Glipizide

Base Information

• Chemical Name: Glipizide
• CAS No.: 29094-61-9
• Deprecated CAS: 172964-66-8,29094-66-4,38777-27-4
• Molecular Formula: C21H27N5O4S
• Molecular Weight: 445.542
• Hs Code.: 29350090
• European Community (EC) Number: 249-427-6
• NSC Number: 759120
• UNII: X7WDT95N5C
• DSSTox Substance ID: DTXSID0040676
• Nikkaji Number: J20.336J
• Wikipedia: Glipizide
• Wikidata: Q3108899
• NCI Thesaurus Code: C29074
• RXCUI: 4821
• Pharos Ligand ID: UZJ1JGLTGNPZ
• Metabolomics Workbench ID: 43304
• ChEMBL ID: CHEMBL1073
• Mol file: 29094-61-9.mol

Synonyms:Glidiazinamide;Glipizide;Glucotrol;Glupitel;Glydiazinamide;Glypidizine;K 4024;K-4024;K4024;Melizide;Mindiab;Minidiab;Minodiab;Ozidia

Chemical Property of Glipizide

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 208-209 °C
• Refractive Index: 1.597
• PKA: pKa 5.9 (Uncertain)
• PSA: 138.53000
• Density: 1.34 g/cm³
• LogP: 4.33160
• Storage Temp.: -20°C Freezer
• Solubility.: methanol: 1.9 mg/mL
• Water Solubility.: methanol: 1.9 mg/mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 445.17837553
• Heavy Atom Count: 31
• Complexity: 697

Purity/Quality:

98%-102% , ^*data from raw suppliers

Glipizide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 24/25-53-36/37-26-25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C=N1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
• Recent ClinicalTrials: Comparison of Type 2 Diabetes Pharmacotherapy Regimens
• Recent EU Clinical Trials: A Randomised Controlled Trial for People with Established Type 2 Diabetes during Ramadan: Canagliflozin (Invokana?) vs. standard dual therapy regimen: The ‘Can Do Ramadan’ Study
• 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.
• Uses: sweetener, treatment of portoencephalopathy 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. A hypoglycemic agent that enhances insulin secretion.
• Therapeutic Function: Oral hypoglycemic
• 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 by coumarins; also possibly changes to INR. Antifungals: concentration increased by fluconazole, posaconazole and miconazole and possibly voriconazole - avoid with miconazole. Ciclosporin: may increase ciclosporin levels. Lipid-regulating drugs: possibly additive hypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas.

Technology Process of Glipizide

There total 11 articles about Glipizide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

cyclohexylcarbamic acid phenyl ester (56379-88-5) + N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide (33288-71-0) → glipizide (29094-61-9,29094-66-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 80 ℃; for 0.0833333h; under 3750.38 Torr; Temperature;

DOI:10.1002/chem.202103196

Reference yield: 85.0%

carbon monoxide (201230-82-2) + C14H16N4O3S*NaCl + cyclohexylamine (108-91-8,157973-60-9) → glipizide (29094-61-9,29094-66-4)

Guidance literature:

With iron(III)-acetylacetonate; In methanol; at 20 - 30 ℃; for 6h;

Reference yield: 84.0%

N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea (2015-16-9) + 5-methylpyrazine-2-carboxylic acid methyl ester (41110-33-2) → glipizide (29094-61-9,29094-66-4)

Guidance literature:

With water; sodium methylate; In methanol; at 85 ℃; Concentration; Temperature; Solvent;

upstream raw materials:

1-ethenyl-2-pyrrolidinone

carbon monoxide

cyclohexylamine

N-(4-[2-amino-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea

Downstream raw materials:

N-[2-[4-(amino-sulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide

C₂₁H₂₇N₅O₄S*C₄₂H₇₀O₃₅

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF GLIPIZIDE". Page/Page column 20; 21; 22. . Retrieved 2018/05/24.
• 2、 -. "OSMOTIC PUMP CONTROLLED RELEASE TABLET AND PREPARATION METHOD THEREOF". . . Retrieved 2012/07/30.