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Purity: ≥98%
Imatinib (formerly STI-571, trade name Gleevec and Glivec) is an orally bioavailable multi-targeted kinase inhibitor with potential anticancer activity. With IC50 values of 0.6 μM, 0.1 μM, and 0.1 μM in cell-free and/or cell-based assays, respectively, it inhibits v-Abl, c-Kit, and PDGFR. In order to inhibit ATP binding, phosphorylation, and the subsequent activation of growth receptors and their downstream signal transduction pathways, imatinib binds to the intracellular domain of tyrosine kinases (TK). Tyrosine kinases carried by the bcr-abl oncogene, along with receptor TKs carried by the c-kit and platelet-derived growth factor receptor (PDGFR) oncogenes, are inhibited by imatinib.
| Targets |
PDGFR (IC50 = 100 nM); c-Kit (IC50 = 100 nM); v-Abl (IC50 = 600 nM)
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| ln Vitro |
Imatinib (STI571) inhibits c-Kit autophosphorylation, MAPK activation, and Akt activation without changing the overall amounts of c-kit, MAPK, or Akt proteins. Approximately 100 nM is the concentration at which these effects are 50% inhibited[1].
Imatinib (STI571) has a very high in vitro IC50 of 25 nM against the kinase Bcr-Abl, which causes chronic myeloid leukemia. Additionally, Kit (in vitro IC50: 410 nM) and PDGFR (in vitro IC50: 380 nM) are effectively inhibited by imatinib[2]. Imatinib (STI571) is a multi-target inhibitor of v-Abl, c-Kit, and it also inhibits the native PDGFβ receptor, Bcr/Abl, v-Abl, Tel/Abl, and c-Kit. However, it does not inhibit the EGFR, c-Fms, Flt3, Src family kinases, or numerous other tyrosine kinases. Imatinib has no effect on untransformed Ba/F3 cells growing in IL-3 or on Ba/F3 cells transformed by Tel/JAK2[4]. However, it inhibits the tyrosine phosphorylation and cell growth of Ba/F3 cells expressing Bcr/Abl, Tel/Abl, Tel/PDGFβR, and Tel/Arg with an IC50 of approximately 0.5 μM in each case. Imatinib (STI571), a multi-target inhibitor, has IC50s of 32.4 and 32.8 μM for v-Abl, c-Kit, and BON-1 and H727 cells after 48 hours of exposure[6]. |
| ln Vivo |
Tumor growth inhibition is 59.437% in the phosphorothioate antisense oligodeoxynucleotides (PS-ASODN) group, significantly higher than in the liposome negative control group (2.759%) and the Imatinib (STI571) multi-target inhibitor of v-Abl, c-Kit and group (11.071%) groups. When compared to the Imatinib group (1.838±0.241), liposome negative control group (2.013±0.273), and saline group (2.004±0.163), telomerase activity is significantly lower (P<0.01) in the PS-ASODN group (0.689±0.158)[7].
Imatinib (25 mg/kg/day, p.o.) inhibits the growth of endometriotic tissue and decreases the quantity of ovarian follicles in a rat model. Through its inhibitory effects on angiogenesis and cell proliferation, imatinib effectively treats experimental endometriosis[8].
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| Enzyme Assay |
Rabbit antiserum is used to immunoprecipitate the PDGF receptor from extracts of BALB/c 3T3 cells, which is then left on ice for two hours. Antigen-antibody complexes are gathered using protein A-Sepharose beads. TNET (50 mM Tris, pH 7.5, 140 mM NaCl, 5 mM EDTA, 1% Triton X-100), TNE (50 mM Tris, pH 7.5, 140 mM EDTA), and kinase buffer (20 mM Tris, pH 7.5, 10 mM MgCl2) are the three solutions used to wash the immunoprecipitates twice. A variety of drug concentrations are added to the reaction mixture after PDGF (50 ng/mL) stimulation for 10 minutes at 4 °C. Incubation with 10 μCi [7-33P]-ATP and l μM ATP for 10 minutes at 4 °C is used to measure PDGF receptor kinase activity. SDS-PAGE is used to separate immune complexes on 7.5% gels.
