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Imatinib mesylate

CAS No.
220127-57-1
Chemical Name:
Imatinib mesylate
Synonyms
GLEEVEC;GLIVEC;Imatinib (Glivec);Gleevac;STI-571;CGP54148B;CGP 57148;CGP-57148B;Genfatinib;tinib Mesylate
CBNumber:
CB7173646
Molecular Formula:
C30H35N7O4S
Molecular Weight:
589.71
MDL Number:
MFCD04307699
MOL File:
220127-57-1.mol
MSDS File:
SDS
Last updated:2023-12-06 17:20:55

Imatinib mesylate Properties

Melting point 214-224°C
storage temp. 2-8°C
solubility H2O: soluble10mg/mL, clear
form White solid
color white to beige
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or water may be stored at -20°C for up to 3 months.
InChIKey YLMAHDNUQAMNNX-UHFFFAOYSA-N
SMILES C(NC1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1)(=O)C1=CC=C(CN2CCN(C)CC2)C=C1.CS(O)(=O)=O
CAS DataBase Reference 220127-57-1(CAS DataBase Reference)
FDA UNII 8A1O1M485B
NCI Dictionary of Cancer Terms Gleevec; imatinib mesylate; STI571
NCI Drug Dictionary Gleevec

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Warning
Hazard statements  H361d
Precautionary statements  P201-P202-P280-P308+P313-P405-P501
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  CV5520550
HS Code  29350090
NFPA 704
0
2 0

Imatinib mesylate price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML1027 Imatinib mesylate ≥98% (HPLC) 220127-57-1 10mg $43.5 2024-03-01 Buy
Sigma-Aldrich SML1027 Imatinib mesylate ≥98% (HPLC) 220127-57-1 100mg $149 2024-03-01 Buy
Sigma-Aldrich 5.04595 Bcr-abl Inhibitor IV, Imatinib - CAS 220127-57-1 - Calbiochem 220127-57-1 50mg $155 2024-03-01 Buy
TCI Chemical I0936 Imatinib Mesylate >98.0%(HPLC) 220127-57-1 100mg $54 2024-03-01 Buy
TCI Chemical I0936 Imatinib Mesylate >98.0%(HPLC) 220127-57-1 1g $314 2024-03-01 Buy
Product number Packaging Price Buy
SML1027 10mg $43.5 Buy
SML1027 100mg $149 Buy
5.04595 50mg $155 Buy
I0936 100mg $54 Buy
I0936 1g $314 Buy

Imatinib mesylate Chemical Properties,Uses,Production

a small-molecule inhibitor

Imatinib mesylate (also called Gleevec) is a small-molecule inhibitor of the fusion protein Bcr-Abl, the causal agent in chronic myelogenous leukemia.
As an inhibitor of PDGFR, imatinib mesylate appears to have utility in the treatment of a variety of dermatological diseases. Imatinib has been reported to be an effective treatment for FIP1L1-PDGFRalpha+ mast cell disease, hypereosinophilic syndrome, and dermatofibrosarcoma protuberans.

Description

In May 2001, the FDA approved imatinib as a new cancer drug after a record review time of just 2.5 months. Imatinib was launched as Gleevec in the US for chronic myelogenous leukemia (CML) in blast crisis, accelerated phase or chronic phase after interferon-alpha failure. This compound can be prepared by a four step sequence from a condensation of the 1-(3-pyridyl)ethanone with dimethyl formamide dimethylacetal, followed by successive cyclization with the methyl-nitrophenyl guanidine, hydrogenolysis and condensation with the benzoyl chloride of the methylpiperazine. Imatinib is the first of a new class of anticancer drugs that are specifically designed to target the molecular pathways involved (oncogenic event) in the development of disease. The Brc-Abl oncoprotein is a constitutively active tyrosine kinase that causes CML. Imatinib is a competitive inhibitor of this tyrosine kinase as well as Abl, Kit and the PDGFR kinases It binds to the ATP-binding site of the target kinase and prevents the transfer of phosphate from ATP to the tyrosine residues of various substrates and consequently blocks the proliferation of the leukemic cells. Phase II studies demonstrated that in chronic phase CML, over 90% of the patients had their leukocyte counts return to normal and 56% had a major cytogenic response. No phase III data is currently available. It is clear from the evidence available that imatinib has advantages over IFN-alpha, such as reduced toxicity, more rapid hematological response, higher rate of cytogenic response and oral administration. The drug is well tolerated, producing few side effects, classified as grade 1 nausea, muscle cramps, diarrhea, edema and vomiting. Imatinib is metabolized primarily by the CYP3A4 enzyme system and drugs capable of modulating this system would be expected to modify the patient's exposure. Novartis expects to launch imatinib for the treatment of gastrointestinal stromal tumors in 2002.

