Imatinib Mesylate

Base Information

• Chemical Name: Imatinib Mesylate
• CAS No.: 220127-57-1
• Molecular Formula: C29H31N7O^.CH4O3S
• Molecular Weight: 589.71
• Hs Code.: 29350090
• European Community (EC) Number: 606-892-3
• NSC Number: 716051
• UNII: 8A1O1M485B
• DSSTox Substance ID: DTXSID9040502
• Wikidata: Q27114666
• NCI Thesaurus Code: C1687
• RXCUI: 284924
• ChEMBL ID: CHEMBL1642
• Mol file: 220127-57-1.mol

Synonyms:alpha-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-tolu-p-toluidide;CGP 57148;CGP-57148;CGP57148;CGP57148B;Gleevec;Glivec;imatinib;imatinib mesylate;imatinib methanesulfonate;Mesylate, Imatinib;Methanesulfonate, Imatinib;ST 1571;ST1571;STI 571;STI-571;STI571

Chemical Property of Imatinib Mesylate

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 214-224°C
• Boiling Point: 754.9 °C at 760 mmHg
• Flash Point: 410.3 °C
• PSA: 149.03000
• Density: 0.858g/mLat 25°C(lit.)
• LogP: 5.19690
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble10mg/mL, clear
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 589.24712380
• Heavy Atom Count: 42
• Complexity: 799

Purity/Quality:

99% ^*data from raw suppliers

Gleevec(ImatinibMesylate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5.CS(=O)(=O)O
• Recent ClinicalTrials: Imatinib for Pain in Sickle Cell Anemia
• Recent EU Clinical Trials: A phase III, multi-center, open-label, randomized study of oral asciminib versus Investigator selected TKI in patients with newly diagnosed Philadelphia Chromosome Positive Chronic Myelogenous Leukemia in Chronic Phase
• Recent NIPH Clinical Trials: Phase II study of imatinib mesylate for treatment of Philadelphia Chromosome-positive acute lymphoblastic leukemia (Ph+ ALL) in children: A Japanese Cooperative Trial
• Molecular Formula and Drug: Imatinib mesylate (IMAT) is a drug used to treat chronic myeloid leukemia (CML) and gastrointestinal stromal tumors. Its molecular formula is 4-[(4-methylpiperazin-1-yl) methyl]-N- [4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl) amino] phenyl]benzamide. IMAT inhibits tyrosine kinase, altering the management of tumors resistant to cytotoxic chemotherapy.
• Mechanism of Action: IMAT functions as a tyrosine kinase inhibitor, specifically targeting BCR-ABL and c-KIT kinases. It inhibits tumor growth and induces apoptosis in cancer cells by impeding the activity of various tyrosine kinases involved in tumor development and blood vessel formation, including PDGFR and VEGFR.
• Metabolism: IMAT is primarily metabolized by the enzyme CYP3A4. Patients may exhibit diverse circulating concentrations of IMAT depending on the dosage, highlighting the importance of monitoring plasma IMAT concentrations for clinical outcomes.
• Potential Therapeutic Uses: In addition to its anticancer properties, IMAT has shown potential anti-Alzheimer's activity, leading to its repurposing for Alzheimer's disease treatment. Liposomal delivery of IMAT via the nose-to-brain route has demonstrated improved drug deposition and residence time in the brain compared to oral and intranasal administration.
• Effectiveness and Safety: IMAT has demonstrated effectiveness as a treatment for colon cancer in preclinical studies and clinical trials. However, its standalone efficacy is limited by the development of drug resistance and adverse reactions such as edema, nausea, and vomiting.
• Nanoparticle-Mediated Delivery: Nanoparticle-based drug delivery systems have been developed to enhance the effectiveness and safety of IMAT. These systems aim to address concerns such as drug resistance and adverse reactions associated with conventional IMAT therapy.
• General Description: Imatinib mesylate, also known as STI-571 or by other names such as Veenat, is a tyrosine kinase inhibitor primarily used to treat cancers driven by Bcr-Abl and c-KIT, such as chronic myeloid leukemia (CML) and gastrointestinal stromal tumors (GISTs). It functions by competitively binding to the ATP-binding site of these kinases, thereby inhibiting their activity and blocking downstream signaling pathways that promote cell proliferation. Imatinib mesylate and its analogs have been explored for their potential in PET imaging to visualize kinase expression and assess therapeutic response, highlighting its dual role as both a therapeutic agent and a diagnostic tool.

Technology Process of Imatinib Mesylate

There total 23 articles about Imatinib Mesylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.89%

methanesulfonic acid (75-75-2,98527-29-8) + imatinib (152459-95-5) → imatinib mesylate (220127-57-1)

Guidance literature:

In acetone; at 55 - 60 ℃; for 2h; Concentration; Temperature; Time;

Reference yield: 99.6%

methanesulfonic acid (75-75-2,98527-29-8) + imatinib (152459-95-5) → imatinib mesylate (220127-57-1)

Guidance literature:

In isopropyl alcohol; at 20 - 80 ℃; Product distribution / selectivity; Reflux;

Reference yield: 91.0%

methanesulfonic acid (75-75-2,98527-29-8) + imatinib (152459-95-5) → 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-[(4-pyridin-3-yl)pyrimidin-2-ylamino]phenyl]benzamide dimesylate (220127-57-1)

Guidance literature:

In water; isopropyl alcohol; at 20 ℃;

upstream raw materials:

methanesulfonic acid

imatinib

4-((4-methylpiperazin-1-yl)methyl)benzamide

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine

Refernces

Imatinib analogs as potential agents for PET imaging of Bcr-Abl and c-KIT expression at a kinase level

10.1016/j.bmc.2013.10.040

The research focused on the synthesis and evaluation of imatinib mesylate (STI-571) analogs as potential agents for PET imaging of Bcr-Abl and c-KIT expression at the kinase level. The study involved molecular modeling to predict binding configurations, followed by the synthesis of STI-571 and its analogs using various reactants such as 2-methyl-5-nitroaniline, cyanamide, and 3-acetylpyridine derivatives. Radiolabeling with [18F] and [131I] was performed to prepare PET imaging agents. In vitro kinase assays were conducted to assess the potency of the analogs in inhibiting Bcr-Abl and c-KIT kinase activities. The uptake rates of [18F]-STI-571 in K562 cells (expressing Abl) and U87WT cells (overexpressing c-KIT) were measured and compared with those in U87 cells. PET scans were conducted on tumor-bearing mice to visualize tumor uptake and contrast. The research utilized various analytical techniques, including HPLC, MS, NMR, and radio-TLC, to monitor reactions, assess radiochemical purity, and characterize compounds. The results showed that the [18F]-STI-571 analog could serve as a marker for sensitivity to Bcr-Abl and c-KIT inhibitors, potentially aiding in patient selection for targeted therapies.

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