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| Cell Assay |
In triplicate, BON-1 and NCI-H727 cells are seeded into flat-bottomed 96-well plates, and they are then left to adhere overnight in either RPMI 1640 complete medium or 10% fetal bovine serum-supplemented DMEM. The medium is then changed to either serum-free medium (which serves as a negative control) or serum-free medium that contains serial dilutions of imatinib. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay is used to count the number of metabolically active cells after 48 hours (control cultures do not reach confluence). The absorbance is then measured at 540 nm using a Packard Spectra microplate reader. Inhibition rate = (1 − a / b) × 100% is the formula used to calculate growth inhibition, where a and b represent the absorbance values of the treated and control groups, respectively.
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| Animal Protocol |
Mice: The 40 SCID mice with tumors are split into four groups at random, with 10 mice in each group: the PS-ASODN group (5 μM, intratumor injection once daily, 0.2 mL per mouse), the Imatinib group (0.1 mg/g body weight), the liposome negative control group (0.01 mL/g), and the saline group (0.01 mL/g). From the seventh to the twenty-eighth day following implantation, the mice in each group are given the appropriate treatment by intratumor injection once a day. The mice are killed after 28 days, and an electronic scale and a vernier caliper are used to measure the tumor's weight as well as its longest and shortest diameters. Tumor growth inhibition is computed.
Rats: It uses adult female Wistar-Albino rats weighing between 220 and 240 g. To assess if endometriosis has occurred, the rats have a second laparotomy twenty-one days following the first surgical procedure. Anastrozole (0.004 mg/day, p.o.), Imatinib (25 mg/kg/day), or normal saline (0.1 mL, i.p.) are the three groups of rats that are randomly assigned to receive treatment for 14 days after having visually confirmed endometriotic implants in 24 rats. |
| References |
| Molecular Formula |
C29H31N7O
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|---|---|
| Molecular Weight |
493.6
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| Exact Mass |
493.26
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| Elemental Analysis |
C, 70.56; H, 6.33; N, 19.86; O, 3.24
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| CAS # |
152459-95-5
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| Related CAS # |
Imatinib-d8;1092942-82-9;Imatinib-d4;1134803-16-9;Imatinib-d3 hydrochloride;1134803-18-1;Imatinib Mesylate;220127-57-1;N-Desmethyl imatinib;404844-02-6
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| Appearance |
white to off-white to brownish or yellowish tinged crystalline powder
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| SMILES |
CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5
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| InChi Key |
KTUFNOKKBVMGRW-UHFFFAOYSA-N
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| 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)
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| Chemical Name |
4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
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| Synonyms |
CGP-57148B; ST-1571, CGP057148B; CGP 57148; CGP57148; CGP-57148; CGP57148B; CGP 57148B; STI571; STI 571; Imatinib; US brand name: Gleevec; Foreign brand name: Glivec
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
2% DMSO+30% PEG 300+2% Tween 80+ddH2O: 2mg/mL (Please use freshly prepared in vivo formulations for optimal results.)
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0259 mL | 10.1297 mL | 20.2593 mL | |
| 5 mM | 0.4052 mL | 2.0259 mL | 4.0519 mL | |
| 10 mM | 0.2026 mL | 1.0130 mL | 2.0259 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05493215 | Active Recruiting |
Drug: Imatinib | Gastrointestinal Stromal Tumors | Reema A. Patel | November 2023 | Phase 2 |
| NCT04138381 | Active Recruiting |
Drug: Imatinib Drug: Selinexor |
GIST Drug Use |
Grupo Espanol de Investigacion en Sarcomas |
August 16, 2019 | Phase 1 Phase 2 |
| NCT01742299 | Active Recruiting |
Drug: imatinib mesylate | GIST and CML | Novartis Pharmaceuticals | March 26, 2013 | Phase 4 |
| NCT02413736 | Active Recruiting |
Drug: Imatinib | Sarcoma | Heikki Joensuu | May 2015 | Phase 3 |
| NCT03193281 | Active Recruiting |
Drug: Dasatinib Drug: Imatinib |
Chronic Myeloid Leukemia | University of Auckland, New Zealand |
July 17, 2017 | Phase 2 |
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