Glimepiride

Base Information

• Chemical Name: Glimepiride
• CAS No.: 93479-97-1
• Molecular Formula: C24H34N4O5S
• Molecular Weight: 490.624
• Hs Code.: 2935904000
• Mol file: 93479-97-1.mol

Synonyms:glimepirid; hoe490

Chemical Property of Glimepiride

Chemical Property:

• Appearance/Colour: white cyrstalline solid
• Melting Point: 212.2-214.5 °C
• Refractive Index: 1.599
• PKA: 5.10±0.10(Predicted)
• PSA: 133.06000
• Density: 1.29 g/cm³
• LogP: 5.26540
• Storage Temp.: Room temp
• Solubility.: DMSO: >10 mg/mL
• Water Solubility.: DMSO: >10 mg/mL

Purity/Quality:

99.5%min, ^*data from raw suppliers

Glimepiride ^*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

MSDS Files:

SDS file from LookChem

Useful:

• Classification and Structure: Glimepiride is a third-generation sulfonylurea used in the treatment of type II diabetes mellitus. It shares a similar fundamental structure with glibenclamide and stimulates insulin secretion primarily by inhibiting the Sur1-regulated ATP-sensitive potassium channel.
• Pharmacokinetics and Pharmacodynamics: Glimepiride exhibits high hypoglycemic efficacy and low systemic toxicity. It belongs to class II drugs according to the Biopharmaceutical Classification System (BCS), characterized by low solubility and high permeability. However, its poor water solubility leads to challenges in oral pharmaceutical preparation, dissolution profile, and bioavailability.
• Enhancement Techniques: Various techniques are employed to enhance the solubility of poorly water-soluble drugs like glimepiride. These include prodrug formation, salt formation, crystal engineering, and solid dispersion methods using water-soluble polymers. Solid dispersion is particularly effective in improving aqueous solubility.
• Physical Properties: Glimepiride does not undergo polymorphic transformations during processing, as indicated by studies using techniques like differential scanning calorimetry (DSC) and FT-IR spectroscopy. However, milling processes can induce changes in the hydrogen bonding patterns of glimepiride crystals.
• Mechanism of Action: Glimepiride stimulates insulin release from beta cells in the pancreas and enhances the activity of intracellular insulin receptors. It undergoes slow gastrointestinal dissolution and exhibits inter-personal variations, affecting its bioavailability.
• Adverse Effects and Strategies: Severe hypoglycemia can occur with large doses of glimepiride due to variations in absorption. Strategies such as inclusion complexes, solid dispersion, and micronization techniques have been employed to enhance dissolution, oral absorption, and bioavailability. Additionally, formulations like sublingual tablets and sustained-release tablets aim to improve drug absorption profiles and consistency.

Technology Process of Glimepiride

There total 16 articles about Glimepiride 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: 95.0%

C19H25N3O6S + trans-4-methylcyclohexanamine (2523-55-9) → glimepiride (93479-97-1)

Guidance literature:

dmap; In toluene; Heating / reflux;

Reference yield: 94.5%

(1R,4R)-1-isocyanato-4-methylcyclohexane (32175-00-1) + N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide (119018-29-0) → glimepiride (93479-97-1)

Guidance literature:

In tert-butyl methyl ether; cyclohexanone; at 30 ℃; for 10h; Temperature;

Reference yield: 85.0%

phenyl ((1r,4r)-4-methylcyclohexyl)carbamate + N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide (119018-29-0) → glimepiride (93479-97-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 5h; Reflux;

DOI:10.1055/s-0036-1590836

upstream raw materials:

(1R,4R)-1-isocyanato-4-methylcyclohexane

N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide

3-ethyl-4-methyl-3-pyrrolin-2-one

phenethyl isocyanate

Downstream raw materials:

carboxyglimepiride

DTPA-glimepiride

3-ethyl-2,5-dihydro-4-methyl-N-[2[4-[[[(trans-4-methylcyclohexyl)amino]carbonyl]aminosulfonyl]phenyl]ethyl]-2,2-difluoro-1H-pyrrole-1-N-carboxamide

C₂₄H₃₂N₄O₇S

Refernces

• 1、 -. "Process for synthesizing glimepiride raw material medicine". Paragraph 0103-0106. . Retrieved 2018/09/08.
• 2、 Tanwar, Dinesh Kumar,Surendrabhai, Vaghela Ravikumar,Gill, Manjinder Singh. "An Efficient and Practical Process for the Synthesis of Glimepiride". . p. 2495 - 2498. Retrieved 2017/10/06.