847949-49-9

Basic information

• Product Name: O-Desmethyl Gefitinib
• Synonyms: M523595;4-[(3-Chloro-4-fluorophenyl)amino]-6-[3-(4-morpholinyl)propoxy]-7-quinazolinol;O-Desmethyl Gefitinib;7-Quinazolinol, 4-[(3-chloro-4-fluorophenyl)aMino]-6-[3-(4-Morpholinyl)propoxy]-;O-Desmethyl Gefitinib D8;4-((3-chloro-4-fluorophenyl)amino)-6-(3-morpholinopropoxy)quinazolin-7-ol;Gefitinib Impurity 13;O-DesmethylGefitinibmetabolite
• CAS NO: 847949-49-9
• Molecular Formula: C₂₁H₂₂ClFN₄O₃
• Molecular Weight: 432.88
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 847949-49-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 117-120?C
• Boiling Point: 606.4°C at 760 mmHg
• Flash Point: 320.5°C
• Appearance: /
• Density: 1.386g/cm³
• Vapor Pressure: 2.68E-15mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: O-Desmethyl Gefitinib(CAS DataBase Reference)
• NIST Chemistry Reference: O-Desmethyl Gefitinib(847949-49-9)
• EPA Substance Registry System: O-Desmethyl Gefitinib(847949-49-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 847949-49-9(Hazardous Substances Data)

Usage

Description

O-Desmethyl Gefitinib, also known as D291680, is a major metabolite of Gefitinib (G304000), an antineoplastic agent. It is an isotope labeled analog of O-Desmethyl Gefitinib-d8. This yellow solid is a significant compound in the field of cancer research and treatment due to its association with Gefitinib, a drug used for treating non-small cell lung cancer.

Uses

Used in Pharmaceutical Industry:
O-Desmethyl Gefitinib is used as a metabolite for understanding the pharmacokinetics and pharmacodynamics of Gefitinib. As a major metabolite, it plays a crucial role in the metabolism and elimination of the parent drug, Gefitinib, which is an antineoplastic agent used in the treatment of non-small cell lung cancer.
Used in Cancer Research:
O-Desmethyl Gefitinib is used as a research compound for studying the mechanisms of action, resistance, and potential combination therapies involving Gefitinib. This helps researchers to better understand the drug's behavior in the body and develop strategies to overcome resistance or improve treatment outcomes for patients with non-small cell lung cancer.
Used in Drug Metabolism Studies:
O-Desmethyl Gefitinib is used as a reference compound in drug metabolism studies. It aids researchers in identifying and characterizing the enzymes and pathways involved in the biotransformation of Gefitinib, which can provide insights into individual variability in drug response and the potential for drug-drug interactions.
Used in Quality Control and Analytical Methods Development:
O-Desmethyl Gefitinib is used as a quality control material and a reference standard in the development and validation of analytical methods for the quantification of Gefitinib and its metabolites in biological samples. This ensures the accuracy, precision, and reliability of the assays used in clinical and research settings to monitor drug levels and assess treatment efficacy.

InChI:InChI=1/C21H22ClFN4O3/c22-16-10-14(2-3-17(16)23)26-21-15-11-20(19(28)12-18(15)24-13-25-21)30-7-1-4-27-5-8-29-9-6-27/h2-3,10-13,28H,1,4-9H2,(H,24,25,26)

Upstream product

• 184475-35-2 gefitinib 
• 199327-61-2 7-methoxy-6-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one 
• 7357-67-7 4-(3-chloropropyl)morpholine 
• 675126-28-0 4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 675126-26-8 2-nitro-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 246512-44-7 2-amino-4-methoxy-5-[3-(morpholin-4-yl)propoxy]benzamide 
• 621-59-0 isovanillin 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 199327-59-8 4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 87687-75-0 methyl 4-(benzyloxy)-3-hydroxybenzoate 

Downstream Products

• 869475-51-4 trifluoro-methanesulfonic acid 4-(3-chloro-4-fluoro-phenylamino)-6-(3-morpholin-4-yl-propoxy)-quinazolin-7-yl ester 

Relevant articles and documents

One-step radiosynthesis of18F-IRS: A novel radiotracer targeting mutant EGFR in NSCLC for PET/CT imaging

EGFR (epidermal growth factor receptor) targeted therapy has shown great success in clinical comparing with chemotherapy in EGFR mutation NSCLCs. Such as, gefitinib, first generation EGFR TKI, has obviously prolonged the FPS (progression free survival) of the subgroup of patients, but to those who did not get a certain mutation in EGFR kinase domain, the outcome is poor. In view of this situation, scientists have synthesized many radiotracers for selecting the right people by PET/CT imaging to NSCLC TKI therapy. In this study, we developed a novel PET radiotracer18F-IRS in one-step with a radio yield 20% (non-corrected), radiochemistry > 98.5%, specific activity > 105G Bq/μmol, the pharmacokinetics and capacity of the tracer binding to mutant EGFR were evaluated both in vitro and in vivo.

EGFR (epidermal growth factor receptor) kinase inhibitor and application thereof in preparation of anti-cancer drugs

The invention discloses an EGFR (epidermal growth factor receptor) kinase inhibitor and application thereof in preparation of anti-cancer drugs, the EGFR kinase inhibitor can effectively improve EGFRTKI acquired drug resistance caused by SQSTM1 accumulati

OXOINDOLINE DERIVATIVES AS PROTEIN FUNCTION MODULATORS

The present invention provides chimeric compounds of formula (II) that modulate protein function, to restore protein homeostasis, including cytokine, aiolos, and/or ikaros activity, TNF-alpha activity, CKl-alpha activity and cell-cell adhesion. The invention provides methods of modulating protein-mediated diseases, such as cytokine-mediated diseases, disorders, conditions, or responses. Compositions, including in combination with other cytokine and inflammatory mediators, are provided. Methods of treatment, amelioration, or prevention of protein-mediated diseases, disorders, and conditions, such as cytokine-mediated diseases, disorders, and conditions, including inflammation, fibromyalgia, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, psoriasis, psoriatic arthritis, inflammatory bowel diseases, Crohn's disease, ulcerative colitis, uveitis, inflammatory lung diseases, chronic obstructive pulmonary disease, Alzheimer's disease, organ transplant rejection, and cancer, are provided.