Glyburide

Base Information

• Chemical Name: Glyburide
• CAS No.: 10238-21-8
• Molecular Formula: C23H28 Cl N3 O5 S
• Molecular Weight: 494.011
• Hs Code.: 29350090
• European Community (EC) Number: 233-570-6
• NSC Number: 759618
• UNII: SX6K58TVWC
• DSSTox Substance ID: DTXSID0037237
• Nikkaji Number: J3.430D
• Wikipedia: Glibenclamide
• Wikidata: Q420626
• NCI Thesaurus Code: C29076
• RXCUI: 4815
• Pharos Ligand ID: AAS44NBKFTWL
• Metabolomics Workbench ID: 43261
• ChEMBL ID: CHEMBL472
• Mol file: 10238-21-8.mol

Synonyms:Daonil;Diabeta;Euglucon 5;Euglucon N;Glibenclamide;Glybenclamide;Glyburide;HB 419;HB 420;HB-419;HB-420;HB419;HB420;Maninil;Micronase;Neogluconin

Chemical Property of Glyburide

Chemical Property:

• Appearance/Colour: white or almost white crystalline podwer
• Melting Point: 173-175 °C
• Refractive Index: 1.628
• PKA: 5.3(at 25℃)
• PSA: 121.98000
• Density: 1.36 g/cm³
• LogP: 5.89520
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble2mg/mL
• Water Solubility.: Soluble in ethanol (5 mg/mL), DMSO (25 mg/mL), chloroform (1:36), methanol (1:250), and DMF. Insoluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 493.1438199
• Heavy Atom Count: 33
• Complexity: 746

Purity/Quality:

99.5% ^*data from raw suppliers

Glyburide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36/37/39-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
• Recent ClinicalTrials: Glycaemic & Cardiovascular Treatment Outcomes of Voglibose Vs Glibenclamide Added to Metformin in T2DM Patients
• Recent EU Clinical Trials: A Multicenter, Double-Blind, Multidose, Placebo-Controlled, Randomized, Parallel-Group, Phase 2 Study to Evaluate the Efficacy and Safety of Intravenous BIIB093 for Patients with Brain Contusion
• Recent NIPH Clinical Trials: A doubled-blind, crossover-RCT in T2DM to evaluate the hypoglycemic effect of P. indicus, M. charantia, P. vulgaris and A. paniculata
• Uses: Hypoglycemic agents with stronger effect than toluene sulfonylurea; used for the treatment of mild, non-insulin-dependent diabetes; Glyburide (Glibenclamide) is a sulfonylurea compound that modulates insulin production. Sulfonylureas bind to ATP-dependent K+ channels in beta cells of the pancreas, depolarizing them and stimulating the release of Ca2+, which in turn stimulates insulin production. Glyburide (Glibenclamide) is an ATP-dependent K+ channel (KIR6, KATP) and CFTR Cl- channel blocker. This compound inhibits recombinant CFTR Cl- channels (IC50 = 20 ?M). antihyperglycemic Glyburide is a second generation sulfonylurea with hypoglycemic activity. Glyburide is an antidiabetic. An ATP-dependent KIR6 and CFTR Cl- channel blocker
• Description: Glyburide (10238-21-8) is a second generation oral hypoglycemic agent. Acts via ATP-dependent K+ channel (Kir6, KATP) block.1?Inhibits Kir6 currents in the pancreas, causing an increase in intracellular Ca2+ and insulin secretion. Glyburide also inhibits recombinant CFTR Cl- channels with an IC50 of 20 μM.2?Cell permeable.
• Therapeutic Function: Oral hypoglycemic
• Clinical Use: Non-insulin dependent diabetes mellitus
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: effects enhanced by NSAIDs. Antibacterials: effects enhanced by chloramphenicol, sulphonamides, tetracyclines and trimethoprim; effects possibly enhanced by ciprofloxacin and norfloxacin; effect reduced by rifamycins. Anticoagulants: effect possibly enhanced by coumarins; also possibly changes to INR. Antifungals: concentration increased by fluconazole and miconazole and possibly voriconazole. Bosentan: increased risk of hepatoxicity - avoid. Ciclosporin: may increase ciclosporin levels. Lipid-regulating drugs: absorption reduced by colesevelam; concentration possibly increased by fluvastatin; possibly additive hypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas.

Technology Process of Glyburide

There total 19 articles about Glyburide 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: 99.0%

carbon monoxide (201230-82-2) + 4-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl azide + cyclohexylamine (108-91-8,157973-60-9) → Glibenclamid (10238-21-8)

Guidance literature:

With palladium diacetate; In acetonitrile; at 20 ℃; under 15 Torr; Schlenk technique; Sealed tube;

DOI:10.1002/anie.201600887

Reference yield: 94.0%

→ Glibenclamid (10238-21-8)

Guidance literature:

With palladium diacetate; In acetonitrile; at 20 ℃; for 12h; under 20 Torr;

Reference yield: 93.0%

5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide (16673-34-0) + cyclohexylcarbamic acid phenyl ester (56379-88-5) → Glibenclamid (10238-21-8)

Guidance literature:

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

DOI:10.1002/chem.202103196

upstream raw materials:

C₂₃H₂₈ClN₃O₅S*C₄₂H₇₀O₃₅

5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide

Cyclohexyl isocyanate

carbon monoxide

Downstream raw materials:

C₂₃H₂₈ClN₃O₅S*C₄₂H₇₀O₃₅

Refernces

• 1、 -. "Synthesis method of glibenclamide". Paragraph 0052. . Retrieved 2018/04/26.
• 2、 -. "Synthesis technology of glibenclamide". . . Retrieved 2017/08/25.