Imatinib mesylate
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100470

CAS#: 220127-57-1 (mesylate)

Description: Imatinib mesylate is the mesylate salt of imatinib, a tyrosine kinase inhibitor with antineoplastic activity. Imatinib binds to an intracellular pocket located within tyrosine kinases (TK), thereby inhibiting ATP binding and preventing phosphorylation and the subsequent activation of growth receptors and their downstream signal transduction pathways. This agent inhibits TK encoded by the bcr-abl oncogene as well as receptor TKs encoded by the c-kit and platelet-derived growth factor receptor (PDGFR) oncogenes. (last updated: 9/20/2016)


Price and Availability

Size
Price

1g
USD 150
10g
USD 550
100g
USD 1850
1kg
USD 4950
Size
Price

2g
USD 250
20g
USD 650
200g
USD 2650
Size
Price

5g
USD 450
50g
USD 950
500g
USD 3650

Imatinib mesylate, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 100470
Name: Imatinib mesylate
CAS#: 220127-57-1 (mesylate)
Chemical Formula: C30H35N7O4S
Exact Mass:
Molecular Weight: 589.71
Elemental Analysis: C, 61.10; H, 5.98; N, 16.63; O, 10.85; S, 5.44


Related CAS #: 220127-57-1 (mesylate)   152459-95-5 (free base)    

Synonym: CGP 57148; CGP57148; CGP-57148; CGP57148B; CGP-57148B; CGP 57148B; STI571; STI-571; STI 571; Imatinib mesylate; US brand name: Gleevec. Foreign brand name: Glivec

IUPAC/Chemical Name: N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide methanesulfonate

InChi Key: YLMAHDNUQAMNNX-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NC1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1)C4=CC=C(CN5CCN(C)CC5)C=C4.CS(=O)(O)=O


Technical Data

Appearance:
white to off-white to brownish or yellowish tinged crystalline powder.

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO at 100 mg/mL; very poorly soluble in ethanol; soluble in water at 200 mg/mL.

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

According to http://en.wikipedia.org/wiki/Imatinib, Imatinib was developed in the late 1990s by biochemist Nicholas Lydon, a former researcher for Novartis, oncologist Brian Druker of Oregon Health and Science University (OHSU), and Charles Sawyers of Memorial Sloan-Kettering Cancer Center, who led the clinical trials confirming its efficacy in CML. Important contributions to its development were also made by Carlo Gambacorti-Passerini, a physician scientist at University of Milano Bicocca in Italy, and John Goldman, a hematologist at Hammersmith Hospital in London, UK. Imatinib was developed by rational drug design. After the Philadelphia chromosome mutation and defective bcr-abl protein were discovered, the investigators screened chemical libraries to find a drug that would inhibit that protein. With high-throughput screening, they identified 2-phenylaminopyrimidine. This lead compound was then tested and modified by the introduction of methyl and benzamide groups to give it enhanced binding properties, resulting in imatinib  Gleevec received FDA approval in May 2001. On the same month it made the cover of TIME magazine as the "magic bullet" to cure cancer. Druker, Lydon and Sawyers received the Lasker-DeBakey Clinical Medical Research Award in 2009 for "converting a fatal cancer into a manageable chronic condition".
 
Imatinib is a small molecule kinase inhibitor. Gleevec film-coated tablets contain imatinib mesylate equivalent to 100 mg or 400 mg of imatinib free base. Imatinib mesylate is a white to off-white to brownish or yellowish tinged crystalline powder. Its molecular formula is C29H31N7O •CH4SO3 and its molecular weight is 589.7. Imatinib mesylate is soluble in aqueous buffers ≤ pH 5.5 but is very slightly soluble to insoluble in neutral/alkaline aqueous buffers. In non-aqueous solvents, the drug substance is freely soluble to very slightly soluble in dimethyl sulfoxide, methanol and ethanol, but is insoluble in n-octanol, acetone and acetonitrile. Inactive Ingredients: colloidal silicon dioxide (NF); crospovidone (NF); hydroxypropyl methylcellulose (USP); magnesium stearate (NF); and microcrystalline cellulose (NF). Tablet coating: ferric oxide, red (NF); ferric oxide, yellow (NF); hydroxypropyl methylcellulose (USP); polyethylene glycol (NF) and talc (USP).
 
