxylic acid is refluxed with thionyl chloride in
anhydrous benzene for approximately 12 hours. Benzene and thionyl chloride
excess is removed by distillation. Then some anhydrous dioxane is added and
this acid chloride solution is allowed to drop into p-(β-aminoethyl)-
benzenesulfonamide suspension in dioxane and anhydrous pyridine. The
resulting mixture is then refluxed for 3 hours. Dioxane is removed by
distillation and then the residue is washed with water and acetic acid. The raw
acylated sulfonamide is then filtered and crystallized from 95% ethanol, thus
obtaining a product of MP 200° to 203°C.
This product is then reacted with cyclohexyl isocyanate to give glipizide.
- brand nameGlucotrol (Pfizer).
- Therapeutic FunctionOral hypoglycemic
- General DescriptionGlipizide is N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-2-pyrazinecarboxamide;this compound can also be named as the urea—seepreceding discussion (Glucotrol, generic). In the UnitedStates, combinations are available with metformin (Metaglip,generic; tablets, mg glipizide/mg metformin as hydrochloride:2.5/250, 2.5/500, 5/500). Extended-release tablets are available(Glucotrol XL, generic). The pyrazine moiety within thisstructure renders the molecule significantly more hydrophilicthan the similar molecule glyburide, albeit also moderatelyless potent on a dosage as well as target-level basis.
- General DescriptionGlipizide, 1-cyclohexyl-3-[[p-(2-(5-methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea(Glucotrol), is an off-white, odorless powder with a pKa of5.9. It is insoluble in water and alcohols, but soluble in 0.1 NNaOH. Even though on a weight basis, it is approximately100 times more potent than tolbutamide, the maximal hypoglycemiceffects of these two agents are similar. It is rapidlyabsorbed on oral administration, with a serum half-life of 2 to4 hours, whereas the hypoglycemic effects range from 12 to24 hours. Metabolism of glipizide is generally through oxidationof the cyclohexane ring to the p-hydroxy and m-hydroxymetabolites. A minor metabolite that occurs involves theN-acetyl derivative, which results from the acetylation of theprimary amine following hydrolysis of the amide system byamidase enzymes.
- General DescriptionStructurally, glipizide, 1-cyclohexyl-3-[[p-[2(methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea(Glucotrol), is a cyclohexylsulfonylurea analog similar toacetohexamide and glyburide. The drug is absorbed rapidlyon oral administration. Its serum half-life is 2 to 4 hours, andit has a hypoglycemic effect that ranges from 12 to 24 hours.
- Chemical SynthesisGlipizide, 1-cyclohexyl-3-[[p-[2-(5-methylpyrazincarboxamido)ethyl]phenyl]
sulfonyl]urea (26.2.13), differs from glyburide in the structure of the amide region of the
molecule, in which the 2-methoxy-5-chlorobenzoic acid part is replaced with 6-
methylpyrazincarboxylic acid. It is also synthesized by a synthesis alternative to those
described above. In the given scheme, 6-methylpyrazincarboxylic acid is initially reacted
with thionyl chloride, resulting in the corresponding chloride, which undergoes further
action with 4-(2-aminoethyl)benzenesulfonamide, forming the corresponding amide
26.2.12. The resulting sulfonamide is reacted in a traditional scheme with cyclohexylisocyanate,
forming the desired glipizide (26.2.13).
- Veterinary Drugs and TreatmentsGlipizide may be of benefit in treating cats with type II diabetes if
they have a population of functioning beta cells. It has been suggested
that there are two situations when glipizide can be recommended,
1) If an owner refuses to consider using insulin usually
due to a fear of needles, and 2) the cat appears to be relatively well
controlled on quite small doses of insulin and the owner would
strongly prefer to no longer give insulin (Feldman 2005b).
While glipizide potentially could be useful in treating canine patients with type II or III diabetes, however, by the time dogs present with hyperglycemia, they are absolutely or relatively insulinopenic and glipizide would unlikely be effective.
Glipizide Preparation Products And Raw materials
- Raw materialsPhenethylamine
- Pyrazine Glimepiride Glibenclamide N-(aminocarbonyl)benzenesulphonamide N-CYCLOHEXYLFORMAMIDE METHYL-PYRAZIN-2-YLMETHYL-AMINE glycyclamide 4-(2-aminoethyl)benzenesulfonamide (intermediate of glibenclamide,glipizide,gliquidone) 5-methylpyrazine-2-carbaldehyde 4-Ethylbenzenesulfonamide CYCLOHEXANE-D11 Cyclohexylurea 5-METHYL-PYRAZINE-2-CARBOXAMIDE 2,5-Dimethyl pyrazine Glipizide CYCLOHEXYLDIETHANOLAMINE Methanesulfonamide Ethanesulfonyl chloride
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