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.


Chemical Structure

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

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

Price and Availability

Size Price Availability Quantity
1.0g USD 150.0 Ready to ship
5.0g USD 250.0 Ready to ship
10.0g USD 400.0 Ready to ship
20.0g USD 650.0 Ready to ship
50.0g USD 1150.0 Ready to ship
100.0g USD 1850.0 Ready to ship
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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

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).

HS Tariff Code: 2934.99.9001

Biological target: Imatinib (STI571) is a tyrosine kinases inhibitor that selectively inhibits BCR/ABL, v-Abl, PDGFR and c-kit kinase activity.
In vitro activity: Furthermore, results showed that imatinib with the dose of 100 μg had the same effect as 25 μg amphotericin B on the viability of L. major promastigotes. In addition, imatinib with the dose of 100 μg had almost the same effect as 25 μg amphotericin B on the viability of L. major amastigotes [Table 1]. Three-way repeated ANOVA measurements showed that both two cyclic forms of parasites (P < 0.001), both different doses of imatinib (P < 0.001), and duration of exposure to imatinib (P < 0.001) were effective on survival percentage of parasite stages. As seen in Table 1, the average survival of amastigotes is significantly higher than promastigotes. Increasing the concentration of imatinib, the percentage of survival has declined, as well as with increasing exposure time, the parasite survival rate has decreased. As a result, it can be stated that the percentage of viability of promastigotes and amastigotes produced reverse ratio with the exposure time and drug dosage. For more investigation, the estimated marginal means for different groups and treatment type were presented in Table 2. Reference: Adv Biomed Res. 2019; 8: 61. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6839269/
In vivo activity: To translate findings in vivo, this study performed a time-resolved study assessing the effects of imatinib on macrophages and metabolic disease manifestations in HFD-induced obese mice: Reduction of TNFα in peritoneal and liver macrophages occurred most rapidly upon imatinib. Activated peritoneal macrophages are known to have both enhanced glycolysis and mitochondrial oxidation. Metabolic flux as another measure for macrophage activation confirmed altered polarization by lower metabolic oxidation upon imatinib. In the liver, this study was able to localize TNFα in liver macrophages, which decreased over time as shown by lower F4/80 area fraction and CD68 gene expression. Thus, it is conceivable that down-regulation of TNFα by imatinib interrupts the vicious cycle of resident liver macrophage activation and/or bone marrow-derived macrophage recruitment to the liver, subsequently lowering their activation and/or number. Reference: Sci Rep. 2018; 8: 15331. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6193017/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 74.0 149.91
Water 50.0 101.29

Preparing Stock Solutions

The following data is based on the product molecular weight 493.615 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Moslehi M, Namdar F, Esmaeilifallah M, Hejazi SH, Sokhanvari F, Siadat AH, Hosseini SM, Iraji F. Evaluation of Different Concentrations of Imatinib on the Viability of Leishmania major: An In Vitro Study. Adv Biomed Res. 2019 Oct 31;8:61. doi: 10.4103/abr.abr_58_19. PMID: 31737578; PMCID: PMC6839269. 2. Yao Z, Zhang J, Zhang B, Liang G, Chen X, Yao F, Xu X, Wu H, He Q, Ding L, Yang B. Imatinib prevents lung cancer metastasis by inhibiting M2-like polarization of macrophages. Pharmacol Res. 2018 Jul;133:121-131. doi: 10.1016/j.phrs.2018.05.002. Epub 2018 May 3. PMID: 29730267. 3. Tanaka A, Nishikawa H, Noguchi S, Sugiyama D, Morikawa H, Takeuchi Y, Ha D, Shigeta N, Kitawaki T, Maeda Y, Saito T, Shinohara Y, Kameoka Y, Iwaisako K, Monma F, Ohishi K, Karbach J, Jäger E, Sawada K, Katayama N, Takahashi N, Sakaguchi S. Tyrosine kinase inhibitor imatinib augments tumor immunity by depleting effector regulatory T cells. J Exp Med. 2020 Feb 3;217(2):e20191009. doi: 10.1084/jem.20191009. PMID: 31704808; PMCID: PMC7041710. 4. AlAsfoor S, Rohm TV, Bosch AJT, Dervos T, Calabrese D, Matter MS, Weber A, Cavelti-Weder C. Imatinib reduces non-alcoholic fatty liver disease in obese mice by targeting inflammatory and lipogenic pathways in macrophages and liver. Sci Rep. 2018 Oct 17;8(1):15331. doi: 10.1038/s41598-018-32853-w. PMID: 30333571; PMCID: PMC6193017.
In vitro protocol: 1. Moslehi M, Namdar F, Esmaeilifallah M, Hejazi SH, Sokhanvari F, Siadat AH, Hosseini SM, Iraji F. Evaluation of Different Concentrations of Imatinib on the Viability of Leishmania major: An In Vitro Study. Adv Biomed Res. 2019 Oct 31;8:61. doi: 10.4103/abr.abr_58_19. PMID: 31737578; PMCID: PMC6839269. 2. Yao Z, Zhang J, Zhang B, Liang G, Chen X, Yao F, Xu X, Wu H, He Q, Ding L, Yang B. Imatinib prevents lung cancer metastasis by inhibiting M2-like polarization of macrophages. Pharmacol Res. 2018 Jul;133:121-131. doi: 10.1016/j.phrs.2018.05.002. Epub 2018 May 3. PMID: 29730267.
In vivo protocol: 1. Tanaka A, Nishikawa H, Noguchi S, Sugiyama D, Morikawa H, Takeuchi Y, Ha D, Shigeta N, Kitawaki T, Maeda Y, Saito T, Shinohara Y, Kameoka Y, Iwaisako K, Monma F, Ohishi K, Karbach J, Jäger E, Sawada K, Katayama N, Takahashi N, Sakaguchi S. Tyrosine kinase inhibitor imatinib augments tumor immunity by depleting effector regulatory T cells. J Exp Med. 2020 Feb 3;217(2):e20191009. doi: 10.1084/jem.20191009. PMID: 31704808; PMCID: PMC7041710. 2. AlAsfoor S, Rohm TV, Bosch AJT, Dervos T, Calabrese D, Matter MS, Weber A, Cavelti-Weder C. Imatinib reduces non-alcoholic fatty liver disease in obese mice by targeting inflammatory and lipogenic pathways in macrophages and liver. Sci Rep. 2018 Oct 17;8(1):15331. doi: 10.1038/s41598-018-32853-w. PMID: 30333571; PMCID: PMC6193017.

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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.