Mechanism of Action
Imatinib mesylate is a protein-tyrosine kinase inhibitor that inhibits the bcr-abl tyrosine kinase, the constitutive abnormal tyrosine kinase created by the Philadelphia chromosome abnormality in CML. Imatinib inhibits proliferation and induces apoptosis in bcr-abl positive cell lines as well as fresh leukemic cells from Philadelphia chromosome positive chronic myeloid leukemia. Imatinib inhibits colony formation in assays using ex vivo peripheral blood and bone marrow samples from CML patients. In vivo, imatinib inhibits tumor growth of bcr-abl transfected murine myeloid cells as well as bcr-abl positive leukemia lines derived from CML patients in blast crisis.  Imatinib is also an inhibitor of the receptor tyrosine kinases for platelet-derived growth factor (PDGF) and stem cell factor (SCF), c-kit, and inhibits PDGF- and SCF-mediated cellular events. In vitro, imatinib inhibits proliferation and induces apoptosis in GIST cells, which express an activating c-kit mutation.
 
 


References

1: Hughes A, Yong ASM. Immune Effector Recovery in Chronic Myeloid Leukemia and Treatment-Free Remission. Front Immunol. 2017 Apr 24;8:469. doi: 10.3389/fimmu.2017.00469. eCollection 2017. Review. PubMed PMID: 28484463; PubMed Central PMCID: PMC5402174.

2: Nakamura K, Matsubara H, Akagi S, Sarashina T, Ejiri K, Kawakita N, Yoshida M, Miyoshi T, Watanabe A, Nishii N, Ito H. Nanoparticle-Mediated Drug Delivery System for Pulmonary Arterial Hypertension. J Clin Med. 2017 Apr 29;6(5). pii: E48. doi: 10.3390/jcm6050048. Review. PubMed PMID: 28468233.

3: Kayastha GK, Ranjitkar N, Gurung R, Kc RK, Karki S, Shrestha R, Rajbhandari P, Thapa RK, Poudyal B, Acharya P, Roberts DJ, Hayes B, Zimmerman M, Basnyat B. The use of Imatinib resistance mutation analysis to direct therapy in Philadelphia chromosome/BCR-ABL1 positive chronic myeloid leukaemia patients failing Imatinib treatment, in Patan Hospital, Nepal. Br J Haematol. 2017 May 3. doi: 10.1111/bjh.14683. [Epub ahead of print] Review. PubMed PMID: 28467002.

4: Lanke G, Lee JH. How best to manage gastrointestinal stromal tumor. World J Clin Oncol. 2017 Apr 10;8(2):135-144. doi: 10.5306/wjco.v8.i2.135. Review. PubMed PMID: 28439494; PubMed Central PMCID: PMC5385434.

5: Somlyai G, Collins TQ, Meuillet EJ, Hitendra P, D'Agostino DP, Boros LG. Structural homologies between phenformin, lipitor and gleevec aim the same metabolic oncotarget in leukemia and melanoma. Oncotarget. 2017 Mar 15. doi: 10.18632/oncotarget.16238. [Epub ahead of print] Review. PubMed PMID: 28418852.

6: Campiotti L, Suter MB, Guasti L, Piazza R, Gambacorti-Passerini C, Grandi AM, Squizzato A. Imatinib discontinuation in chronic myeloid leukaemia patients with undetectable BCR-ABL transcript level: A systematic review and a meta-analysis. Eur J Cancer. 2017 May;77:48-56. doi: 10.1016/j.ejca.2017.02.028. Epub 2017 Mar 30. Review. PubMed PMID: 28365527.

7: Poveda A, García Del Muro X, López-Guerrero JA, Cubedo R, Martínez V, Romero I, Serrano C, Valverde C, Martín-Broto J; GEIS (Grupo Español de Investigación en Sarcomas/Spanish Group for Sarcoma Research).. GEIS guidelines for gastrointestinal sarcomas (GIST). Cancer Treat Rev. 2017 Apr;55:107-119. doi: 10.1016/j.ctrv.2016.11.011. Epub 2017 Mar 2. Review. PubMed PMID: 28351781.

8: Alikian M, Gale RP, Apperley JF, Foroni L. Molecular techniques for the personalised management of patients with chronic myeloid leukaemia. Biomol Detect Quantif. 2017 Feb 14;11:4-20. doi: 10.1016/j.bdq.2017.01.001. eCollection 2017 Mar. Review. PubMed PMID: 28331814; PubMed Central PMCID: PMC5348117.

