(R)-Pioglitazone
Overview
Description
®-Pioglitazone is a chiral compound and a member of the thiazolidinedione class of drugs. It is primarily used as an antidiabetic agent, specifically for the treatment of type 2 diabetes mellitus. The compound works by improving insulin sensitivity in patients, thereby helping to control blood sugar levels.
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of ®-Pioglitazone involves several steps, starting from the appropriate chiral precursors. One common method includes the use of chiral catalysts to ensure the correct stereochemistry. The reaction conditions typically involve controlled temperatures and pH levels to maintain the integrity of the chiral center.
Industrial Production Methods
In industrial settings, the production of ®-Pioglitazone is scaled up using optimized synthetic routes that ensure high yield and purity. This often involves the use of large-scale reactors and continuous monitoring of reaction conditions to maintain consistency.
Chemical Reactions Analysis
Types of Reactions
®-Pioglitazone undergoes various chemical reactions, including:
Oxidation: This reaction can modify the functional groups on the molecule, potentially altering its activity.
Reduction: Used to convert certain functional groups into more reactive forms.
Substitution: Commonly involves the replacement of one functional group with another, which can be useful in modifying the compound for different applications.
Common Reagents and Conditions
Oxidizing Agents: Such as potassium permanganate or hydrogen peroxide.
Reducing Agents: Like sodium borohydride or lithium aluminum hydride.
Substitution Reagents: Including halogens and nucleophiles.
Major Products
The major products formed from these reactions depend on the specific reagents and conditions used. For example, oxidation might yield hydroxylated derivatives, while substitution could introduce new functional groups.
Scientific Research Applications
®-Pioglitazone has a wide range of applications in scientific research:
Chemistry: Used as a model compound for studying chiral synthesis and reaction mechanisms.
Biology: Investigated for its effects on cellular metabolism and insulin signaling pathways.
Medicine: Primarily used in the treatment of type 2 diabetes, but also explored for potential benefits in other metabolic disorders.
Industry: Utilized in the development of new antidiabetic drugs and formulations.
Mechanism of Action
®-Pioglitazone exerts its effects by activating the peroxisome proliferator-activated receptor gamma (PPARγ). This receptor plays a crucial role in the regulation of glucose and lipid metabolism. By binding to PPARγ, ®-Pioglitazone enhances the transcription of insulin-responsive genes, leading to improved insulin sensitivity and glucose uptake in tissues.
Comparison with Similar Compounds
Similar Compounds
Rosiglitazone: Another thiazolidinedione with similar antidiabetic properties.
Troglitazone: An older compound that was withdrawn from the market due to safety concerns.
Ciglitazone: A less commonly used thiazolidinedione.
Uniqueness
®-Pioglitazone is unique in its chiral nature, which can influence its pharmacokinetics and pharmacodynamics. Its specific interaction with PPARγ and the resulting effects on insulin sensitivity make it a valuable option for the treatment of type 2 diabetes.
Properties
CAS No. |
959687-65-1 |
|---|---|
Molecular Formula |
C19H20N2O3S |
Molecular Weight |
356.4 g/mol |
IUPAC Name |
(5R)-5-[[4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione |
InChI |
InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)/t17-/m1/s1 |
InChI Key |
HYAFETHFCAUJAY-QGZVFWFLSA-N |
Isomeric SMILES |
CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)C[C@@H]3C(=O)NC(=O)S3 |
Canonical SMILES |
CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3 |
Origin of Product |
United States |
Synthesis routes and methods I
Procedure details
Synthesis routes and methods II
Procedure details
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