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MedKoo Cat#: 100791 | Name: Sunitinib free base
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Description:

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

Sunitinib free base is an oral, small-molecule, multi-targeted receptor tyrosine kinase (RTK) inhibitor. Sunitinib malate salt was approved by the FDA for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST) on January 26, 2006. Sunitinib inhibits cellular signaling by targeting multiple receptor tyrosine kinases (RTKs). The simultaneous inhibition of these targets therefore reduces tumor vascularization and triggers cancer cell apoptosis and thus results in tumor shrinkage. Sunitinib also inhibits CD117 (c-KIT), the receptor tyrosine kinase that (when improperly activated by mutation) drives the majority of gastrointestinal stromal cell tumors.

Chemical Structure

Sunitinib free base
Sunitinib free base
CAS#557795-19-4 (free base)

Theoretical Analysis

MedKoo Cat#: 100791

Name: Sunitinib free base

CAS#: 557795-19-4 (free base)

Chemical Formula: C22H27FN4O2

Exact Mass: 398.2118

Molecular Weight: 398.48

Elemental Analysis: C, 66.31; H, 6.83; F, 4.77; N, 14.06; O, 8.03

Price and Availability

Size Price Availability Quantity
50mg USD 90.00 Ready to ship
100mg USD 150.00 Ready to ship
250mg USD 250.00 Ready to ship
500mg USD 350.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 650.00 Ready to ship
5g USD 1,250.00 Ready to ship
10g USD 2,050.00 Ready to ship
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Related CAS #
341031-54-7 (malate) 557795-19-4 (free base) 342641-94-5 1126641-10-8 (maleate) 1221149-36-5 (acetate) 1327155-72-5 (HCl) 1275588-72-1 (mesylate) 1332306-95-2 (oxalate)
Synonym
SU11248; SU-11248; SU 11248; SU011248; sunitinib. US brand name: Sutent.
IUPAC/Chemical Name
(Z)-N-(2-(diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
InChi Key
WINHZLLDWRZWRT-ATVHPVEESA-N
InChi Code
InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
SMILES Code
CCN(CC)CCNC(=O)C1=C(NC(=C1C)/C=C2/C3=C(C=CC(=C3)F)NC2=O)C
Appearance
Yellow 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, not in water
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
More Info
Biological target:
Sunitinib (SU 11248) is a tyrosine kinase inhibitor with IC50s of 80 nM and 2 nM for VEGFR2 and PDGFRβ, respectively.
In vitro activity:
In order to determine the impact of sunitinib on ectopic endometrial cells, ectopic and normal endometrial cells were treated with sunitinib at appointed concentrations of 0, 1, 2, 4, 8, and 16 uM for 48 hours. The MTT assay revealed that the half maximal inhibitory concentration (IC50) of normal endometrial cells to sunitinib (IC50 = 7.9 μM) was significantly higher, when compared to ectopic endometrial cells (IC50 = 3.32 μM), suggesting that sunitinib has no effect on the normal endometrium within the therapeutic concentration range, since it is on the ectopic endometrium in vitro (Figure 2A). Then, it was measured that sunitinib reduced the cell apoptosis by nuclear-fluorescence staining. These results show that the number of apoptotic cells in the ectopic endometrial group (100x) increased with the increase in sunitinib concentration (Figure 2B). Furthermore, in order to confirm the results above, the cell apoptosis was determined by flow