9: Keung EZ, Raut CP. Management of Gastrointestinal Stromal Tumors. Surg Clin North Am. 2017 Apr;97(2):437-452. doi: 10.1016/j.suc.2016.12.001. Review. PubMed PMID: 28325196.

10: Damrongwatanasuk R, Fradley MG. Cardiovascular Complications of Targeted Therapies for Chronic Myeloid Leukemia. Curr Treat Options Cardiovasc Med. 2017 Apr;19(4):24. doi: 10.1007/s11936-017-0524-8. Review. PubMed PMID: 28316033.

11: Das L, Gitlin M, Siegartel LR, Makenbaeva D. The value of open access and a patient centric approach to oral oncolytic utilization in the treatment of Chronic Myelogenous Leukemia: A U.S. perspective. Expert Rev Pharmacoecon Outcomes Res. 2017 Apr;17(2):133-140. doi: 10.1080/14737167.2017.1305892. Epub 2017 Mar 22. Review. PubMed PMID: 28287008.

12: Sankhala KK. Clinical development landscape in GIST: from novel agents that target accessory pathways to revisiting non-targeted therapies. Expert Opin Investig Drugs. 2017 Apr;26(4):427-443. doi: 10.1080/13543784.2017.1303045. Epub 2017 Mar 20. Review. PubMed PMID: 28267385.

13: Ramachandran KC, Narayanan G, Nair SG, Thambi SM, Kamala LH, Gopinath P, Sreedharan H. Isodicentric Philadelphia Chromosome: A Rare Chromosomal Aberration in Imatinib-Resistant Chronic Myelogenous Leukemia Patients - Case Report with Review of the Literature. Cytogenet Genome Res. 2016;150(3-4):273-280. doi: 10.1159/000458164. Epub 2017 Mar 3. Review. PubMed PMID: 28253493.

14: Saini L, Brandwein J. New Treatment Strategies for Philadelphia Chromosome-Positive Acute Lymphoblastic Leukemia. Curr Hematol Malig Rep. 2017 Apr;12(2):136-142. doi: 10.1007/s11899-017-0372-3. Review. PubMed PMID: 28243848.

15: Vigarios E, Epstein JB, Sibaud V. Oral mucosal changes induced by anticancer targeted therapies and immune checkpoint inhibitors. Support Care Cancer. 2017 May;25(5):1713-1739. doi: 10.1007/s00520-017-3629-4. Epub 2017 Feb 22. Review. PubMed PMID: 28224235.

16: Andrei M, Bandarchuk A, Abdelmalek C, Kundra A, Gotlieb V, Wang JC. PDGFRᵝ-Rearranged Myeloid Neoplasm with Marked Eosinophilia in a 37-Year-Old Man; And a Literature Review. Am J Case Rep. 2017 Feb 17;18:173-180. Review. PubMed PMID: 28209946; PubMed Central PMCID: PMC5325042.

17: Pasic I, Lipton JH. Current approach to the treatment of chronic myeloid leukaemia. Leuk Res. 2017 Apr;55:65-78. doi: 10.1016/j.leukres.2017.01.005. Epub 2017 Jan 11. Review. PubMed PMID: 28135648.

18: Tirumani SH, Baheti AD, Tirumani H, O'Neill A, Jagannathan JP. Update on Gastrointestinal Stromal Tumors for Radiologists. Korean J Radiol. 2017 Jan-Feb;18(1):84-93. doi: 10.3348/kjr.2017.18.1.84. Epub 2017 Jan 5. Review. PubMed PMID: 28096720; PubMed Central PMCID: PMC5240484.

19: Keating GM. Dasatinib: A Review in Chronic Myeloid Leukaemia and Ph+ Acute Lymphoblastic Leukaemia. Drugs. 2017 Jan;77(1):85-96. doi: 10.1007/s40265-016-0677-x. Review. PubMed PMID: 28032244.

20: Reiter A, Gotlib J. Myeloid neoplasms with eosinophilia. Blood. 2017 Feb 9;129(6):704-714. doi: 10.1182/blood-2016-10-695973. Epub 2016 Dec 27. Review. PubMed PMID: 28028030.