Diamicron

Base Information

• Chemical Name: Diamicron
• CAS No.: 21187-98-4
• Molecular Formula: C15H21N3O3S
• Molecular Weight: 323.416
• Hs Code.: 29350090
• UNII: G4PX8C4HKV
• Wikidata: Q63390542
• NCI Thesaurus Code: C87618
• Mol file: 21187-98-4.mol

Synonyms:Diabrezide;Diaglyk;Diaikron;Diamicron;Gen Gliclazide;Gen-Gliclazide;Gliclazide;Gliklazid;Glyade;Glyclazide;Novo Gliclazide;Novo-Gliclazide;S 1702;S 852;S-1702;S-852;S1702;S852

Chemical Property of Diamicron

Chemical Property:

• Appearance/Colour: white cyrstalline solid
• Melting Point: 163-169 °C(lit.)
• Refractive Index: 1.623
• PKA: 6.07±0.10(Predicted)
• PSA: 86.89000
• Density: 1.35 g/cm³
• LogP: 3.43030
• Storage Temp.: -20°C Freezer
• Solubility.: methylene chloride: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 323.13036271
• Heavy Atom Count: 22
• Complexity: 497

Purity/Quality:

99.0% ^*data from raw suppliers

Gliclazide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2C[C@H]3CCC[C@H]3C2
• Recent ClinicalTrials: Clinical Bioequivalence Study on Two Gliclazide 80mg Tablet Formulations
• Recent EU Clinical Trials: Dipeptidyl peptidase-4 Inhibition in Psoriasis patients with diabetes (DIP): A Randomized Clinical Trial.
• Description: Gliclazide is an oral antihyperglycemic agent used for the treatment of diabetes mellitus type II. It belongs to the sulfonylurea class of insulin secretagogues, which stimulates β cells of the pancreas to release insulin. Gliclazide binds to the β cell sulfonyl urea receptor (SUR1), further blocking the ATP sensitive potassium channels. Therefore, the potassium efflux substantially decreases, causing depolarization of the β cells. Then the voltage-dependent calcium channels in the β cell are open, resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules. Recent studies have also shown that gliclazide can effectiveimprove anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes and protect pancreatic beta-cells from damage by hydrogen peroxide.
• Uses: Gliclazide is an oral hypoglycemic agent used to treat non-insulin-dependent diabetes mellitus.Treatment of diabetes associated with obesity or vascular disease, for adults with type 2 diabetes.Diabetes is a chronic (long-lasting) health condition that affects how your body turns food into energy. Gliclazide reduces blood glucose levels by stimulating insulin secretion from the β-cells of the islets of Langerhans.
• 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 and miconazole and possibly voriconazole - avoid with miconazole. Lipid-regulating drugs: possibly additive hypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas.When gliclazide is used with nonsteroidal anti-inflammatory drug (especially salicylates), sulfa antibiotic, double coumarin anticoagulants, monoamine oxidase inhibitors, β-blockers, tetracycline, chloramphenicol, dicyclohexyl B piperidine, clofibrate, ethanol and other drugs, its dosage should be reduced to avoid hypoglycemia reaction.

Technology Process of Diamicron

There total 25 articles about Diamicron 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: 91.9%

N-(hexahydrocyclopenta[c]pyrrole-2-(1H)-yl)aminocarbonyl chloride + toluene-4-sulfonamide (70-55-3) → gliclazide (21187-98-4)

Guidance literature:

With N,N-dimethyl-formamide; In toluene; for 2h; Reagent/catalyst; Reflux;

Reference yield: 91.0%

toluene-4-sulfonamide (70-55-3) + phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamate (700359-75-7) → gliclazide (21187-98-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; acetonitrile; at 80 ℃; for 8h; Temperature; Time; Flow reactor;

DOI:10.1055/a-1664-2282

Reference yield: 87.0%

toluene-4-sulfonamide (70-55-3) + N-amino-aza-3-bicyclo<3.3.0>octane (54528-00-6) + phenyl chloroformate (1885-14-9) → gliclazide (21187-98-4)

Guidance literature:

N-amino-aza-3-bicyclo<3.3.0>octane; phenyl chloroformate; With tributyl-amine; In chloroform; at 0 ℃; for 0.00833333h; Flow reactor;

toluene-4-sulfonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; acetonitrile; at 80 ℃; for 8h; Temperature; Time; Flow reactor;

DOI:10.1055/a-1664-2282

upstream raw materials:

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride

4-toluenesulfonylurea

N-amino-1,2-cyclopentanedicarboximide

toluene-4-sulfonamide

Downstream raw materials:

toluene-4-sulfonamide

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride

hydrogen cyanide

Refernces

• 1、 -. "Preparation method of gliclazide". Paragraph 0099-0101. . Retrieved 2021/10/27.
• 2、 -. "Sulfonylurea compound synthesis method". Paragraph 0028; 0056-0067. . Retrieved 2021/11/26.