Cabozantinib (free base)

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

Description:Cabozantinib, also known as XL-184 or BMS-907351, is an orally bioavailable, small molecule receptor tyrosine kinase (RTK) inhibitor with potential antineoplastic activity. Cabozantinib strongly binds to and inhibits several tyrosine receptor kinases. Specifically, cabozantinib appears to have a strong affinity for the hepatocyte growth factor receptor (Met) and vascular endothelial growth factor receptor 2 (VEGFR2), which may result in inhibition of tumor growth and angiogenesis, and tumor regression.Cabozantinib was approved by the U.S. FDA in November 2012 for the treatment of medullary thyroid cancer.

Price and Availability

Cabozantinib (XL184) (free base), purity > 98%, is in stock. The same day shipping out after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 200595Name: Cabozantinib (free base)CAS#: 849217-68-1 (free base)Chemical Formula: C28H24FN3O5Exact Mass: 501.17Molecular Weight: 501.51Elemental Analysis:C, 67.06; H, 4.82; F, 3.79; N, 8.38; O, 15.95

Related CAS #:1140909-48-3 (malate)849217-68-1 (free base)

Synonym:XL-184; XL184; XL 184; BMS 907351; BMS-907351; BMS907351; Cabozantinib, Cabozantinib free base; trade name Cometriq

IUPAC/Chemical Name:N-{4-[(6,7-dimethoxyquinolin-4-yl)oxy]phenyl}-N'-(4-fluorophenyl)cyclopropane-1,1- dicarboxamide

InChi Key:ONIQOQHATWINJY-UHFFFAOYSA-N

InChi Code:InChI=1S/C28H24FN3O5/c1-35-24-15-21-22(16-25(24)36-2)30-14-11-23(21)37-20-9-7-19(8-10-20)32-27(34)28(12-13-28)26(33)31-18-5-3-17(29)4-6-18/h3-11,14-16H,12-13H2,1-2H3,(H,31,33)(H,32,34)

SMILES Code:O=C(C1(C(NC2=CC=C(F)C=C2)=O)CC1)NC3=CC=C(OC4=CC=NC5=CC(OC)=C(OC)C=C45)C=C3

Technical Data

Additional Information

Related CAS#CAS#849217-68-1 (Cabozantinib free base); CAS#1140909-48-3 (Cabozantinib malate salt).

Cabozantinib (Marketed under the tradename Cometriq, formerly known as XL184) is a small molecule inhibitor of the tyrosine kinases c-Met and VEGFR2, and has been shown to reduce tumor growth, metastasis, and angiogenesis. It was developed by Exelixis Inc. Cabozantinib was granted orphan-drug status by the U.S. Food and Drug Administration (FDA) in January 2011. Cabozantinib was approved by the U.S. FDA in November 2012 for the treatment of medullary thyroid cancer[2] and it is currently undergoing clinical trials for the treatment of prostate, ovarian, brain, melanoma, breast, non-small cell lung, hepatocellular and kidney cancers. (source: http://en.wikipedia.org/wiki/Cabozantinib).        

References

1: Weitzman SP, Cabanillas ME. The treatment landscape in thyroid cancer: a focus on cabozantinib. Cancer Manag Res. 2015 Aug 19;7:265-78. doi: 10.2147/CMAR.S68373. eCollection 2015. Review. PubMed PMID: 26316818; PubMed Central PMCID: PMC4547654.

2: Zhang B, Zhang X, Zhou T, Liu J. Clinical observation of liver cancer patients treated with axitinib and cabozantinib after failed sorafenib treatment: a case report and literature review. Cancer Biol Ther. 2015;16(2):215-8. doi: 10.4161/15384047.2014.962318. Review. PubMed PMID: 25668362; PubMed Central PMCID: PMC4622678.

3: Fay AP, Albiges L, Bellmunt J. Current role of cabozantinib in metastatic castration-resistant prostate cancer. Expert Rev Anticancer Ther. 2015 Feb;15(2):151-6. doi: 10.1586/14737140.2015.1003047. Epub 2015 Jan 14. Review. PubMed PMID: 25586337.

4: Roy S, Narang BK, Rastogi SK, Rawal RK. A novel multiple tyrosine-kinase targeted agent to explore the future perspectives of anti-angiogenic therapy forthe treatment of multiple solid tumors: cabozantinib. Anticancer Agents Med Chem. 2015;15(1):37-47. Review. PubMed PMID: 25181996.

5: Hoy SM. Cabozantinib: a review of its use in patients with medullary thyroid cancer. Drugs. 2014 Aug;74(12):1435-44. doi: 10.1007/s40265-014-0265-x. Review. PubMed PMID: 25056653.

6: Nix NM, Braun K. Cabozantinib for the treatment of metastatic medullary thyroid carcinoma. J Adv Pract Oncol. 2014 Jan;5(1):47-50. Review. PubMed PMID: 25032033; PubMed Central PMCID: PMC4093460.

7: Colombo JR, Wein RO. Cabozantinib for progressive metastatic medullary thyroid cancer: a review. Ther Clin Risk Manag. 2014 May 28;10:395-404. doi: 10.2147/TCRM.S46041. eCollection 2014. Review. PubMed PMID: 24920914; PubMed Central PMCID: PMC4043815.

8: Vaishampayan UN. Development of cabozantinib for the treatment of prostate cancer. Core Evid. 2014 Apr 23;9:61-7. doi: 10.2147/CE.S48498. eCollection 2014.Review. Erratum in: Core Evid. 2014;9:69. PubMed PMID: 24790591; PubMed Central PMCID: PMC4003147.

9: Grüllich C. Cabozantinib: a MET, RET, and VEGFR2 tyrosine kinase inhibitor. Recent Results Cancer Res. 2014;201:207-14. doi: 10.1007/978-3-642-54490-3_12. Review. PubMed PMID: 24756794.

10: Pinto A. Cabozantinib: a novel agent with a dual mechanism of action for castration-resistant prostate carcinoma. Cancer Chemother Pharmacol. 2014 Feb;73(2):219-22. doi: 10.1007/s00280-013-2343-2. Epub 2013 Nov 8. Review. PubMed PMID: 24202668.

11: Karras S, Pontikides N, Krassas GE. Pharmacokinetic evaluation of cabozantinib for the treatment of thyroid cancer. Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):507-15. doi: 10.1517/17425255.2013.780028. Review. PubMed PMID: 23488614.

12: Nagilla M, Brown RL, Cohen EE. Cabozantinib for the treatment of advanced medullary thyroid cancer. Adv Ther. 2012 Nov;29(11):925-34. doi: 10.1007/s12325-012-0060-6. Epub 2012 Oct 25. Review. PubMed PMID: 23104465.

13: Bowles DW, Kessler ER, Jimeno A. Multi-targeted tyrosine kinase inhibitors in clinical development: focus on XL-184 (cabozantinib). Drugs Today (Barc). 2011 Nov;47(11):857-68. doi: 10.1358/dot.2011.47.11.1688487. Review. PubMed PMID: 22146228.

14: Durante C, Russo D, Verrienti A, Filetti S. XL184 (cabozantinib) for medullary thyroid carcinoma. Expert Opin Investig Drugs. 2011 Mar;20(3):407-413.doi: 10.1517/13543784.2011.559163. Review. PubMed PMID: 21314233.