a small-molecule inhibitor
ChemicalBook > CAS DataBase List > Imatinib mesylate

Imatinib mesylate

a small-molecule inhibitor
Product Name
Imatinib mesylate
CAS No.
220127-57-1
Chemical Name
Imatinib mesylate
Synonyms
GLEEVEC;GLIVEC;Imatinib (Glivec);STI-571;Gleevac;CGP 57148;CGP54148B;Genfatinib;CGP-57148B;tinib Mesylate
CBNumber
CB7173646
Molecular Formula
C30H35N7O4S
Formula Weight
589.71
MOL File
220127-57-1.mol
More
Less

Imatinib mesylate Property

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.
InChI
InChI=1S/C29H31N7O.CH4O3S/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36;1-5(2,3)4/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34);1H3,(H,2,3,4)
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)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
CV5520550
HS Code 
29350090
Hazardous Substances Data
220127-57-1(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

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

Imatinib mesylate Chemical Properties,Usage,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

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

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

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

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

More
Less

Imatinib mesylate Suppliers

AnHui HaiKang Pharmaceutical Co., Ltd.
Tel
0556-5800026 17709662922
Email
melrose@worldpharma.cn
Country
China
ProdList
221
Advantage
55
Nanjing Yunzhi Xinhe Biotechnology Co., Ltd
Tel
19852363252; 19852363252
Email
2634809846@qq.com
Country
China
ProdList
53
Advantage
58
Jiangsu Xinglin Pharmaceutical Co., Ltd
Tel
18036652731
Email
2843986978@qq.com
Country
China
ProdList
54
Advantage
58
SiChuang NanBu Honesty Technology Co., Ltd.
Tel
0838-5675166 15883665058
Fax
0838-5675535
Email
nbcxkj@126.com
Country
China
ProdList
668
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3572
Advantage
66
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2338
Advantage
56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
More
Less

View Lastest Price from Imatinib mesylate manufacturers

Sinoway Industrial co., ltd.
Product
Imatinib Mesylate 220127-57-1
Price
US $650.00-350.00/KG
Min. Order
1KG
Purity
High Density
Supply Ability
20 tons
Release date
2023-11-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Imatinib mesylate 220127-57-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%-102% HPLC
Supply Ability
500KGS
Release date
2021-07-05
Nanjing Fred Technology Co., Ltd
Product
Imatinib mesylate 220127-57-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.9%(HPLC)
Supply Ability
10 tons
Release date
2023-12-06

220127-57-1, Imatinib mesylateRelated Search:


  • 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
  • Imatinib mesylate(alpha Form)
  • Imatinib (STI-571) Mesylate
  • Imatinib Mesylate 220127-57-1
  • IMATINIB MESYLATE (STI571 MESYLATE)
  • Imatinib mesylate - CGP 57148B | STI 571 | Gleevec
  • GLIVEC; CGP-57148B; STI-571
  • 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
  • GLIVEC
  • GLEEVEC
  • 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
  • Imatinib mesylate (Gleevec, Glivec, CGP-57148B, STI-571)
  • Imatinib for system suitability
  • Bcr-abl Inhibitor IV, Imatinib - CAS 220127-57-1 - Calbiochem
  • Imatinib (Glivec)
  • Imatinib for system suitability CRS
  • Imatinib mesilate CRS
  • Imatinib mesylate salt
  • ImatinibMesylate&gt
  • Imatinib Mesylate β form
  • Imatinib mesyL
  • Imatinib mesylate(API)
  • Imatinib mesylate USP/EP/BP