Chemical Properties

Off-White Solid

Originator

Novartis (Switzerland)

Uses

Imatinib Mesylate (STI571) is an orally bioavailability mesylate salt of Imatinib, which is a multi-target inhibitor of v-Abl, c-Kit and PDGFR with IC50 of 0.6 μM, 0.1 μM and 0.1 μM, respectively.

Uses

Imatinib Mesylate is orally bioavailability mesylate salt of Imatinib, which is a multi-target inhibitor of v-Abl, c-Kit and PDGFR with IC50 of 0.6 μM, 0.1 μM and 0.1 μM, respectively. Imatinib also known as Gleevec, Glivec, CGP-57148B, STI-571 & Imatinib

Uses

A tyrosine kinase inhibitor. Highly specific for BCR-ABL, the enzyme associated with chronic myelogenous leukemia (CML) and certain forms of acute lymphoblastic leukemia (ALL)

Uses

echinocandin antifungal, active against infections with Aspergillus and Candida, inhibits cell wall synthesis

Definition

ChEBI: A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.

brand name

Gleevec, Glivec

General Description

Imatinib is available in 100- and 400-mg capsules for oraladministration and is indicated for the treatment of CML,gastrointestinal stromal tumors (GIST) that express Kit andacute lymphoplastic leukemia that is positive for thePhiladelphia chromosome.
Bioavailability of the agent is nearly 100% by the oralroute. The agent is highly protein bound and metabolized tothe N-desmethyl derivative by CYP3A4-mediated removalof the piperazinyl methyl group. The resulting metabolite issimilar to the parent in activity. Elimination occurs primarilyin the feces, and the terminal half-life is 18 hours forthe parent and 40 hours of the N-desmethyl metabolite.Resistant forms of the TK are known, which have alteredamino acids that prevent binding. In addition, there may beincreased levels of the kinase itself. The drug is also a substratefor Pgp and an additional efflux transporter known asbreast cancer resistance protein (BCRP), both of which removethe drug from the cell. These transporters are also inhibitedby the agent as well. Severe side effects include ascites,neutropenia, thrombocytopenia, skin rash, andpulmonary edema. Less serious side effects include nausea/vomiting, heartburn, and headache but overall, the agentis better tolerated than most other medications used in treatingthe disease.

Biochem/physiol Actions

Imatinib mesylate is a tyrosine kinase inhibitor with antineoplastic activity. Imatinib is a potent inhibitor of the Bcr-Abl kinase encoded by the bcr-abl oncogene as well as receptor tyrosine kinases encoded by c-kit and platelet-derived growth factor receptor (PDGFR) oncogenes. Imatinib mesylate inhibition of Bcr-Abl tyrosine kinase created by the Philadelphia chromosome abnormality found in CML decreases proliferation and enhances apoptosis in leukemias CML and ALL. Inhibition of c-kit tyrosine activity inhibits mast-cell and cellular proliferation in those diseases overexpressing c-kit such as gastrointestinal stromal tumor (GIST).

storage

+4°C

References

1) Buchdunger, et al.(1996) Inhibition of the Abl Protein-Tyrosine Kinase in Vitro and in Vivo by a 2-Phenylpyrimidine Derivative; Cancer Res. 56 100 2) Heinrich et al (2000) Inhibition of c-kit receptor tyrosine kinase activity by STI 571, a selective tyrosine kinase inhibitor. Blood 96 925 3) Morioka et al. (2016) Effect of Collagen Type 1 or Human Fibronectin on Imatinib Cytotoxicity in Oral Squamous Cell Carcinoma; Pharmacology and Pharmacy, 7 255 [Focus Biomolecules Citation] 4) Hazekawa et al. (2017) Assessment of cytotoxicity of imatinib for oral squamous cell carcinoma by a real-time cell analysis system; E. J. Bio., 13 56 [ Focus Biomolecules Citation]

Imatinib mesylate Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 754)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+86-13288715578 +86-13231137666 sales@hbmojin.com China 12409 58
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118 xie@china-sinoway.com China 998 58
shandong perfect biotechnology co.ltd
+86-53169958659; +8618596095638 sales@sdperfect.com China 294 58
Henan Bao Enluo International TradeCo.,LTD
+86-17331933971 +86-17331933971 deasea125996@gmail.com China 2504 58
Nanjing Fred Technology Co., Ltd
+86-25-84696168 +86-15380713688 Austin@fredbio.com China 2449 58
Frapp's ChemicalNFTZ Co., Ltd.
+86 (576) 8169-6106 sales@frappschem.com China 885 50
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21703 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555 +8617317452075 jack.li@time-chemicals.com China 1807 55

