404844-02-6

Basic information

• Product Name: N-Desmethyl Imatinib
• Synonyms: CGP-74588;N-[4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-4-(1-piperazinylmethyl)-benzamide;Norimatinib;STI 509-00;N-{4-Methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}-4-(piperazin-1-ylmethyl)benzamide;DesMethyl IMatinib;DesMethyl IMatinib-d8;iMatinib related substance A
• CAS NO: 404844-02-6
• Molecular Formula: C28H29N7O
• Molecular Weight: 479.585
• EINECS: 1592732-453-0
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Tyrosine Kinase Inhibitors;Metabolite Reference Standard;Isotopically Labeled Pharmaceutical Reference Standard
• Mol File: 404844-02-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 99-101°C
• Appearance: Off-white to pale-yellow solid
• Density: 1.269 g/cm³
• Refractive Index: 1.676
• Storage Temp.: -20°C Freezer
• PKA: 13.28±0.70(Predicted)
• CAS DataBase Reference: N-Desmethyl Imatinib(CAS DataBase Reference)
• NIST Chemistry Reference: N-Desmethyl Imatinib(404844-02-6)
• EPA Substance Registry System: N-Desmethyl Imatinib(404844-02-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 404844-02-6(Hazardous Substances Data)

Usage

Description

N-desmethyl Imatinib is a major active metabolite of imatinib , an anticancer agent that selectively targets tyrosine kinases, including Bcr-ABL, platelet-derived growth factor receptor (PDGFR), and KIT. N-desmethyl Imatinib is formed when imatinib undergoes demethylation by the cytochrome P450 (CYP) isomer CYP3A4. N-desmethyl Imatinib has the same in vitro potency at Bcr-ABL kinase as imatinib (IC50 = 38 nM for both) but is only present in plasma at 10-15% of the levels of imatinib, indicating the majority of the anticancer activity can be attributed to the parent compound.

Uses

Different sources of media describe the Uses of 404844-02-6 differently. You can refer to the following data:
1. A metabolite of Gleevec, a tyrosine kinase inhibitor which is highly specific for BCR-ABL, the enzyme associated with chronic myelogenous leukemia (CML) and certain forms of acute lymphoblastic leukemia (ALL)
2. aminoglycoside antibiotic similar to gentamycin, toxic to bacterial, yeast, higher plant and mammalian cells and to protozoans and helminthes
3. anti-epileptic

InChI:InChI=1/C28H29N7O/c1-20-4-9-24(17-26(20)34-28-31-12-10-25(33-28)23-3-2-11-30-18-23)32-27(36)22-7-5-21(6-8-22)19-35-15-13-29-14-16-35/h2-12,17-18,29H,13-16,19H2,1H3,(H,32,36)(H,31,33,34)

Upstream product

• 120465-56-7 4-(dimethoxymethyl)benzoic acid 
• 619-66-9 4-Carboxybenzaldehyde 
• 1076199-23-9 tert-butyl 4-(4-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamoyl)benzyl)piperazine-1-carboxylate 
• 479353-63-4 (4-(4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)benzoic acid 
• 152460-10-1 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 350-03-8 methyl-3-pyridylketone 
• 152460-09-8 N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine 
• 66521-66-2 4-pyridin-3-ylpyrimidin-2-ylamine 
• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 110-85-0 piperazine 
• 404844-10-6 4-(сhloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide hydrochloride 
• 876-08-4 p-(chloromethyl)benzoyl chloride 
• 404844-11-7 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide 

Downstream Products

• 404844-03-7 N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]-4-(1-piperazinylmethyl)benzamide methanesulphonate 
• 1134803-18-1 4-[[4-(methyl-d3)-1-piperazinyl]methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide 

Relevant articles and documents

Haptens, antigens and antibodies of imatinib and N-demethylated imatinib and application thereof

The invention relates to the technical field of immunological detection, and particularly discloses haptens, antigens and antibodies of imatinib and N-demethylated imatinib and application of the haptens, the antigens and the antibodies, the structure of

Development of Gleevec Analogues for Reducing Production of β-Amyloid Peptides through Shifting β-Cleavage of Amyloid Precursor Proteins

Imatinib mesylate, 1a, inhibits production of β-amyloid (Aβ) peptides both in cells and in animal models. It reduces both the β-secretase and γ-secretase cleavages of the amyloid precursor protein (APP) and mediates a synergistic effect, when combined with a β-secretase inhibitor, BACE IV. Toward developing more potent brain-permeable leads, we have synthesized and evaluated over 75 1a-analogues. Several compounds, including 2a-b and 3a-c, inhibited production of Aβ peptides with improved activity in cells. These compounds affected β-secretase cleavage of APP similarly to 1a. Compound 2a significantly reduced production of the Aβ42 peptide, when administered (100 mg/kg, twice daily by oral gavage) to 5 months old female mice for 5 days. A combination of compound 2a with BACE IV also reduced Aβ levels in cells, more than the additive effect of the two compounds. These results open a new avenue for developing treatments for Alzheimer's disease using 1a-analogues.

Enantioselective synthesis of α-secondary and α-tertiary piperazin-2- Ones and piperazines by catalytic asymmetric allylic alkylation

The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2- ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.