cytometry. The cell apoptosis rate (FITC + plus FITC+/PI+) in ectopic endometrial cells was 51.9%±8.3% and 78.8% ± 3.2% at a sunitinib concentration of 4 μM and 8 μM, respectively, and both were significantly higher than that in normal endometrial cells, with 0.2% ± 1.2% (vs ectopic endometrial cells, P < .0001, t = 26.89) and 68.1% ± 2.1% (vs ectopic endometrial cells, P = .025, t = 3.49), respectively (Figure 2C). These results demonstrate that sunitinib can affect the cell proliferation and apoptosis of ectopic endometrial cells in a dose-dependent manner. Reference: J Clin Lab Anal. 2020 Nov;34(11):e23482. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7676178/
In vivo activity:
Mice were treated orally with sunitinib (7.5 mg/kg/day) for 2 weeks. Sunitinib did not affect body weight, but increased plasma ALT activity 6-fold. Protein and mRNA expression of several subunits of mitochondrial enzyme complexes were decreased in mitochondria from sunitinib-treated mice. Protein expression of PGC-1α, citrate synthase activity and mtDNA copy number were all decreased in livers of sunitinib-treated mice, indicating impaired mitochondrial proliferation. Caspase 3 activation and TUNEL-positive hepatocytes were increased in livers of sunitinib-treated mice, indicating hepatocyte apoptosis. In conclusion, sunitinib caused concentration-dependent toxicity in isolated mitochondria at concentrations reached in livers in vivo and inhibited hepatic mitochondrial proliferation. Daily mitochondrial insults and impaired mitochondrial proliferation most likely explain hepatocellular injury observed in mice treated with sunitinib. Reference: Toxicology. 2018 Nov 1;409:13-23. https://www.sciencedirect.com/science/article/abs/pii/S0300483X18301574?via%3Dihub
Solvent mg/mL mM
Solubility
DMSO 25.0 62.74
Ethanol 8.0 20.08
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 398.48 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. Li J, Abudula M, Fan X, Wang F, Chen Y, Liu L. Sunitinib induces primary ectopic endometrial cell apoptosis through up-regulation of STAT1 in vitro. J Clin Lab Anal. 2020 Nov;34(11):e23482. doi: 10.1002/jcla.23482. Epub 2020 Aug 5. PMID: 32761670; PMCID: PMC7676178. 2. Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. PMID: 12538485. 3. Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. PMID: 12538485. 4. Paech F, Abegg VF, Duthaler U, Terracciano L, Bouitbir J, Krähenbühl S. Sunitinib induces hepatocyte mitochondrial damage and apoptosis in mice. Toxicology. 2018 Nov 1;409:13-23. doi: 10.1016/j.tox.2018.07.009. Epub 2018 Jul 18. PMID: 30031043.
In vitro protocol:
1. Li J, Abudula M, Fan X, Wang F, Chen Y, Liu L. Sunitinib induces primary ectopic endometrial cell apoptosis through up-regulation of STAT1 in vitro. J Clin Lab Anal. 2020 Nov;34(11):e23482. doi: 10.1002/jcla.23482. Epub 2020 Aug 5. PMID: 32761670; PMCID: PMC7676178. 2. Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. PMID: 12538485.
In vivo protocol:
1. Mendel DB, Laird AD, Xin X, Louie SG, Christensen JG, Li G, Schreck RE, Abrams TJ, Ngai TJ, Lee LB, Murray LJ, Carver J, Chan E, Moss KG, Haznedar JO, Sukbuntherng J, Blake RA, Sun L, Tang C, Miller T, Shirazian S, McMahon G, Cherrington JM. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/pharmacodynamic relationship. Clin Cancer Res. 2003 Jan;9(1):327-37. PMID: 12538485. 2. Paech F, Abegg VF, Duthaler U, Terracciano L, Bouitbir J, Krähenbühl S. Sunitinib induces hepatocyte mitochondrial damage and apoptosis in mice. Toxicology. 2018 Nov 1;409:13-23. doi: 10.1016/j.tox.2018.07.009. Epub 2018 Jul 18. PMID: 30031043.
