Imatinib free base
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MedKoo CAT#: 100956

CAS#: 152459-95-5 (free base)

Description: Imatinib is 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. Imatinib was approved for medical use in the United States in 2001.


Price and Availability

Size
Price

1g
USD 150
10g
USD 750
Size
Price

2g
USD 250
20g
USD 1250
Size
Price

5g
USD 450
50g
USD 1950

Imatinib free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100956
Name: Imatinib free base
CAS#: 152459-95-5 (free base)
Chemical Formula: C29H31N7O
Exact Mass: 493.259
Molecular Weight: 493.615
Elemental Analysis: C, 70.56; H, 6.33; N, 19.86; O, 3.24


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; 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

InChi Key: KTUFNOKKBVMGRW-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H31N7O/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/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)

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


Technical Data

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

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

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

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

Inhibition of the bcr-abl TK results in decreased proliferation and enhanced apoptosis in malignant cells of Philadelphia-positive (Ph ) hematological malignancies such as CML and ALL; effects on c-kit TK activity inhibit mast-cell and cellular proliferation in those diseases overexpressing c-kit, such as mastocytosis and gastrointestinal stromal tumor (GIST). It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.


References

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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.

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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.

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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.

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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.

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