Chlorpropamide-d4
Overview
Description
Chlorpropamide-d4 is a deuterated form of chlorpropamide, an antidiabetic drug belonging to the sulfonylurea class of organic compounds. It is used primarily for the treatment of type 2 diabetes mellitus. The deuterated form, this compound, is often used in scientific research as an internal standard in mass spectrometry due to its stable isotopic labeling .
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of Chlorpropamide-d4 involves the incorporation of deuterium atoms into the chlorpropamide molecule. This can be achieved through various methods, including catalytic hydrogen-deuterium exchange reactions. The reaction typically involves the use of deuterium gas (D2) in the presence of a catalyst such as palladium on carbon (Pd/C) under controlled conditions .
Industrial Production Methods
Industrial production of this compound follows similar synthetic routes but on a larger scale. The process involves stringent quality control measures to ensure the purity and isotopic labeling of the final product. The use of high-performance liquid chromatography (HPLC) and mass spectrometry is common in the quality assessment of this compound .
Chemical Reactions Analysis
Types of Reactions
Chlorpropamide-d4, like its non-deuterated counterpart, undergoes various chemical reactions, including:
Oxidation: this compound can be oxidized to form sulfoxides and sulfones.
Reduction: Reduction reactions can convert the sulfonyl group to a sulfide.
Substitution: Nucleophilic substitution reactions can occur at the chloro group, leading to the formation of various derivatives.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include hydrogen peroxide (H2O2) and potassium permanganate (KMnO4).
Reduction: Reducing agents such as lithium aluminum hydride (LiAlH4) are used.
Substitution: Nucleophiles like sodium methoxide (NaOCH3) can be used for substitution reactions.
Major Products Formed
Oxidation: Sulfoxides and sulfones.
Reduction: Sulfides.
Substitution: Various substituted derivatives depending on the nucleophile used.
Scientific Research Applications
Chlorpropamide-d4 is extensively used in scientific research, particularly in the fields of:
Chemistry: As an internal standard in mass spectrometry for the quantification of chlorpropamide and related compounds.
Biology: In studies involving the metabolism and pharmacokinetics of chlorpropamide.
Medicine: In research focused on the treatment of diabetes and the development of new antidiabetic drugs.
Industry: In the quality control and validation of pharmaceutical formulations containing chlorpropamide
Mechanism of Action
Chlorpropamide-d4, like chlorpropamide, acts by stimulating the release of insulin from pancreatic beta cells. It binds to ATP-sensitive potassium channels on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. This depolarization opens voltage-gated calcium channels, leading to an influx of calcium ions and subsequent insulin release .
Comparison with Similar Compounds
Similar Compounds
Tolbutamide: Another first-generation sulfonylurea with a shorter duration of action.
Glipizide: A second-generation sulfonylurea with a more potent effect and shorter half-life.
Glyburide: A second-generation sulfonylurea with a longer duration of action compared to glipizide.
Uniqueness
Chlorpropamide-d4 is unique due to its deuterated nature, which makes it particularly useful as an internal standard in analytical chemistry. Its long half-life and potent insulin-releasing effect make it distinct among first-generation sulfonylureas .
Properties
IUPAC Name |
1-(4-chloro-2,3,5,6-tetradeuteriophenyl)sulfonyl-3-propylurea |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)/i3D,4D,5D,6D |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
RKWGIWYCVPQPMF-LNFUJOGGSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
[2H]C1=C(C(=C(C(=C1S(=O)(=O)NC(=O)NCCC)[2H])[2H])Cl)[2H] |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H13ClN2O3S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
280.77 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Synthesis routes and methods
Procedure details
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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