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MedKoo Cat#: 574745 | Name: Imatinib hydrochloride

Description:

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

Imatinib hydrochloride is a tyrosine kinase inhibitor.

Chemical Structure

Imatinib hydrochloride
Imatinib hydrochloride
CAS#862366-25-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 574745

Name: Imatinib hydrochloride

CAS#: 862366-25-4 (HCl)

Chemical Formula: C29H34ClN7O

Exact Mass: 0.0000

Molecular Weight: 532.09

Elemental Analysis: C, 65.46; H, 6.44; Cl, 6.66; N, 18.43; O, 3.01

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Related CAS #
220127-57-1 (mesylate) 152459-95-5 (free base) 862366-25-4 (HCl)
Synonym
Imatinib hydrochloride; Imatinib HCl; STI-571 hydrochloride
IUPAC/Chemical Name
N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)cyclohexa-1,5-dien-1-yl)-4-((4-methylpiperazin-1-yl)methyl)benzamide hydrochloride
InChi Key
DATHJYNMMUJECU-UHFFFAOYSA-N
InChi Code
InChI=1S/C29H33N7O.ClH/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;/h3-13,18-19,21,27H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34);1H
SMILES Code
CC1C=CC(=CC1NC2=NC=CC(=N2)C3=CN=CC=C3)NC(=O)C4=CC=C(C=C4)CN5CCN(CC5)C.Cl
Appearance
Solid 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
>3 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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Imatinib hydrochloride is a tyrosine kinase inhibitor.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 532.09 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.
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.