Imatinib free base
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.
For research use only. We do not sell to patients.
Chemical Information
| Name | Imatinib free base |
|---|---|
| Iupac Chemical Name | N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide |
| Synonyms | CGP 57148; CGP57148; CGP-57148; CGP57148B; CGP-57148B; CGP 57148B; STI571; STI-571; STI 571; Imatinib; US brand name: Gleevec. Foreign brand name: Glivec |
| Molecular Formula | C29H31N7O |
| Molecular Weight | 493.60 |
| Smile | O=C(NC1=CC=C(C)C(NC2=NC=CC(C3=CC=CN=C3)=N2)=C1)C4=CC=C(CN5CCN(C)CC5)C=C4 |
| InChiKey | KTUFNOKKBVMGRW-UHFFFAOYSA-N |
| InChi | 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) |
| CAS Number | 152459-95-5 (free base) |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
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| Mechanism | |
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| Clinical study |
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.
Chemical Structure