1: Pan M, Xu X, Zhang D, Cao W. Exploring the Immune Landscape of ccRCC: Prognostic Signatures and Therapeutic Implications. J Cell Mol Med. 2024 Nov;28(22):e70212. doi: 10.1111/jcmm.70212. PMID: 39557632. 2: Ghosh AK, Chen Y, Gadi RK, Sonawane A, Gamage SP, Tesmer JG. Design, synthesis, and X-ray structural studies of a series of highly potent, selective, and drug-like G protein-coupled receptor kinase 5 inhibitors. Eur J Med Chem. 2024 Nov 8;282:117024. doi: 10.1016/j.ejmech.2024.117024. Epub ahead of print. PMID: 39549325. 3: Tacelli M, Partelli S, Falconi M, Arcidiacono PG, Capurso G. Pancreatic Neuroendocrine Neoplasms: Classification and Novel Role of Endoscopic Ultrasound in Diagnosis and Treatment Personalization. United European Gastroenterol J. 2024 Nov 14. doi: 10.1002/ueg2.12710. Epub ahead of print. PMID: 39540703. 4: Palmerini E, Lopez Pousa A, Grignani G, Redondo A, Hindi N, Provenzano S, Sebio A, Lopez Martin JA, Valverde C, Martinez Trufero J, Gutierrez A, de Alava E, Gomez MPA, D'Ambrosio L, Collini P, Bazzocchi A, Moura DS, Ibrahim T, Stacchiotti S, Broto JM. Nivolumab and sunitinib in patients with advanced bone sarcomas: A multicenter, single-arm, phase 2 trial. Cancer. 2024 Nov 14. doi: 10.1002/cncr.35628. Epub ahead of print. PMID: 39540661. 5: Khaleel S, Perera M, Papa N, Kuo F, Golkaram M, Rappold P, Kotecha RR, Coleman J, Russo P, Motzer R, Reznik E, Hakimi AA. Gene expression of prostate- specific membrane antigen (FOLH1) in clear cell renal cell carcinoma predicts angiogenesis and response to tyrosine kinase inhibitors. Urol Oncol. 2024 Nov 12:S1078-1439(24)00694-X. doi: 10.1016/j.urolonc.2024.10.013. Epub ahead of print. PMID: 39537440. 6: Wang S, Zhang R, Wang S, Guo Q, Yin D, Song Y, She X, Wang X, Duan J. Osteonecrosis of the jaw in patients with clear cell renal cell carcinoma treated with targeted agents: a case series and large-scale pharmacovigilance analysis. Front Pharmacol. 2024 Oct 29;15:1309148. doi: 10.3389/fphar.2024.1309148. PMID: 39534085; PMCID: PMC11555396. 7: Pereira MM, Couto E, Shamseddine A, Macedo T. Two Decades of Gastrointestinal Stromal Tumor Management With First-Line Treatment: A Case Report. Cureus. 2024 Oct 12;16(10):e71299. doi: 10.7759/cureus.71299. PMID: 39529789; PMCID: PMC11552204. 8: Ara B, Babar A, Atif D, Ghafoor B, Shah M, Abdullah SM, Safi D, Kamran A. Systemic therapy for non-clear cell renal cell carcinomas: A systematic review. J Oncol Pharm Pract. 2024 Nov 11:10781552241289920. doi: 10.1177/10781552241289920. Epub ahead of print. PMID: 39529367. 9: Huang S, Qin X, Fu S, Hu J, Jiang Z, Hu M, Zhang B, Liu J, Chen Y, Wang M, Liu X, Chen Z, Wang L. STAMBPL1/TRIM21 Balances AXL Stability Impacting Mesenchymal Phenotype and Immune Response in KIRC. Adv Sci (Weinh). 2024 Nov 11:e2405083. doi: 10.1002/advs.202405083. Epub ahead of print. PMID: 39527690. 10: El Hafi M, Anouar EH, Lahmidi S, Boulhaoua M, Loubidi M, Alanazi AS, Filali I, Hefnawy M, El Ghayati L, Mague JT, Essassi EM. Synthesis of New Pyrazolo[3,4-d]pyrimidine Derivatives: NMR Spectroscopic Characterization, X-Ray, Hirshfeld Surface Analysis, DFT, Molecular Docking, and Antiproliferative Activity Investigations. Molecules. 