Anastrozole EP Impurity I
Overview
Description
Scientific Research Applications
Anastrozole EP Impurity I is extensively used in pharmaceutical research for:
Product Development: It helps in the development of Anastrozole formulations by identifying and quantifying impurities.
Quality Control: Ensures the purity and safety of Anastrozole products.
Method Validation: Used in the validation of analytical methods for detecting impurities.
Stability Studies: Assesses the stability of Anastrozole under various conditions.
Genotoxic Potential Assessment: Evaluates the potential genotoxicity of impurities.
Mechanism of Action
Target of Action
Anastrozole EP Impurity I, also known as UNII-UA6KB3ICZ1, is a derivative of Anastrozole . Anastrozole is a third-generation non-steroidal aromatase inhibitor . Aromatase is the primary target of Anastrozole, and it plays a crucial role in the biosynthesis of estrogens from androgens .
Mode of Action
This compound, similar to Anastrozole, is likely to act as a potent and selective aromatase inhibitor . By inhibiting aromatase, the conversion of androstenedione to estrone, and testosterone to estradiol, is prevented . This results in a decrease in circulating estrogen levels, which is beneficial in the treatment of estrogen-responsive conditions.
Preparation Methods
Synthetic Routes and Reaction Conditions: The reaction conditions typically involve the use of chloromethylating agents and nitrile sources under controlled temperatures and pressures .
Industrial Production Methods: Industrial production of Anastrozole EP Impurity I follows similar synthetic routes but on a larger scale. The process involves stringent quality control measures to ensure the purity and consistency of the compound. The production is carried out in compliance with regulatory guidelines to meet pharmacopeial standards .
Chemical Reactions Analysis
Types of Reactions: Anastrozole EP Impurity I undergoes various chemical reactions, including:
Substitution Reactions: The chloromethyl group can be substituted with other nucleophiles.
Oxidation Reactions: The compound can be oxidized to introduce additional functional groups.
Reduction Reactions: The nitrile groups can be reduced to amines under specific conditions.
Common Reagents and Conditions:
Substitution: Nucleophiles such as amines or thiols in the presence of a base.
Oxidation: Oxidizing agents like potassium permanganate or chromium trioxide.
Reduction: Reducing agents such as lithium aluminum hydride or catalytic hydrogenation.
Major Products:
Substitution: Derivatives with different functional groups replacing the chloromethyl group.
Oxidation: Compounds with additional oxygen-containing functional groups.
Reduction: Amines derived from the reduction of nitrile groups.
Comparison with Similar Compounds
Anastrozole EP Impurity A: 2,2′-[5-(Bromomethyl)benzene-1,3-diyl]bis(2-methylpropanenitrile)
Anastrozole EP Impurity B: 2,2′-[5-(Hydroxymethyl)benzene-1,3-diyl]bis(2-methylpropanenitrile)
Anastrozole EP Impurity C: 2,2′-[5-(Methoxymethyl)benzene-1,3-diyl]bis(2-methylpropanenitrile)
Uniqueness: Anastrozole EP Impurity I is unique due to the presence of a chloromethyl group, which makes it distinct in its reactivity and the types of reactions it undergoes. This uniqueness is essential for the comprehensive analysis of Anastrozole and its related impurities .
Properties
IUPAC Name |
2-[3-(chloromethyl)-5-(2-cyanopropan-2-yl)phenyl]-2-methylpropanenitrile |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C15H17ClN2/c1-14(2,9-17)12-5-11(8-16)6-13(7-12)15(3,4)10-18/h5-7H,8H2,1-4H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
HSNGPKBBTHINTG-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)(C#N)C1=CC(=CC(=C1)CCl)C(C)(C)C#N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C15H17ClN2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID50598265 |
Source
|
| Record name | 2,2'-[5-(Chloromethyl)-1,3-phenylene]bis(2-methylpropanenitrile) | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50598265 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
260.76 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
120511-91-3 |
Source
|
| Record name | 5-(Chloromethyl)-α1,α1,α3,α3-tetramethyl-1,3-benzenediacetonitrile | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=120511-91-3 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | 2-(3-(Chloromethyl)-5-(2-cyanopropan-2-yl)phenyl)-2-methylpropanenitrile | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0120511913 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | 2,2'-[5-(Chloromethyl)-1,3-phenylene]bis(2-methylpropanenitrile) | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID50598265 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 2-(3-(CHLOROMETHYL)-5-(2-CYANOPROPAN-2-YL)PHENYL)-2-METHYLPROPANENITRILE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/UA6KB3ICZ1 | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
Synthesis routes and methods
Procedure details
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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