Glipizide CAS 29094-61-9
Introduction：Basic information about Glipizide CAS 29094-61-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Glipizide Basic informationDescription References
| Product Name: | Glipizide |
| Synonyms: | N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-2-pyrazinecarboxamide;Glipizide Solution, 100ppm;Melizide;n-(4-(beta-(5-methylpyrazine-2-carboxamido)ethyl)benzenesulphonyl)-n’-cycloh;tk1320;urea,1-cyclohexyl-3-((p-(2-(5-methylpyrazinecarboxamido)ethyl)phenyl)sulfonyl);GLYDIAZINAMIDE;GLIPIZIDE |
| CAS: | 29094-61-9 |
| MF: | C21H27N5O4S |
| MW: | 445.54 |
| EINECS: | 249-427-6 |
| Product Categories: | Diabetes Research;Sulfur & Selenium Compounds;API;Amines;Heterocycles;Potassium channel;Intermediates & Fine Chemicals;Pharmaceuticals;API's;29094-61-9 |
| Mol File: | 29094-61-9.mol |
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 |
| pka | pKa 5.9 (Uncertain) |
| form | solid |
| color | white |
| Merck | 14,4442 |
| BCS Class | 2 (CLogP), 4 (LogP) |
| Major Application | pharmaceutical (small molecule) |
| InChIKey | ZJJXGWJIGJFDTL-UHFFFAOYSA-N |
| SMILES | S(C1C=CC(=CC=1)CCNC(C1=NC=C(N=C1)C)=O)(=O)(=O)NC(=O)NC1CCCCC1 |
| CAS DataBase Reference | 29094-61-9(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Pyrazinecarboxamide, N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl- (29094-61-9) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 21-36/38-46-62-63 |
| Safety Statements | 24/25-53-36/37-26-25 |
| WGK Germany | 3 |
| RTECS | YS7640000 |
| F | 10 |
| HS Code | 29350090 |
| Storage Class | 11 - Combustible Solids |
| Toxicity | LD50 in mice, rats (g/kg): >3, 1.2 i.p. (Ambrogi) |
| Description | Glipizide 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. |
| References | https://en.wikipedia.org/wiki/Glipizide http://www.medicinenet.com/glipizide/article.htm http://www.medicinenet.com/glipizide_tablet-oral/article.htm https://www.drugbank.ca/drugs/DB01067 |
| Chemical Properties | Crystalline Solid |
| Originator | Minidiab,Carlo Erba,Italy,1973 |
| Uses | sweetener, treatment of portoencephalopathy |
| Uses | Labelled 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. |
| Uses | A hypoglycemic agent that enhances insulin secretion. |
| Definition | ChEBI: 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 Process | 5-Methyl pyrazine-2-carboxylic acid is refluxed with thionyl chloride inanhydrous benzene for approximately 12 hours. Benzene and thionyl chlorideexcess is removed by distillation. Then some anhydrous dioxane is added andthis acid chloride solution is allowed to drop into p-(β-aminoethyl)-benzenesulfonamide suspension in dioxane and anhydrous pyridine. Theresulting mixture is then refluxed for 3 hours. Dioxane is removed bydistillation and then the residue is washed with water and acetic acid. The rawacylated sulfonamide is then filtered and crystallized from 95% ethanol, thusobtaining a product of MP 200° to 203°C. This product is then reacted with cyclohexyl isocyanate to give glipizide. |
| Brand name | Glucotrol (Pfizer). |
| Therapeutic Function | Oral hypoglycemic |
| General Description | Glipizide 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 Description | Glipizide, 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 Description | Structurally, 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. |
| Biochem/physiol Actions | Potassium inwardly-rectifying channel, subfamily J, member 1 (KCNJ1) plays a vital role in potassium balance. It is an ATP-dependent K+?channel blocker. The encoded protein is liable for the elimination of potassium in exchange for the absorption of sodium by the epithelial sodium channel (ENaC). Mutation in KCNJ1 is linked with several diseases, such as, antenatal Bartter syndrome and diabetes. Glipizide helps to repress the development of tumors and metastasis by preventing angiogenesis. |
| Clinical Use | Non-insulin dependent diabetes mellitus |
| Synthesis | Glipizide, 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 themolecule, in which the 2-methoxy-5-chlorobenzoic acid part is replaced with 6-methylpyrazincarboxylic acid. It is also synthesized by a synthesis alternative to thosedescribed above. In the given scheme, 6-methylpyrazincarboxylic acid is initially reactedwith thionyl chloride, resulting in the corresponding chloride, which undergoes furtheraction with 4-(2-aminoethyl)benzenesulfonamide, forming the corresponding amide26.2.12. The resulting sulfonamide is reacted in a traditional scheme with cyclohexylisocyanate,forming the desired glipizide (26.2.13). |
| Veterinary Drugs and Treatments | Glipizide may be of benefit in treating cats with type II diabetes ifthey have a population of functioning beta cells. It has been suggestedthat there are two situations when glipizide can be recommended,1) If an owner refuses to consider using insulin usuallydue to a fear of needles, and 2) the cat appears to be relatively wellcontrolled on quite small doses of insulin and the owner wouldstrongly prefer to no longer give insulin (Feldman 2005b). While glipizide potentially could be useful in treating canine patientswith type II or III diabetes, however, by the time dogs presentwith hyperglycemia, they are absolutely or relatively insulinopenicand glipizide would unlikely be effective. |
| Drug interactions | Potentially hazardous interactions with other drugs Analgesics: effects enhanced by NSAIDs. Antibacterials: effects enhanced by chloramphenicol,sulphonamides, tetracyclines and trimethoprim;effect reduced by rifamycins. Anticoagulants: effect possibly enhanced bycoumarins; also possibly changes to INR. Antifungals: concentration increased by fluconazole,posaconazole and miconazole and possiblyvoriconazole - avoid with miconazole. Ciclosporin: may increase ciclosporin levels. Lipid-regulating drugs: possibly additivehypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas. |
| Metabolism | The metabolism of glipizide is extensive and occursmainly in the liver. The primary metabolites are inactivehydroxylation products and polar conjugates and areexcreted mainly in the urine. |
| References | [1] Patent: WO2018/78657, 2018, A1. Location in patent: Page/Page column 20; 21; 22 |
Glipizide Preparation Products And Raw materials
| Raw materials | 2-PhenylethylaMine-->Thionyl chloride-->Des(5-Methylpyrazinecarbonyl) Glipizide-->METHYL 5-METHYLPYRAZINE-2-CARBOXYLATE-->Sodium Methoxide-->Water-->Methanol |