Related articles

View Lastest Price from Imatinib mesylate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Imatinib Mesylate pictures 2024-03-19 Imatinib Mesylate
220127-57-1
US $650.00-350.00 / KG 1KG High Density 20 tons Sinoway Industrial co., ltd.
 Imatinib Mesylate (STI571) pictures 2024-03-12 Imatinib Mesylate (STI571)
220127-57-1
US $0.00 / g 1g 98% HPLC 1kg shandong perfect biotechnology co.ltd
Imatinib mesylate pictures 2023-12-06 Imatinib mesylate
220127-57-1
US $0.00-0.00 / kg 1kg 99.9%(HPLC) 10 tons Nanjing Fred Technology Co., Ltd
  • Imatinib Mesylate pictures
  • Imatinib Mesylate
    220127-57-1
  • US $650.00-350.00 / KG
  • High Density
  • Sinoway Industrial co., ltd.
  • Imatinib mesylate pictures
  • Imatinib mesylate
    220127-57-1
  • US $0.00-0.00 / kg
  • 99.9%(HPLC)
  • Nanjing Fred Technology Co., Ltd

Imatinib mesylate Spectrum

4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[[4-(3-pyridyl)pyrimidin-2-yl]amino]phenyl]benzamide Imatinib mesylate / 4-[(4-Methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide methanesulfonate Gleevec (Imatinib) IMatinib Mesylate(STI-571) Gleevec, Glivec, CGP-57148B, STI-571 4-[(4-Methyl-1-piperazinyl)Methyl]-N-[4-Methyl-3-[[4-(3-pyridinyl)-2-pyriMidinyl]aMino]phenyl]benzaMide Methanesulfonate IMATINIB METHANESULFONATE CGP-57148B 4-[(4-methylpiperazin-1-yl)methyl]-n-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide methanesulfonate Gleevac Gleevec (IMatinib Mesylate) CGP54148B CGP54148B; STI571; GLEEVEC;GLIVEC 4-(4-Methylpiperazin-1-ylMethyl)-N-[4-Methyl-3-(4-pyridin-3-yl-pyriMidin-2-ylaMino)phenyl]benzaMide Methanesulfonic acid salt Imantinib mesylate N-(4-Methyl-3-((4-(pyridin-3-yl)pyriMidin-2-yl)aMino)phenyl)-4-(4-Methylpiperazin-1-yl)benzaMide Methanesulfonate tinib Mesylate 4-[(4-methyl-1-piperazinyl)methyl]-n-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide monomethanesulfonate STI-571 IMATINIB BASE(IMA-3) ImatinibMesylate/Gleevec Imatinib Methanesulfonate, STI-571, CGP-57148B, Glivec, IMATINIB MESYLATE (IMATINIB METHANESULFONATE) alpha-IMATINIB MESYLATE Imatinib mesylate(TINIBS ) Imatinib mesylate Imatinib Methanesulphonate Salt N-(4-Methyl-3-((4-(pyridin-3-yl)pyriMidin-2-yl)aMino)phenyl)-4-((4-Methylpiperazin-1-yl)Methyl)benzaMide Methanesulfonate N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide methanesulfonic acid ST-1571 Mesylate Imatinib mesylate 4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide monomethanesulfonate 4-[(4-Methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide mesylate CGP 57148 Genfatinib Imatinib mesylate, >=99% 4-(4-methylpiperazinomethyl)benzoyl chloride dihydrochloride 4-(4-Methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]benz Bcr-abl Inhibitor IV, Imatinib GLIVEC; CGP-57148B; STI-571 Imatinib mesylate (Gleevec, Glivec, CGP-57148B, STI-571) Imatinib for system suitability Bcr-abl Inhibitor IV, Imatinib - CAS 220127-57-1 - Calbiochem Imatinib for system suitability CRS Imatinib mesilate CRS Imatinib mesylate salt ImatinibMesylate> Imatinib Mesylate β form Imatinib mesyL Imatinib mesylate(API) Imatinib mesylate USP/EP/BP PIRARUBICIN /CAS-220127-57-1 Imatinib mesilate (Y0001691) Imatinib MesylateQ: What is Imatinib Mesylate Q: What is the CAS Number of Imatinib Mesylate Q: What is the storage condition of Imatinib Mesylate Q: What are the applications of Imatinib Mesylate Imatinib for system suitability (Y0001692) 4-[(4-methyl-1-piperazinyl)methyl]-n-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide monomethanesulfonate Imatinib mesylate(alpha Form) Imatinib (STI-571) Mesylate Imatinib Mesylate 220127-57-1