2024 Oct 24;29(21):5020. doi: 10.3390/molecules29215020. PMID: 39519663; PMCID: PMC11547452. 11: Iyer KK, Poel D, Miggelenbrink A, Kerkhof W, Janssen J, Bakkerus L, de Jong L, van den Hombergh E, Nagtegaal ID, Tauriello DVF, van Erp NP, Verheul HMW. High-dose short-term osimertinib treatment is effective in patient-derived metastatic colorectal cancer organoids. BJC Rep. 2024 Apr 3;2(1):29. doi: 10.1038/s44276-024-00042-0. PMID: 39516561; PMCID: PMC11523998. 12: Haller V, Reiff C, Hamacher R, Kostbade K, Kaths M, Treckmann J, Bertram S, Zaun Y, Bauer S, Falkenhorst J. Overall survival of patients with KIT-mutant metastatic GIST in the era of multiple kinase inhibitor availability. J Cancer Res Clin Oncol. 2024 Nov 9;150(11):489. doi: 10.1007/s00432-024-05965-2. PMID: 39516299; PMCID: PMC11549121. 13: Hua Y, Qin M, Lu S, Zhang Y, Tan S, Ding D, Wang L. Hyaluronic acid- functionalized MOFs for combined sunitinib and siRNA therapy in renal cell carcinoma. Int J Biol Macromol. 2024 Nov 6;283(Pt 1):137317. doi: 10.1016/j.ijbiomac.2024.137317. Epub ahead of print. PMID: 39510472. 14: Joensuu H. Selection between sunitinib and ripretinib using mutation analysis for gastrointestinal stromal tumor patients progressing on imatinib. Transl Gastroenterol Hepatol. 2024 Sep 11;9:52. doi: 10.21037/tgh-24-32. PMID: 39503033; PMCID: PMC11535786. 15: Semenyuta I, Los O, Sinenko V, Zhirnov V, Potikha L, Kobzar O, Brovarets V. Design, Synthesis, and Antitumor Potential of New Thiazole--contained 5-Fluoro-2-Oxindole Derivatives as Sunitinib Analogues. Curr Med Chem. 2024 Nov 4. doi: 10.2174/0109298673346427241016100726. Epub ahead of print. PMID: 39501958. 16: Che X, Tian X, Wang Z, Zhu S, Ye S, Wang Y, Chen Y, Huang Y, Anwaier A, Yao P, Chen Y, Wu K, Liu Y, Xu W, Zhang H, Ye D. Systematic multiomics analysis and in vitro experiments suggest that ITGA5 could serve as a promising therapeutic target for ccRCC. Cancer Cell Int. 2024 Nov 5;24(1):363. doi: 10.1186/s12935-024-03546-4. PMID: 39501306; PMCID: PMC11539770. 17: Hu XC, Yu QY, Ding HP, Xiao F, Gu CY. Exploration on the construction of a bladder cancer prognostic model based on disulfidptosis-related lncRNAs and its clinical significance. Sci Rep. 2024 Nov 5;14(1):26751. doi: 10.1038/s41598-024-78481-5. PMID: 39500988; PMCID: PMC11538480. 18: Wu S, Zuo Y, Ye M, Wang K, Wang X, Yang X, Wang C. Co‑occurrence of clear cell renal cell carcinoma and bladder urothelial carcinoma: A case report and literature review. Oncol Lett. 2024 Oct 23;29(1):21. doi: 10.3892/ol.2024.14768. PMID: 39492932; PMCID: PMC11526436. 19: Zhang XL, Yue YX, Yang Y, Ying AK, Ma R, Chen J, Chen FY, Hou XY, Pan YC, Ren DZ, Yang T, Li ZQ, Guo DS. A single molecule carrier for ocular posterior segment diseases. J Control Release. 2024 Oct 26:S0168-3659(24)00725-9. doi: 10.1016/j.jconrel.2024.10.052. Epub ahead of print. PMID: 39490420. 20: Li Q, Zeng K, Chen Q, Han C, Wang X, Li B, Miao J, Zheng B, Liu J, Yuan X, Liu B. Atractylenolide I inhibits angiogenesis and reverses sunitinib resistance in clear cell renal cell carcinoma through ATP6V0D2-mediated autophagic degradation of EPAS1/HIF2α. Autophagy. 2024 Nov 4:1-20. doi: 10.1080/15548627.2024.2421699. Epub ahead of print. PMID: 39477683.